trips outside of chicago

• Search Search Please fill out this field.
• Current Issue
• Give a Gift Subscription
• Manage Your Subscription
• Sweepstakes
• Around the Midwest

25 Weekend Getaways Near Chicago

Midwest Living's experienced editors create best-in-class travel, lifestyle, food, home and garden content you won't find anywhere else. We're loudly, proudly Midwestern, and we're passionate about helping our audience explore and create through award-winning storytelling.

When you need a day trip from Chicago or a weekend getaway from the big city, you don't have to go far. These escapes—including Amish Country, Indiana; Galena, Illinois; and Lake Geneva, Wisconsin—are within a one- to three-hour drive and offer a variety of activities that will recharge your life.

Indiana Dunes: 54 miles southeast of Chicago

This stretch of Lake Michigan coastline offers wide sandy beaches, towering dunes, great birding, easy bike trails and interesting history. Head to neighboring Chesterton for creative burgers at the Octave Grill and a pleasant night at Dunes Walk Inn, a restored 1881 mansion.

Lake Geneva, Wisconsin: 80 miles northwest of Chicago

This resort town of 7,600 has draws for summer and winter. Hotels, resorts and restaurants hug the lakeshore. Most visitors loll on the beach or cruise the lake during summer, but you can also experience the warmth of its winter in January and February during the annual Winterfest .

Michigan's southwest shore: 70 to 150 miles east of Chicago

Towns like New Buffalo, St. Joseph, Benton Harbor, Holland, Saugatuck and Grand Haven provide pristine beaches, great shopping, lakeside restaurants and front-row view of sunsets over Lake Michigan. The most accessible section of this shore extends from the Indiana line 175 miles north to Ludington. How far you drive is up to you – each town has its own personality. Take a spin on the carousel at St. Joe, tour a working windmill in Holland or just stretch out on a beach - preferably with a view of a lighthouse.

Galena, Illinois: 163 miles west of Chicago

Shops and restaurants in century-old buildings have long attracted visitors to this town of 3,500. But take time to hike, cruise the river or ski the slopes, sip local wines, taste beer and ... do some shopping.

Mount Morris, Illinois: 100 miles northwest of Chicago

With its rolling terrain, state parks and preserves traversed by the mighty Rick and Mississippi rivers, plus biking and hiking trails crisscrossing the area, the Blackhawk Waterways region of northwest Illinois promises outdoor recreation bliss. The region also helped shape the childhood of our 40th president, whose boyhood home opens its doors to visitors.

Cedarburg, Wisconsin: 113 miles north of Chicago

A great weekend destination for both shoppers and history buffs, Cedarburg has a Main Street that's on the National Register of Historic Places and dozens of limestone buildings housing more than 70 boutiques, chocolate shops and restaurants. Explore the town's history at the General Store Museum and Kuhefuss House Museum, and admire handiwork at the Wisconsin Museum of Quilts and Fiber Arts .

Bloomington-Normal, Illinois: 130 miles southwest of Chicago

For theater-lovers, summertime means outdoor Shakespeare. But in downstate Illinois, that takes on a fresh new form. Want improv Shakespeare? Sing-along Shakespeare? Or just a performance of his classics? Starting in June, and running through mid-August, the Illinois Shakespeare Festival in Bloomington-Normal reveals its ode to the Bard. Other draws to the area: Bloomington's restored 1800s buildings house farm-to-table restaurants, shops and live-music venues. Inside the three-story courthouse, a museum highlights the area's historical treasures.

Madison, Wisconsin: 147 miles northwest of Chicago

This town embraces the quirky and classy in its arts, museums, shops, dining venues and outdoor activities. Even its farmers market is a Bohemian rhapsody of local produce, entertainment, art and political activism on the state capitol square. Wander the paths and trails at Olbrich Botanical Gardens or the University of Wisconsin Arboretum ; admire the art at Chazen Museum of Art or the Madison Museum of Contemporary Art ; take a leisurely cruise around Lake Mendota or Menona; and be sure to work up an appetite-Madison's 600-plus restaurants offer something for every taste.

Rockford, Illinois: 90 miles west of Chicago

Illinois' third-largest city spent years watching travelers whiz by on Interstate-90 on their way east to Chicago. Now, thanks to a revitalized downtown, an emerging foodie scene, new cultural attractions and beautiful public gardens, word is getting out: You'd be crazy not to stop. The tranquil Anderson Japanese Gardens is just one of the draws to the area.

Fox River Valley, Illinois: 60 miles west of Chicago

An hour west of Chicago's Loop, the Fox River provides a soothing backdrop to towns brimming with indulgent eats, stores housed in historical homes and posh places to stay. Three towns along the winding river offer restful diversions with a nod to history: Catch a household name playing at St. Charles' historical Arcada Theater, or just 3 miles south, explore Geneva's shopping district, where boutiques fill preserved storefronts. And just minutes from Oswego's charming Main Street-with brick-paved sidewalks-is a family-run winery.

Milwaukee: 93 miles north of Chicago

Art, music and food festivals fill the calendar, and the compact downtown has just as diverse offerings. Watch the Milwaukee Art Museum's striking Quadracci Pavilion open and close its "wings"; catch the Milwaukee Brewers in Miller Park ; tour the Pabst Mansion ; or take a simulated motorcycle ride at the Harley-Davidson Museum .

Amish Country, Indiana: 110 miles east of Chicago

In tiny Nappanee, an Amish man parks his buggy by a gas pump, a living metaphor for the way new and old coexist in northern Indiana. Some people come here for classic Amish Country : 31 kinds of pie at Das Dutchman Essenhaus , hand-sewn gifts and homemade jellies at Little Helpers Quilt Shop , treasure-hunting at the Shipshewana Flea Market . But towns like Goshen, Middlebury and Elkhart also are modern communities.

Champaign-Urbana: 140 miles south of Chicago

Great outdoors, grown-up eats and classic clubs make these two cultured cities especially appealing in the summer when University of Illinois students head home. Grab a cheesy bite of nostalgia at Papa Del's Pizza or enjoy more upscale fare at Miga ; take time to admire the works at Krannert Art Museum and Spurlock Museum ; go for a stroll at the University of Illinois arboretum or Allerton Park and Retreat Center .

Starved Rock State Park, Illinois: 100 miles southwest of Chicago

Starved Rock State Park is a remarkable pocket of land along the Illinois River that includes 18 sandstone canyons, 14 waterfalls; abundant wildlife and birds; Belle of the Rock paddleboat excursions; and guided hikes, special events and interpretive programs. Spend the night in rooms or cabins (and enjoy a hearty meal) at Starved Rock Lodge , built in the 1930s by the Civilian Conservation Corps. If you're up for more exploration, also visit neighboring Matthiessen State Park , where 5 miles of trails carve into the mile-long canyon, passing rocks, waterfalls and beautiful, sometimes dizzying, vantage points.

Zion, Illinois: 50 miles north of Chicago

Zion is located in Lake County , which bridges the gap between Chicago's Cook County and the Wisconsin border with family attractions and nature trails. The area is home to Illinois Beach State Park , Volo Auto Museum and The Chocolate Sanctuary . For more fun, be sure to visit Six Flags Great America .

South Bend, Indiana: 95 miles east of Chicago

Though it's home to the Fighting Irish, it's not all football in South Bend. The St. Joseph River provides a great place for water sports and serves as a sparkling backdrop for a weekend of shopping and dining in the hometown of the University of Notre Dame.

Turkey Run Inn, Indiana: 150 miles south of Chicago

Sitting on a rocking chair on a veranda at Indiana's Turkey Run State Park inn feels surprisingly like taking refuge deep in the forest. The only sounds? Wind rustling through the trees. Owls hooting. Squirrels chattering. Brooks babbling. Maybe that's why quiet types flock here-bird-watchers, hikers and history buffs eager to explore Parke County and its covered bridges.

Grand Rapids, Michigan: 175 miles northeast of Chicago

Inspiration flows on both sides of the Grand River, particularly near downtown . Grand Rapids' ArtPrize extravaganza every other fall is part art walk, part city tour and and entirely vacation-worthy. But there's plenty to see at other times of the year, too, including the Frederik Meijer Gardens and Sculpture Park , Frank Lloyd Wright's Meyer May House and the Gerald R. Ford Presidential Library and Museum .

Elkhart Lake, Wisconsin: 150 miles north of Chicago

Sun, sand and...race cars? Most people come here for quiet weekends of swimming, sunning, boating and water-skiing in the crystal-clear lake , but the legendary Road America course is popular with amateur racers and their fans. Nearby Kettle Moraine State Forest also offers outdoor rec of another type with trails for biking, hiking and running. Round out the weekend with a stay in one of the area resorts such as the Osthoff.

Lake Mills, Wisconsin: 125 miles northwest of Chicago

Famous for The Ephraim Pottery Studio and Gallery , a getaway to Lake Mills also offers plenty of outdoor recreation on Rock Lake, the Zeloski Marsh and the Glacial Drumlin Bike Trail, as well as a cozy Arts and Crafts style B&B. Snack on crackers and sip wine at Lewis Station Winery, and don't miss the old-fashioned James J. Chocolate Shop.

Glencoe, Illinois: 15 miles north of Chicago

Glencoe is one of the few cities bordering Chicago along Lake Michigan. The communities of the North Shore seem farther from the bustle of downtown, thanks to abundant green spaces, including the Chicago Botanic Garden . Make sure to visit to Grosse Point Lighthouse during sunset in Evanston and take a walk along the Green Bay Trail between Winnetka and Highland Park.

Apple River Canyon State Park, Illinois: 146 miles west of Chicago

Every day, hundreds of drivers speed past the turnoff on US-20 for Apple River Canyon State Park , bound for getaways in Galena. Those travelers admire the view from the car, not realizing that if they wanted a peek at one of the area's few remaining secrets, they should turn north on Canyon Park Road west of Stockton and drive for just 7 miles. The 297-acre Apple River Canyon State Park offers quiet amid the woods along Apple River. Hike the bluffs. Look for fossils. Listen for wildlife. Fish the river—and let the others head to Galena.

Beloit, Wisconsin: 96 miles northwest of Chicago

This area is famous for its supper clubs that serve nostalgia and hearty portions. It all goes down easily with an old-fashioned drink.

Midewin National Tallgrass Prairie: 60 miles southwest of Chicago

Experience landscape that once rolled across the Midwest like an ocean at this restored prairie. Spot birds, hear frogs, hike and bike, see wildflowers and unwind among the 19,000 acres at Midewin National Tallgrass Prairie.

Woodstock, Illinois: 60 miles northwest of Chicago

It's just a train ride from Chicago, but Woodstock feels anything but suburban. The historic town square (famously featured in Groundhog Day ) is adorable, with great home decor shops and a cozy bookstore. Come for the summer activities or the annual Groundhog Day Festival in early February.

Protect Your Trip »

24 Top Weekend Getaways From Chicago

From beaches to ballparks and trails to rails, explore top breaks from the Windy City.

Getty Images

Hike along Michigan's Sleeping Bear Dunes National Seashore on your next weekend getaway from Chicago.

Known as the birthplace of the skyscraper, Chicago is home to award-winning restaurants , top sports teams and prized cultural treasures. But when you need a break from the excitement of the nation's third largest city, there are countless getaways within easy driving distance. You can explore rural Illinois or enjoy neighboring Indiana, Wisconsin, Iowa or Michigan all within a weekend. Whether you're planning a romantic getaway to a small-town bed-and-breakfast or a family-friendly trip to a water park resort, these nearby Midwest destinations will relieve the stress of big city life.

(Note: Some of the following activities, attractions and locations may be affected by the COVID-19 pandemic. New policies may be in place, including capacity restrictions, reservation requirements or mask mandates. Check with the Centers for Disease Control and Prevention, the U.S. Department of State and local tourism boards before traveling.)

Best Weekend Getaways from Chicago:

About two hours or less:, fox river valley, illinois, harbor country, michigan, st. joseph, michigan, milwaukee, wisconsin, south haven, michigan, starved rock state park, illinois, gurnee, illinois, wilmot mountain, wisconsin, lake geneva, wisconsin, grand geneva resort & spa, wisconsin, about three hours or less:, turkey run state park, indiana, the american club resort hotel, kohler, wisconsin, whistling straits golf course, sheboygan, wisconsin, saugatuck, michigan, wisconsin dells, wisconsin, about four hours or less:, parke county, indiana, galena, illinois, dubuque, iowa, and the field of dreams, ann arbor, michigan, madison, wisconsin, about five hours or less:, traverse city, michigan, louisville, kentucky, st. louis, missouri, a quick flight:, minneapolis – st. paul, minnesota.

Located along the picturesque Fox River on the western outskirts of Chicago lie the small towns that make up Illinois' Fox River Valley. Stretching from the village of Antioch in the north to Ottawa – the gateway to Starved Rock State Park – in the south, this area is an ideal daytrip from the Windy City. Go biking, hiking and cross-country skiing along the 32-mile Fox River Trail or rent a kayak for paddling on the Fox River. In addition to outdoor pursuits, unique cultural attractions abound, including Broadway productions and musical events in Aurora's historic and beautifully restored Paramount Theatre. Visitors rave about its exquisite decor and top-notch performances, applauding the Paramount for offering Broadway-caliber performances at Main Street prices. If you choose to overnight in the Fox River Valley, the Herrington Inn & Spa , which overlooks the Fox River in the small town of Geneva, would make for a romantic getaway.

New York has the Hamptons; Boston has Cape Cod . The summer playground for Chicagoans consists of eight glistening lakeshore towns dotting the coastline of southwest Michigan, collectively known as Harbor Country. Here you'll find beaches, orchards and plenty of outdoor activities. At the southern end of Harbor Country, just over the Michigan-Indiana state line and about 70 miles from Chicago's downtown loop, New Buffalo lures Chicagoans with its casual beach vibe and proximity. Families line up for burgers at The Stray Dog, but only adults can head up to the rooftop bar and patio. Patrons praise The Neighborhood Hotel Grand Beach for its modern design combined with cozy common areas, fire pits, ping pong tables and board games; they also appreciate the short walk to the beach and the heated pool.

[Read: The Top Things to Do in Michigan .]

Families will want to make the scenic 25-mile drive from New Buffalo north through the Harbor Country towns of Union Pier and Lakeside, past grand lakefront estates and bucolic farms, to St. Joseph, commonly called St. Joe's. The family-friendly Silver Beach Pizza is housed in St. Joe's former train depot, with diners saying it's well worth what can be a half hour wait for the amazing pizza. Across the street is the restored 1910 Silver Beach Carousel, a great option for passing the time while waiting for your table if you've got kids along. St. Joe's offers visitors the chance to step back in time with a beach, pedestrian-friendly downtown, boutiques and old-fashioned chocolate shops. One of St. Joe's more unique shops is Third Coast Surf, where you can rent a surfboard and sign up for surfing or sandboarding lessons. Not expecting a surf shop in the Midwest? Visitors are often surprised when they first see Lake Michigan, known to Midwesterners as the Third Coast: It resembles an ocean more than a lake.

Located about 80 miles north of Chicago on Lake Michigan is the Brew City of Milwaukee , which boasts more than 200 breweries, museums, festivals and the Harley-Davidson Museum . As this city is home of the Milwaukee Brewers baseball team, no trip is complete without getting a taste for Milwaukee's beer heritage. Visitors give Lakefront Brewery tours high marks for entertaining guides, extensive selection, riverfront views and its popular Beer Hall restaurant with live music on Fridays. Families will enjoy the lakefront museum campus, which includes the Discovery World science museum and Betty Brinn Children's Museum, while culture lovers can visit the architecturally stunning Milwaukee Art Museum when the building's "wings" open and close several times a day. Motorcycle enthusiasts will be in hog heaven at the modern steel-and-glass Harley Davidson Museum, which celebrates the machine invented in Milwaukee that's come to symbolize the freedom of America and the open road.

Winters are harsh, so summer is one endless celebration, with a multitude of neighborhood festivals, outdoor concerts and ethnic celebrations – check out German Fest at the end of July, honoring the city's largest immigrant group. Summer excitement reaches a crescendo at the end of June with Summerfest, the world's largest music festival. After a day of sightseeing or revelry, a top lodging choice is Milwaukee's stately grand dame, the historic Pfister Hotel , offering Gilded Age elegance alongside 21st-century amenities like a pool with panoramic city views and a popular top-floor cocktail bar.

[See more of Milwaukee:  Things to Do  | Hotels  |  Photos ]

South Haven is a fun-loving beach town with a population that swells in the summer – especially in August for the National Blueberry Festival, since this Michigan destination claims to be the blueberry capital of the U.S. About 110 miles from Chicago, you'll hear a lot of Jimmy Buffett playing in the bars and restaurants of this laid-back boating town where the harbors take center stage. Kick off your visit by learning about the area's rich Great Lakes boating history at the Michigan Maritime Museum.

Along with its seven public beaches – some of the best beaches in Michigan – and iconic red lighthouse, South Haven also has a pedestrian-friendly downtown filled with unique shops and restaurants. Climb aboard the stationary Idler Riverboat, where casual dining combines with world-class waterfront views. Clementine's is another local favorite, as is Captain Lou's, which serves fresh perch and live music on the weekends. For a romantic getaway, consider Inn at the Park, a bed-and-breakfast one block from Lake Michigan: Guests praise the beautiful decor and sumptuous breakfasts, using locally grown blueberries. Travelers also love Yelton Manor Boutique Hotel for its manicured gardens, spectacular sunset views of Lake Michigan and proximity to town.

Looking for an active adventure? Only about 100 miles southwest of Chicago, this wilderness known for its deep sandstone canyons and waterfalls is perfect for daytrips – though with 18 canyons to hike, there's plenty to keep you busy for a whole weekend. Walking along bluffs that lead to scenic lookouts over the Illinois River makes visitors feel immediately transported out of the flat Midwest heartland. Starved Rock State Park can be a weekend escape any time of year, but spectacular fall foliage makes it a favorite getaway for autumn in particular.

Starved Rock State Park has its own historic lodge with top-notch cabins , but kids may prefer going across the street to the family-friendly Grizzly Jack's Grand Bear Resort, with its massive water park, mini-golf, indoor arcade and Northwoods decor. Camp Aramoni is a great choice for a romantic getaway, with luxury glamping in safari tents outfitted with hardwood floors, air conditioning and heating, and full bathrooms with showers. Nightly stays include chef-prepared farm-to-table dinner and breakfast using produce grown in on-site gardens that guests are welcome to visit. End your day at Camp Aramoni's repurposed Airstream trailer that's been turned into a bar.

Looking for high-adrenaline family fun? About 35 miles north of Chicago, just south of the Wisconsin border, lies the village of Gurnee, home to the Six Flags Great America amusement park . Thrill-seekers will love the 17 heart-stopping roller coasters, but dozens of other rides mean you'll also find plenty for younger kids. Reluctant riders who want to steer away from high-speed coasters and intense drop rides can also enjoy the park's shows and other entertainment. On a hot day, plunge down steep waterslides or splash around the wave pool at Six Flags' 20-acre Hurricane Harbor water park. When it gets cold, a favorite local pastime is a stroll around Gurnee Mills, an outlet mall housing more than 170 stores.

Continue your Gurnee adventure with a stay at the Northwoods-themed Great Wolf Lodge, the most family-friendly hotel option in this destination. Guests say this water park resort makes even adults feel like kids again and rave about the endless family-friendly amenities, which include bowling, mini-golf, a ropes course and arcade – and, of course, the massive water park.

Since 1938 Wilmot Mountain has drawn visitors seeking wintertime leisure in the Midwest. About 25 miles northwest of Gurnee, just over Wisconsin's state line, Wilmot Mountain Ski Resort makes for a great cold-weather attraction when Six Flags is closed. The big-name Vail Resorts purchased Wisconsin's little ski hill in 2016 and rolled out plenty of upgrades, from improving terrain parks and snowmaking to adding chairlifts and elevating the dining experience. Enjoy winter sports over a variety of terrain at this alpine destination, whether you're looking to ski, snowboard or snow tube. There's no on-site lodging, but Gurnee's Great Wolf Lodge is still a relatively short drive away.

[Read: The Top Things to Do in Wisconsin .]

This Wisconsin resort city makes for an idyllic weekend or daytrip. About 70 miles northwest of Chicago, Lake Geneva is described as the " Newport of the Midwest" because of its opulent lakefront mansions. You can come surprisingly close to these impressive residences by ambling along the Geneva Lakeshore Path, a rustic 25-mile walkway that encircles the lake, cutting right through the backyards of magnificent mansions and second homes. Amazingly, there aren't any "No Trespassing" signs to scare away walkers; just beware the path is not intended for strollers, roller blades or bikes, since you'll have to maneuver past steps and other obstructions. When you've finished your stroll, a lakefront cruise is another fun way to enjoy this city. Visitors give Lake Geneva Cruise Line excellent reviews for being informative and entertaining. A variety of daily cruises are offered, but one of the most unique is the mail delivery cruise. As Lake Geneva is one of the few remaining places in the U.S. where mail is still delivered by boat, about 75 lakefront homes receive their U.S. mail service via boat – and passengers are invited to come along for the ride.

Consider a stay at the Abbey Resort, the only full-service resort directly on the shores of Lake Geneva, during a summer visit. This lodging option offers complimentary adult and kids bikes, ideal for use on the Lake Geneva Bike Path, which connects many of the resort town's amenities. The trail has five unique, color-coded segments, making it easy to find your way around. Things quiet down a bit in the fall, when the vibrant autumn colors set a serene scene.

[Read: The Best Midwest Vacations for Families .]

Tourists descend on Lake Geneva's charming downtown shops and restaurants in the summer, but the town has plenty to do year-round. One of the best winter attractions in this city is the Grand Geneva Resort & Spa , whose modest ski hill has three chair lifts, 20 runs and a terrain park. Grand Geneva Resort also has access to 5 miles of wooded trails for cross-country skiing and offers a limited number of ski rentals. Kids will love overnighting at Grand Geneva's family-friendly Timber Ridge Lodge and Waterpark for indoor aquatic fun while adults relax at the spa. Time your winter visit to coincide with Lake Geneva's Winterfest so you can observe one of the country's biggest snow sculpting competitions.

Turkey Run State Park is the crown jewel of Parke County and one of the Hoosier State's oldest and most popular state parks. Eleven trails ranging from a half-mile to 2 miles wind through rugged ravines surrounded by the park's signature sandstone cliffs – providing Midwest hiking at its best. Turkey Run Inn, a popular lodging option situated within the park, is appreciated by guests for its friendly staff and cozy atmosphere. There's an indoor pool and plenty of public sitting areas with fireplaces, whether you want to play a board game or read a book. Choose from rooms within the historic lodge or the adjacent cabins. Even if you don't stay at Turkey Run Inn, you can still enjoy its restaurant, The Narrows, which diners recommend for the catfish dinners as well as the fried biscuits and hot apple butter.

Most have never heard of this tiny town 140 miles north of Chicago, but Kohler is home to Wisconsin's only hotel to receive AAA's highest five diamond rating. The American Club Resort Hotel – part of the Destination Kohler Resort – is still owned by the family who built it: The Kohlers are best known for high-end plumbing and bathroom fixtures. The American Club's luxurious Kohler Waters Spa specializes in hydrotherapy, giving guests a chance to experience all the legendary bath and shower products Kohler is known for. Should you want to recreate that luxury spa experience in your own bathroom at home, a few steps away from the spa is the sleek, multistory Kohler Design Center, filled with model bathrooms and design ideas sure to give most of us bathroom envy. Amid your self-care ventures in Kohler, enjoy plenty of outdoor activities. Fall brings a boisterous bounty of color to this rural area, while winter experiences at The American Club include ice skating, curling, snowshoeing and cross-country skiing across miles of trails that wind through woodlands and meadows.

Ten miles from American Club Resort Hotel sits the Kohler-owned Whistling Straits Golf Course, which some golfers describe as reminiscent of the legendary Pebble Beach . Whistling Straits ranks among the top public courses in the country and has hosted 2021's Ryder Cup and three PGA championships. The two Pete Dye-designed courses at Whistling Straits offer stunning views of Lake Michigan or rolling green hills. Golfers will feel transported to Ireland's tranquil grassland or its rugged coastline as this course winds its way along the bluffs and dunes overlooking Lake Michigan.

It's easy to see why Saugatuck is one of the best places to visit in Michigan . Nicknamed the Art Coast of Michigan, this hip resort town about 130 miles from Chicago is stocked with galleries, boutiques, excellent dining and beaches. Perhaps surprisingly for a town of less than a thousand people, Saugatuck is also known for its lively nightlife and for being an LGBTQ-friendly destination. Take a seat at the counter of the century-old Saugatuck Drug Store and you'll get a taste of the town's more traditional side, served up via a classic malt or ice cream soda. Visitors are in for another nostalgia trip when you board the chain ferry: Operating since 1838, it claims to be the only remaining chain-driven ferry in the U.S., transporting passengers across the Kalamazoo River between downtown and Oval Beach. After disembarking on Oval Beach, active beachgoers love climbing the 302 steps to the top of Mount Baldhead – known as Mt. Baldy – and getting a bird's eye view of the area. Overlooking Lake Michigan, Saugatuck's Lake Shore Resort is applauded by patrons for its breathtaking views and many complimentary amenities, including bikes, kayaks, yoga and a heated pool.

About 190 miles northwest of Chicago is the ultimate Midwest family getaway: the "Waterpark Capital of the World." If traveling with kids to Wisconsin Dells, stay at one of the immensely popular water park resorts , such as the flagship property of Great Wolf Lodge. Guests appreciate the original Great Wolf Lodge for its signature Northwoods decor, endless amenities and the feeling of being in a tropical paradise year-round.

Beyond its myriad indoor and outdoor water parks, Wisconsin Dells boasts a wide variety of kid-friendly entertainment options, from zip lines to animal parks. Catch a performance at the Palace Theater, which offers everything from concerts to comedy shows to children's plays and Broadway-style productions; some theatergoers swear there isn't a bad seat in the house. More fun for the whole family can be found at the Rick Wilcox Magic Theater shows, which wow audiences with both humor and illusions that keep you guessing. Want to escape the indoor attractions for a natural one? Head over to Mirror Lake State Park for a scenic hike along a tranquil, no-wake lake set among sandstone bluffs. Pontoon boats, kayaks and stand-up paddleboards are available to rent here.

[Read: The Top Things to Do in Wisconsin Dells .]

Billing itself as the covered bridge capital of the world, Parke County, Indiana – about 160 miles south of Chicago – maintains 31 of these Instagram-worthy symbols of a bygone era. Visitors descend on the area every October for the Parke County Covered Bridges Festival, Indiana's largest annual festival. The popular biker bar Thirty Six Saloon is a family-friendly roadhouse in Rockville, the town where the popular fall festival is headquartered. Kids may be mesmerized by Thirty Six Saloon's vast collection of taxidermy, with animals from the region mounted throughout the restaurant. Diners compliment everything from the burgers and ribs to the fish sandwiches and unique decor. Another popular culinary option is the tenderloin sandwich at the Mecca Tavern in Mecca. Parke County's oldest tavern overlooks Mecca's historic schoolhouse and covered bridge. Locals and visitors alike say stopping by Wheelhouse Donuts is another must: This adorable bakery lets you design your own doughnut.

About 150 miles west of Chicago, in the northwest corner of Illinois, the charming Mississippi River town of Galena regularly makes national lists of best small towns . Its elegant dining, historic sites, quaint shops and bounty of bed-and-breakfasts make Galena an excellent choice for a romantic getaway. Because the glaciers that flattened most of the Midwest didn't reach here, the pastoral farmland is hillier, perfect for a Sunday drive. The 19th-century buildings in this old mining town have been painstakingly preserved, with 85% on the National Register of Historic Places – including the Ulysses S. Grant Home State Historic Site, a residence gifted to the nation's soon-to-be 18th president in 1865 by Galena citizens.

One memorable overnight option would be a stay at the former county jailhouse – now the luxurious Jail Hill Inn. For a more romantic atmosphere, the Goldmoor Inn is beloved by guests for its stunning views of the Mississippi River, in-room fireplaces and two-person hot tubs. Galena is gorgeous any time of year, with plenty of travelers drawn here during harvest time for apple and pumpkin picking amid the abundance of fall colors. Winter brings its own charm with shops along Main Street resembling something out of a Norman Rockwell painting. The small town also houses a popular old-school ski resort: Guests say Chestnut Mountain Resort's decor and amenities are a bit dated, but its 19 ski runs provide scenic views of the river below.

Head 170 hundred miles west of Chicago, cross the Mississippi River, and you'll be in Dubuque, Iowa. Get a feel for how important the river is here by visiting the National Mississippi River Museum and Aquarium, or take a ride on a riverboat for another scenic way to experience the Mississippi. Visitors give the Celebration Belle river cruise high marks for being fun, informative and affordable. Another must-see attraction is Fenelon Place Elevator, a steep funicular railway providing fabulous views of the surrounding area. History lives on at the elegant Hotel Julien Dubuque, which guests compliment for its charm and friendly service. Baseball fans will want to make the additional 25-mile drive west to the town of Dyersville to explore the Field of Dreams, one of the best tourist attractions in the U.S. Play on the baseball diamond and tour the home where the movie "Field of Dreams" was filmed.

About 230 miles northeast of Chicago, Ann Arbor is a quintessential college town, filled with independent bookstores and great live music. University of Michigan alumni are a proud bunch – and not just on game days, when they march clad in blue and yellow to what's known as The Big House, the largest sports stadium in the country. Ann Arbor also scores an A when it comes to food and culture. The world-class University of Michigan Museum of Art displays works by Picasso, Monet and Warhol. A few blocks away on Liberty Street is the edgier public art canvas known as Graffiti Alley, just steps from the historic Michigan Theater and State Theatre, which delight visitors with film screenings, festivals and live music throughout the year (as long as you follow the theaters' COVID-19 regulations ). A pastrami sandwich at Zingerman's Deli is a 40-year tradition, but if you're hungry for a more budget-friendly option head to Frita Batidos and take a seat at one of the communal tables for Cuban-inspired street food. Hit the books at Literati, a beloved independent bookstore. A fun hotel choice is Graduate Ann Arbor with its University of Michigan-themed decor.

[See more of Ann Arbor: Things to Do | Hotels | When to Visit | Photos ]

About 140 miles northwest of Chicago, Madison is more than just a cool college town: It's also the capital of Wisconsin. No trip here is complete without visiting the beautiful, white-domed Wisconsin state Capitol building; free tours are given throughout the day. Madison's isthmus location on a narrow strip of land between two lakes means waterfront biking and hiking trails abound. Foodies will also get their fill at Fromagination, a cheese lover's paradise popular with Wisconsin cheeseheads as well as out-of-town visitors. Located across from the Capitol, this delightful cheese shop features dozens of one-of-a-kind artisanal Wisconsin varieties. If visiting Madison between April and November, head to Capitol Square on Saturday morning for the Dane County Farmers' Market, the country's largest producer-only farmers market. The 72-room, collegiate-themed Graduate Madison hotel is an easy walk to campus, dining, shopping and nightlife. Decorated in the University of Wisconsin colors of red and white, the hotel gets high marks from guests for its nostalgic decor and artwork, including collages of political buttons, a nod to the town's legacy of social activism.

[See more of Madison: Things to Do | Hotels | When to Visit | Photos ]

Those who have more time could leave the bright lights of Chicago for the serenity of Michigan's Traverse City to visit Sleeping Bear Dunes National Lakeshore and its 64 miles of pristine coastline and mountains of sand dunes. Traverse City is about 300 miles from Chicago, but you'll be rewarded with breathtaking beaches, peaceful hikes, top-notch cuisine and the added perk of what's considered the " Napa Valley of the Midwest": the 24 wineries of the Leelanau Peninsula Wine Trail. When the temperatures drop and the snow arrives, a great winter weekend getaway involves cross-country skiing in Pere Marquette State Forest or the Leelanau Trail, which runs from Traverse City to Suttons Bay. Traverse City and northern Michigan are also filled with summer lake resorts: Top options include Lake Leelanau's Fountain Point Resort, the upscale Homestead Resort and the all-inclusive White Birch Lodge in nearby Elk Rapids. With White Birch known for its water sports program, teens and tweens will love water-skiing, tubing and ending the day swapping adventures with new friends around a beach bonfire.

[See more of Traverse City: Things to Do | Hotels | Tours | When to Visit | Photos ]

Best known as the location of the Kentucky Derby, Louisville sits 300 miles south of Chicago and has a whole lot more going on than just horse racing. About 95 percent of the world's bourbon is made in Kentucky ; for a taste of the state's signature liquor, head to downtown Louisville's historic Whiskey Row. Here you'll find distilleries, unique restaurants and live music. Topping any sports lover's itinerary should be a visit to the Louisville Slugger Museum and the Muhammad Ali Center , which visitors applaud for honoring the boxer's life, faith and humanitarian service. Art lovers would enjoy staying at the 21C Museum Hotel Louisville , which houses its own contemporary art museum.

[See more of Louisville: Things to Do | Hotels | Photos ]

About 300 miles southwest of Chicago, just over the Illinois border along the Mississippi River, sits this Missouri city. St. Louis is well worth a weekend trip for its plethora of restaurants, breweries and cultural treasures. Nicknamed the Gateway City for its iconic Gateway Arch , St. Louis gives travelers the chance to take a tram ride to the top of this engineering marvel. After getting a bird's-eye view of the surrounding area, head over to the nearly 1,300-acre Forest Park , site of the 1904 World's Fair, now home to the Saint Louis Zoo and several museums. Music lovers can't miss the National Blues Museum, which sings the praises of that melancholy American music form. If you find yourself in need of more music lessons, make your way to the Scott Joplin House State Historic Site, where the king of Ragtime lived. After a busy day sightseeing, Drury Plaza Hotel St. Louis at the Arch makes a good place to rest. Guests rave about the unbeatable value of the hotel's free breakfast and happy hour with complimentary hot food and drinks.

[See more of St. Louis: Things to Do | Hotels | When to Visit | Photos ]

The Twin Cities of Minneapolis − St. Paul straddle the Mississippi River, about 450 miles northwest of Chicago, with Minneapolis as Minnesota's most populous city and St. Paul as the state capital. Minneapolis is known as a city of lakes, but visitors also like to walk along the riverfront, taking in the magnificent Mississippi. Groundbreaking pop musician Prince was born in Minneapolis; now his legacy lives on at Paisley Park, a sprawling complex in the nearby town of Chanhassen that was once the artist's studio and home. Millions more travel here to visit the largest mall in the Western hemisphere, Mall of America , located in the nearby suburb of Bloomington. As much an entertainment complex as a retail center, this mall houses the indoor amusement park Nickelodeon Universe, a highlight for kids. Guests give Minneapolis' Hewing Hotel stellar reviews for its character, charm and stunning views from the rooftop lounge.

[See more of Minneapolis − St. Paul: Things to Do | Hotels | When to Visit | Photos ]

You might also be interested in:

• The Best Weekend Getaways
• The Top Romantic Getaways in Illinois
• The Top Romantic Getaways in Wisconsin
• The Top Romantic Getaways in Michigan
• The Top Romantic Getaways in Ohio
• The Top Fall Weekend Getaways
• The Top Travel Neck Pillows
• The Top Travel Backpacks
• The Top Duffel Bags

Tags: Travel , Midwest Vacations , US Vacations

World's Best Places To Visit

• # 1 South Island, New Zealand
• # 4 Bora Bora

If you make a purchase from our site, we may earn a commission. This does not affect the quality or independence of our editorial content.

You May Also Like

Flight canceled or delayed what to do.

Amanda Norcross April 26, 2024

The Best Beach Hats

Megan Johnson and Sharael Kolberg April 26, 2024

The Best Florence Tours

John Rodwan April 25, 2024

The 9 Best Louisiana Swamp Tours of 2024

John Rodwan April 24, 2024

How Much Does a Cruise Cost?

Gwen Pratesi April 24, 2024

The Best Whale Watching in Cape Cod

Lyn Mettler April 24, 2024

Best Whale Watching Tours in Maine

Marisa Méndez April 23, 2024

The Best Wineries in Napa Valley

April 23, 2024

The Best East Coast Beaches

April 19, 2024

The Best Carry-on Luggage

Erin Evans , Rachael Hood , Catriona Kendall , Amanda Norcross and Leilani Osmundson April 17, 2024

10 Essential Destinations For Day Trips And Weekend Getaways From Chicago

If you're looking to get out of the city for a minute, whether for nature, small-town living, or just a different city, these are our favorite places to go!

As our thriving metropolis moves into the glorious spring and summer temperatures, riverside bars, lakefront beaches, and our plethora of parks all blossom with jubilance. But at the same time, our urban jungle can sometimes become too much, and weekend getaways from Chicago are much-needed. While Lake Michigan offers respite from the summer heat, there’s peace found in escaping the city clamor during its more restless months.

As unique as Chicago is, getting out of the city once in a while to explore new pastures, even just for a day or two, is good for the mind, body, and soul. To give readers some ideas of accessible weekend getaways from Chicago , we’ve picked out our favorite places a short drive away that would make for superb day trips and weekend destinations as they all begin to flourish in the coming months.

1. Starved Rock State Park, Illinois

If you are cooped up and want to escape into nature for fresh air, look no further than Starved Rock State Park in Illinois. Added to the National Register of Historic Places in 1998, Starved Rock is an incredible spectacle offering over 13 miles of hiking trails , 14 waterfalls , and 18 glorious sandstone canyons, all less than two hours outside Chicago.

Currently, the Starved Rock State Park and Starved Rock Lodge are open, in addition to the Veranda, The Starved Rock Cafe, and Trailheads Concessions for food and drinks. Steeped in history and beauty, Starved Rock State Park offers a wonderful break for outdoor enthusiasts and those looking for a nonchalant trip outside the city.

📍98 miles outside Chicago

2. Indiana Dunes State Park, Indiana

However, our favorite spot across the eastern border has to be Indiana Dunes State Park. Here you’ll find one of the best views of Chicago’s sensational skyline imaginable. With 2,000 acres of sand and shore, there is so much to explore and plenty of space to enjoy. You can bound up mountainous dunes (and then roll back down them), go spelunking in one of Indiana Dunes State Park’s many caves , take a moment to relax on the beaches of Lake Michigan, and much more.

All of the park’s inns, restaurants, all nature preserves, forest, fish, and wildlife areas are open for you to explore this spring and summer!

For real-time updates on what’s available at the Indiana Dunes State Park, follow Indiana State Parks on their social media.

📍50 miles outside Chicago

3. Galena, Illinois

A little journey to the top western corner of Illinois, but still just a one-tank trip, and you’ll find Galena. Listed on the National Register of Historic Places, the city is renowned for its rich history, charming 19th-century architecture , rolling hills, and numerous resorts. It’s a quaint but enjoyable historic getaway named after the mineral galena, which was the reason for the first major mineral rush in the United States.

It’s one of our favorite small towns near Chicago , where visitors can enjoy views of three states from Horseshoe Mound, just outside of Galena. At the same time, the Great Galena Balloon Race happens yearly and offers the chance to enjoy the magic of more than 20 hot air balloons, three races, a night glow extravaganza, bounce houses, live music, and much more at a spectacular three-day event.

📍150 miles outside Chicago

4. Lake Geneva, Wisconsin

Lake Geneva has long been a vacation haven for Chicagoans. The resort city features 21 miles of beautiful shoreline with amazing beaches and a sea of water activities. Whether you’re looking to kick back and relax at a resort, gear up for the many outdoor activities the city has on hand, or relish in its variety of restaurants, retailers, and nightlife attractions, Lake Geneva has what you’re looking for.

📍80 miles outside Chicago

5. Rockford, Illinois

With the exception of Gary, Indiana — every one of these destinations will give you a chance to step back and relax. If relaxation is your intention, Rockford is one of your best bets. The city is flush with blooming gardens and a network of streaming rivers . Like Chicago, it boasts terrific eateries and fantastic amenities and attractions, such as the sublime Anderson Japanese Gardens. This award-winning landscape was named one of the highest-quality Japanese Gardens in North America by Sukiya Living Magazine.

📍89 miles outside Chicago

6. Milwaukee, Wisconsin

While it is the second-largest city on Lake Michigan’s shore behind Chicago, taking a drive up to Milwaukee provides a nice change of scenery but a similarly vibrant urban experience in another ethnically and culturally diverse city. Take your pick from the plethora of top-notch breweries around the city for the full taproom experience.

See what else is on tap in the city by checking out their amazing food, scenic drives, outdoor art, beaches, parks, and their famous Riverwalk, making it this part of weekend getaways from Chicago you need to check out. From the Harley-Davidson Museum to the Milwaukee Art Museum , there are also an array of great museums if you’ve spent too much time in Chicago’s many museums.

📍92 miles outside Chicago

7. Holland, Michigan

With this town’s dazzling display o f 4.5 million blooming tulips , it’s no wonder that Holland, Michigan made it on our weekend getaways from Chicago list. The town is rich in Dutch culture. Throughout the year, the town regularly holds a variety of parades in honor of its Dutch heritage. Visitors can explore wonderful Dutch cuisine , architecture, windmills, and art collections around the city. If you visit Holland, be sure to stomp by the DeKlomp Wooden Shoe & Delft Factory for the ultimate experience.

8. Door County, Wisconsin

Take your partner on a romantic getaway to Door County, Wisconsin. Door County is home to 300 miles of shoreline, acres of orchards, five state parks, and 11 historic lighthouses . Choose your lodgings in a bed & breakfast, log cabin, a cozy cottage, or do it big at a resort. Wherever you hang your hat at night, know there’s much to do during the day.

Explore the county’s beautiful parks , caves, and forestry, or voyage out to one of its islands by sea — whether by boat, kayak, or paddleboard — though the latter might take a minute. Go cherry-picking and finish the day with fine wine, local brew, or cider while dining down on home-cooked cuisine.

📍244 miles outside Chicago

9. Shawnee National Forest, Illinois

While it is certainly a bit of a trek to this spot on the opposite side of Illinois, the natural landscapes make it worth the trip of weekend getaways from Chicago. Shawnee National Forest is our state’s only national forest, spanning approximately 280,000 acres in Southern Illinois between the Mississippi and Ohio rivers.

It is home to some awe-inspiring natural landscapes , unique ancient rock formations, sprawling panoramic views, and breathtaking hikes. The 300-million-year-old sandstone rock formations known as The Garden of the Gods offer some of the most stunning scenery in Illinois and are one of the most photographed places in the state. The famous Observation Trail takes you through the abundance of natural beauty.

The forest is also home to some extraordinary caves, such as Ox-Lot Cave and the enormous 55ft wide cave overlooking the Ohio River by the name of Cave-In-Rock, which was once a refuge stronghold for frontier outlaws. There are plenty more natural spectacles like the monolithic 30 feet high and eight feet Pomona Natural Bridge extending 90 feet over a verdant ravine and numerous beautiful waterfalls like Jackson Falls to explore on a hot day. An abundance of camping spots means it’s an easy task for keen campers, but Shawnee Forest Cabins with Wi-Fi, hot tubs, and fireplaces, as well as rentable treehouses, offer memorable experiences.

📍309 miles outside Chicago

10. Gary, Indiana

A world away from the waterfalls of Starved Rock, but under two hours by car, we’d be remiss, not to mention the casinos in Indiana. If you are ready to roll the dice, drive to Gary, Indiana, to visit the Majestic Star Casino. There you’ll find six floors packed with all the classic casino games — poker, blackjack, baccarat, roulette, and a wide — in a whirling atmosphere of bright blinking lights, buzzing slots, and high-rolling energy.

The casino has been revamped since a return to normalcy following the pandemic and offers a cutting-edge experience with added safety and sanitary measures.

📍30 miles outside Chicago

[Featured image from Shutterstock]

TYPE IN YOUR SEARCH AND PRESS ENTER

North America Chevron

United States Chevron

Illinois Chevron

Chicago Chevron

Best Weekend Getaways From Chicago

By Nina Kokotas Hahn

All products featured on Condé Nast Traveler are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.

Chicagoans itching to travel right now should not underestimate the power of a great winter road trip, and not just because it may feel like the only safe option at the moment. In a break from the norm, we’ve found exciting places offering something fresh and surprising for the Midwest, making them well worth the drive. A fun, elegant cocktail experience, lakefront retreats that offer stunning views, snowy ski trips with plenty more to do off the slopes—it’s all available. Here are the best weekend getaways from Chicago .

(Editors note: Given the changing nature of the COVID-19 pandemic , the hours and accessibility of many venues are fluid and subject to change. Make sure to contact them before visiting.)

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.

LAKE FOREST, ILLINOIS

Distance from Chicago 33 miles

The Deer Path Inn

In less than 60 minutes by Metra or just over 30 minutes by car, find yourself feeling far from the city in this pretty Northshore town off of Lake Michigan. No doubt Lake Forest is fancy with its sprawling estates, Market Square, and upscale shops (check out the all-women-run Lake Forest Bookstore and Valentina boutique), and coveted waterfront views. Being here also puts you 20 minutes closer to the 385-acre Chicago Botanic Gardens , where the Japanese and dwarf confider gardens are especially sublime in winter.

Where to Stay

The main reason to go to Lake Forest now is a weekend away at the 57-room Deer Path Inn ( from $329 per night ), a fabulous, little-known gem that puts you in arm's reach of the shops and lake, and offers many experiences available only to guests. Opened in 1929 with the style of an authentic manor house, the elegant inn feels as storied and local as it does far-flung and English. Spacious, modern, and sophisticated rooms offer upscale amenities (think Frette linens and bathtubs that fill from the ceiling); recently, the inn began in-room delivery of its popular Afternoon Tea service, complete with a tower of tea sandwiches, petit fours, and tartelettes. Patio dining in the English Garden at Deer Path is scenic and doable in winter with heaters. Guests at the hotel can also reserve the inn’s hidden cellar for a new, private, and totally custom cocktail or wine tasting paired with dinner that's led by Deer Path’s fun and expert chief spirits officer, Jorge Centeno.

INDIANA DUNES NATIONAL PARK, IN

Distance from Chicago 49 miles

The dunes overlooking Lake Michigan at Indiana Dunes National Park

Drive just 60 minutes and find yourself surrounded by beauty in the 15,000-acre Indiana Dunes National Park , which packs in an astounding amount of botanical diversity thanks to its variety of lowlands, highlands, prairies, wetlands, forests, and Lake Michigan shoreline. Time your visit with cool winter conditions, when snow cloaks the park in white, and there’s a chance to see spectacular shelf ice formations on the water, not to mention you’ll get a far more secluded experience. Venture out on cross-country skis or snowshoes—the latter of which can be borrowed for free at the park’s Paul H. Douglas Center for Environmental Education. All of the park’s 50 miles of trails are available for winter activities, but opt for a one-mile loop or three-mile route on the Paul H. Douglas Trail, which takes you to the beach through a rolling black savannah, one of the rarest habitats in the country. Often confused with the national park, the two-acre Indiana Dunes State Park , immediately next door, is also open and admission is waived on weekdays in winter.

Nearby Chesterton offers a good location central to both parks, and interesting B&B’s are the way to go. Within walking distance to restaurants and shopping, Riley's Railhouse Bed & Breakfast ( from $140 a night ) is housed in a former New York Central style freight station and has rooms in real rail cars. The family-friendly DunesWalk Inn at the Furness Mansion ( from $125 a night—you can also rent the entire place out on Airbnb ) is another historic option that balances digs in an 1881 mansion with modern comfort, just a few minutes from the beach.

HARBOR COUNTRY, MI

Distance from Chicago 75 miles

A view of Lake Michigan from the Water's Edge house

Didn’t score a Michigan beach house last summer? Winter isn’t hot, but it’s a gorgeous and secluded time to experience the dramatic Lake Michigan coast from the comfort of a luxury beach home, most of which can be had now at low season rates. Take your pick of towns on the state’s south coast like Union Pier, New Buffalo, and little-known Harbert. Sans summer crowds, this is the time to stop at the harborside Stray Dog Bar & Grill . Even better, book an igloo for outdoor dining at small-batch Beer Church Brewing , try alfresco wine tastings at Round Barn Estate , or get takeout from Red Arrow Roadhouse (try the buffalo cauliflower and nachos) and locally made whiskey from the Journeyman Distillery to bring back home. As everyone does, give into the pull of the lovely Lake Michigan coast, where dune walks and sledding at Warren Dunes State Park should be high on your list.

Bluefish Vacation Rentals (from $100 a night ) is your best option for a well-curated assortment of homes throughout Harbor Country, plus the bonus concierge-like guidance of the local husband-and-wife team who run it, Jason and Erika Milovich. In winter, most of their homes can be had at low season rates and don’t require summer’s usual full week stay. The scenery can’t be beat in Harbert at three-bedroom Water’s Edge , a splurge-worthy find tucked into a forested bluff overlooking a private stretch of Lake Michigan shoreline; spend $750 a night in winter verses the nearly double rate of $1,429 a night in summer. Walk the beach and watch glacier-like ice form with the waves, warm up in the hot tub, and light a bonfire under starry winter skies framed by trees. Other notable options include the three-bedroom Harbor Time , new five-bedroom Darby Cottage with its massive showroom-worthy open kitchen, and new four-bedroom Lake Life that puts spectacular lake views right in your lap.

KOHLER, WISCONSIN

Distance from Chicago 149 miles

CNT Editors

Steph Koyfman

Shannon McMahon

One of the Kohler luxury Cabins

On a drive of just over two hours, cruise past Mars Cheese Castle in Kenosha (hit the brakes to load up on Wisconsin gold), and lakefront Milwaukee, on your way to Kohler. Popular in temperate months for its jaw-dropping golf courses, which regularly feature on the PGA Tour, Destination Kohler is a find in winter with fewer visitors, killer spa treatments at its Kohler Waters Spa, and invigorating outdoor adventures at its lesser-known River Wildlife preserve. Like Kohler’s golf courses, the 500-acre wilderness playground showcases the natural beauty of the landscape here. Try hikes and horseback rides through rolling trails, ice skating and curling at Winter Wonderland, guided trap shooting in a forest canyon, and brunch or hot toddies at River Wildlife Lodge, the preserve’s atmospheric log cabin outpost.

Options at the resort include classic hotel rooms at the 241-room American Club ( from $189 ), but four chic and splurge-worthy cabins (f rom $842 a night ) are the way to go, especially if you want privacy and space wrapped in some gorgeous nature. The two-bedroom Lake Cabin ( from $1009 a night )—one of two opened just last summer—positions you on a staggering bluff just above Lake Michigan. The beach is inaccessible from this rugged perch, but you won’t care with endless, ocean-like views from the back porch and firepit, and the sprawling evergreen forest at the front of the house that doubles as a wildlife crossing (watch for deer and wild turkeys). It’s all the more magical with a dusting of snow on the beach grass, a warm fire, and dinners inside your own beautiful kitchen—everything from tenderloin and ricotta gnocchi takeout from the new Taverne on Woodlake to whiskey pairings, curated Wisconsin cheese boards, and gourmet groceries delivered from Woodlake Market .

Distance from Chicago 164 miles

Downtown Galena

With rolling forested landscapes, an historic downtown on the Mississippi River, and the best (one of the only!) ski mountain in Illinois, Galena is as charming as ever in winter. Even the two-hour-and-45-minute drive sets the mood as flat highways turn to one-lane roads that climb gentle hills and weave through farmlands and woods, eventually dropping you into this once-thriving river port town. Stroll the downtown’s Main Street for a superb array of local shops and studios; new options include Galena Book & Paper , the Galena Spoon Company for handcrafted spoons and carving classes, and Scent Workshop , where you can learn French perfuming techniques. There are loads of restaurants and boozy options here, too; go for especially good take-home dining and cocktail kits from French-meets-German Fritz and Frites , Miss Kitty’s Grape Escape , and the drive-thru Galena Brewing Co . Downhill skiers won’t want to miss Chestnut Mountain Resort, just 15 minutes from the downtown, with 19 runs that race to a halt at the bank of the Mississippi River.

It’s a-okay to vape in the new guest-only “potting shed” outside the pretty five-bedroom Aldrich House , Illinois’ only cannabis-friendly bed and breakfast ( from $145 a night ). For something upscale and romantic, it’s hard to do better than the luxury six-suite Jail Hill Inn , set in a former jailhouse at the end of Main Street and serving a three-course breakfast ( from $345 a night ). Families settle in nicely at the stylish, condo-like Ulysses Suites ( from $214 a night ), while south of downtown on 6,800 acres of Galena Territory, Eagle Ridge Resort & Spa offers a robust nordic activities program and everything from simple hotel rooms to full homes ( from $99 a night ).

INDIANAPOLIS, IN

Distance from Chicago 185 miles

The Bottleworks Hotel in Indianapolis' Bottleworks District

Every worthwhile weekend getaway from Chicago isn’t a charming small town or lakeside retreat. For those who want some city culture that isn’t their own, Indy’s Bottlework’s District is calling. Stop in Merrillville for proper road trip junk food—fresh Indiana-made gummy bears—at Alabanese Confectionery Group on the three-hour drive south to Indy. Once there, head to the new 12-acre, mixed-use neighborhood that spans the north side of Mass Ave in downtown Indianapolis and brims with local indie shops in historic industrial buildings. Explore the mix of offerings at Circle City Industrial Complex , a 500,000 square-foot warehouse opened in the old Schwitzer car manufacturing facility, where you should check out newly opened SoChatti dairy-free chocolate tasting room and a class at Indy Fused Glass. Other new places worth a visit are Good Neighbor for fresh duds and the Living Room movie theater. For dinner, head out of the district for romantic outdoor dining in the new fireside greenhouse huts at Public Greens , a modern, community-driven restaurant that shares its profits to feed nearly 2,000 of Indy’s less fortunate youth every week.

Opened in December in what was formerly the world’s largest Coca Cola bottling plant, the 139-room Bottleworks Hotel ( from $249 a night ) is the stylish new anchor for the Bottleworks District. The industrial, art-deco-inspired hotel occupies the top two floors of the historic building, showing off a white terra-cotta exterior and brass-patterned doors. High-style rooms have velvet couches, loft ceilings, and terrazzo-tiled floors. Adjacent to the hotel, find more dining options at Garage Food Hall , Indy’s first food hall opened this month in the factory’s former garages, with nearly two dozen vendors serving everything from lobster rolls and poke to Pakistani-Indian fare and Brazilian steak.

BOYNE, MICHIGAN

Distance from Chicago 346 miles

A look down Boyne Mountain

Make your winter ski trip happen at Boyne Mountain Resort , one of the most exciting ski mountains within a reasonable drive of Chicago—five and a half hours, plus a one-hour time change. Rising up from the northern part of Michigan’s lower peninsula, the mountain offers 500 feet of vertical with 60 downhill trails for a range of skiers and riders, though the biggest perk of a visit here is the abundance of high-quality outdoor adventures that go beyond skiing. Rent a new sno-go ski bike and shred downhill runs, fat-tire bike on forest trails, zipline 50 feet in the air across the mountain, cross country ski or snowshoe on dedicated trails, ice skate or snow tube, and even dine outdoors in one of five igloos serving at Forty Acres Tavern. If you have a little extra time you can also tack on the 40-minute drive north to Boyne Highlands , the mountain’s sister resort, for even more challenging ski terrain plus the new “Enchanted Trail,” an illuminated two-mile trail for nighttime winter walks and snowshoeing. NOTE: Like other ski resorts around the country, both mountains are limiting capacity during the pandemic and booking lift tickets and gear rental in advance is recommended.

Spread out in one of the fully-equipped three- and four-bedroom Mountain Cabins that are part of the resort (f rom $607 per night ). Each is set in the woods with a hot tub on the deck, fully equipped for cooking your own meals, and offers ski-in/ski-out access. Some of the cozy one- and two-bedroom condos at the Village at Disciples Ridge also offer ski-in/ski-out access ( from $488 per night ). Pro tip: the best way to guarantee access to the slopes this season along with your accommodations is to book a “ Ski & Stay Package ,” which bundles lodging and lift together and lets you ski both resorts.

Recommended

By signing up you agree to our User Agreement (including the class action waiver and arbitration provisions ), our Privacy Policy & Cookie Statement and to receive marketing and account-related emails from Traveller. You can unsubscribe at any time. This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

9 Spectacular Must-Do Day Trips From Chicago (2024 Guide)

• Last Updated: February 4, 2024

Looking for a good day trip from the Windy City? Here are 9 amazing day trips from Chicago that include state parks, beaches, historic sites and more.

Chicago is a city of mouthwateringly good deep-dish pizza, pristine architecture, and an enriching atmosphere. Full of top-notch restaurants, eye-catching fashion, and upscale attractions, the Windy City is a place people travel from all over to visit.

A place of innovation, Chicago is constantly up to speed with new trends – or establishing the trends for everyone to catch onto.

Of course, as the birthplace of modern architecture, this is not a big surprise. Still, a visit here catches one’s eye with the fascinating designs and structures of the buildings within the third largest city in the United States. 

While visiting this trendy city, we recommend spending a day outside Chicago to see nearby top attractions like state parks full of hiking trails. There is so much to see outside the town center of Chicago, so why not add a day trip or two to your Chicago itinerary ?

The best way to get around is to rent a car and explore on your own! We recommend Rental Cars , which has the largest range of vehicles for the best value on the market.

Table of Contents

What Is There To See And Do?

Getting there and away, best time of year to visit, the 9 best day trips from chicago.

It’s time to spread your wings and leave the city on an incredible day trip. Take your pick from our curated selection of the 9 best day trips from Chicago. From living in luxury in Lake Geneva to exploring the rich history and architecture of Oak Park, get ready to have the time of your life.

Find more of the best things to do in Chicago here !

1. Starved Rock State Park

• Distance from Chicago: 91 miles/146 km
• How Long it Takes: 1½ Hours

Settled along the Illinois River, Starved Rock State Park is an oasis teeming with seasonal waterfalls, towering sandstone canyons, thriving wildlife, and scenic hiking trails.

However, the most well-known landmark at the park is the cliff the park is named after – Starved Rock. This imposing sandstone cliff is a natural landmark that holds history. 

Archaeological excavations have been run at Starved Rock for further research to verify information shared throughout history. In 1683, the French used Starved Rock to establish a fort called Fort St. Louis. It was later abandoned in 1691. 

The sandstone cliffs were named “Starved Rock” by Native Americans in 1770 after what is estimated to be about 2,000 Native Americans died atop the cliffs. This was after the Potawatomi Indians attacked the Peoria Indians.

As a result, the Peoria Indians were trapped on the rock and suffered starvation. 

Today, Starved Rock State Park has become a favored spot to sink into nature’s beauty. People come from all over to see Starved Rock and other popular landmarks, including the St. Louis Canyon Falls.

The St. Louis Canyon Falls towers an impressive 80 feet, one of the highest waterfalls in Illinois. In summer and spring, visiting these falls is one of the top activities to do at the park. You can also go kayaking , canoeing, or try other water sports.

Top attractions in the park include:

• St. Louis Canyon Falls
• Aurora Canyon
• Illinois Canyon
• Starved Rock State Park Lodge 

Popular hiking trails:

• St. Louis Canyon Trail
• River Trail
• Bluff Trail
• French Canyon Trail

There are two popular methods of getting to Starved Rock State Park from Chicago without a car. The first is taking the train from Chicago Union Station to Mendota Amtrak Station. The second would be to take a taxi, which can be much more expensive but is a quicker route.

We recommend visiting from April to September as it’s ideal weather for outdoor activities. If you’re an avid birdwatcher, then the best time of year to visit Starved Rock State Park to see the eagles is in January and February. 

The spring is the best time to see the waterfalls as they are seasonal and fed by heavy rains often experienced during the spring.

The summer is the most popular time to visit Starved Rock State Park. Unfortunately, this is when the park can get overcrowded, resulting in the park cutting off entry for visitors, as many people come to kayak and raft on the river. 

2. Lake Geneva

• Distance from Chicago: 83 miles/134 km
• How Long it Takes: 1 Hour 45 Minutes

A resort city, Lake Geneva, was named “Newport of the West” after the American Civil War. The year-round resort city was where rich Chicago residents constructed their summer homes. Some famous names that visited the area include General Sherman and Mary Todd Lincoln. 

This area has a rich history, where ancient Oneota Tribes of the lost Hopewell Culture Indians once thrived. Archaeological evidence suggests that the Oneota Tribes had an advanced civilization here in 1,000 BC.   

Today, Lake Geneva is one of the best weekend getaways from Chicago. A day trip or weekend trip here is worth taking because of its natural beauty, impressive architecture, and luxurious resorts.

Take your pick of boating on the lake, hot air ballooning over the resort city, joining a history tour, or sinking into luxury with a spa day at The Abbey Resort.

Examples of popular things to see include:

• Riviera Beach
• Big Foot Beach State Park 
• Lake Geneva Shore Path
• Royal Oak Farm 
• Safari Lake Geneva

There are no trains directly connecting Chicago to Lake Geneva. Another option would be to take the train from Chicago Union Station to Fox Lake. From there, snag a taxi to this Wisconsin resort city. 

To catch some sun outdoors by the lake, the best time to visit Lake Geneva is in the summer. This is the optimal time for weekend getaways or day trips from Chicago. The days get hot, so wear sunscreen and bring plenty of water to stay hydrated.

Have 3 days to spare in Chicago? Check out our ultimate 3-day itinerary ! 

3. Indiana Dunes National Park

• Distance from Chicago: 39 miles/62 km
• How Long it Takes: 1 Hour

One of the best day trips from Chicago, Indiana Dunes National Park is thriving with natural wonders with over 50 miles of scenic trails to observe these eye-catching features. A road trip through here is sure to be a beautiful one!

The park has one of the most biologically diverse habitats in the United States, including wetlands, shorelines, prairies, and sand dunes. This includes the 15 miles of Indiana Dunes National Park beaches stretching down Lake Michigan’s southern tip. 

Though the beach is one of the top things to do when visiting Indiana Dunes National Park, the park is also notorious for its rich history.

The Bailly Homestead, a National Historic Landmark, was the home of one of the first settlers in the area, Joseph Bailly de Messein. This fur trader’s trading post acted as an in-between for travelers from Detroit to Chicago. 

Top attractions in the park:

• Chellberg Farm
• Bailly Homestead
• Kemil & Dunbar Beaches
• Paul H. Douglas Trail 
• Great Marsh Trail
• Cowles Bog Trail
• Dunes Succession Trail (Diana of the Dunes Dare)

The best way to get to Indiana Dunes National Park is by renting a car. Unfortunately, there are no methods of transport that take you directly to the park. You can take a taxi, but it will be quite expensive!

Summer is the best time of year to visit Indiana Dunes National Park. This is when the beaches are open and prime for sunbathing and swimming. Other activities like fishing and hiking to see the sand dunes are also great at this time. 

4. Silver Beach County Park

• Distance from Chicago: 98 miles/157 km 
• How Long it Takes: 1 Hour 45 Minutes 

Bordering four states, Lake Michigan seeps into Illinois, Indiana, Michigan, and Wisconsin. Though Lake Michigan is technically within access of Chicago, with popular attractions like the Navy Pier and Millenium Park, one of the top day trips from Chicago is Silver Beach County Park.

Located at the mouth of the St. Joseph River on Lake Michigan’s southern shore, Silver Beach County Park has lots of picturesque viewpoints.

The long, clean stretch of beach has become a top tourist destination with upgraded renovations made to the park to promote accessibility and convenience. 

Access to Silver Beach County Park is free, though parking can be tricky depending on how busy it is. The barrier-free walkway gives easy access to the South Pier, Dunes Pavilion, concession stand, Shadowland Pavilion, and restrooms.

Using the park’s sidewalks along the beach, you can reach the Silver Beach Center, find the Whirlpool Compass Fountain, and take a refreshing stroll to downtown St. Joseph.

Cool things to see in the area:

• Silver Beach Carousel
• Krasl Art Center
• Harbor Shores Golf Club
• Whirlpool Compass Fountain

There are several ways to get to Silver Beach County Park from Chicago without a car. The first is a train ride from the Chicago Union Station to St. Joseph-Benton Harbor, Michigan.

The second is a bus ride from the Chicago Bus Station to Benton Harbor and a taxi to Silver Beach County Park. The third would be getting a taxi or renting a car to reach Silver Beach County Park. 

Silver Beach County Park is open daily from dusk to dawn. For swimming, the best time of year to visit is usually anywhere from July to September. Lifeguards are on duty at the park from June to August. 

Exploring more of the Midwest? Check out our list of the best things to do in Minneapolis, Minnesota !

5. Anderson Japanese Gardens

• Distance from Chicago: 85 miles/137 km

One of the highest-quality Japanese gardens in the United States, the Anderson Japanese Gardens is among the most rewarding Chicago day trips.

The authentic Japanese garden inspires by its refined outdoor setting that has been maintained and designed with the highest standards.

The Anderson Japanese Gardens were designed by Hoichi Kurisu, who established many other Japanese gardens, including the one at the Samaritan Lebanon Community Hospital that won the Healthcare Environment Award in 2006 for Landscape Design. 

Exuding eloquence and grace, this location soothes the soul as guests stroll through the thriving landscapes.

Yoga sessions are taught within the gardens in the Hatha Yoga tradition amongst the refreshing air of the gardens. There are beginner, intermediate, and advanced classes for Tai Chi led at the gardens to encourage relaxation and mental focus. 

Fun things to do here include:

• Amanda Stivers yoga
• Sound & gong bath
• Awareness walks

Other fun things to do in the area include:

• Rockford Art Museum
• Laurent House
• Prairie Street Brewing Company
• Nicholas Conservatory & Gardens
• Burpee Museum of Natural History
• Discovery Center Museum

Take the bus from the Chicago Union Station to Rockford Amtrak Station. From there, hitch a ride on a taxi.

Another option is to take the subway Jackson-Blue to O’hare in Bensenville. Once you reach the station, hitch a bus ride from the Chicago – O’hare Airport to the Rockford Bus Terminal. Then, grab a taxi to reach the gardens.

Taking a car is the second best option for a more cost-effective option, but it is more convenient than taking the bus and taxi to reach Anderson Japanese Gardens.

The best time to witness the stunning transition of the leaves as they turn color at Anderson Japanese Gardens is in Fall, from September to October. However, summer is the peak season, so if you want to avoid the crowds stick to visiting in the spring or fall. 

6. Oak Park

• Distance from Chicago: 10 miles/15 km
• How Long it Takes: 20 Minutes

Within a short distance from Chicago, Oak Park is a historically rich village place to visit. It is also considered one of the best places to live in Illinois, intertwining suburban and urban living in one favorable family-friendly location. 

There are plenty of activities in the area, with family-friendly attractions like the Brookfield Zoo and the Galloping Ghost Arcade. The arcade is the largest video arcade in the United States. Oak Park is notorious for its trendy restaurants like Maya Del Sol or Hemmingway’s Bistro. 

If you’re a history buff or appreciate architecture, you’ll love this beautiful spot. Renowned architect Frank Lloyd Wright showcased his talent here for the first 20 years of his career.

Walking tours take visitors past significant historical and architectural sites such as Wright’s home, the Frank Lloyd Wright Home and Studio. 

There is also the home of famed author Ernest Hemingway, who grew up in Oak Park. The Ernest Hemingway Foundation restored Hemingway’s home, and now tours of the author’s birthplace are given. Join a guided architecture tour to learn all about the history and creativity of the area’s top attractions!

Top sights here include:

• Frank Lloyd Wright Home and Studio
• Ernest Hemingway Birthplace Museum
• Brookfield Zoo 
• Oak Park Conservatory

There are lots of convenient ways to get from Chicago to this charming village. The train at Chicago OTC and the subway both head straight to Oak Park at inexpensive prices. The fastest way to get there would be a taxi, though this will run a little more costly than the subway or train. 

The Line 20 bus also comes here at an affordable price, though it will take longer to reach your destination as stops are included. 

Oak Park’s busiest month is from May to July. However, we recommend visiting anywhere from August to October if you want to avoid the crowds and high prices for these tourist-heavy months. 

Read next: The 21 Best Things To Do In St Louis, Missouri

7. Holland, Michigan

• Distance from Chicago: 152 miles/245 km
• How Long it Takes: 2½ Hours

Notorious for its award-winning breweries, Holland, Michigan, is only a few hours from Chicago and worth the trip. 

Holland’s natural beauty and charm are one for the books, with its lush nature, flower-speckled fields, and waterfront views.

The city is home to numerous parks to choose from for a picturesque stroll through nature with outstanding vistas. Holland’s downtown is thriving with locally-owned businesses to shop at.

The historic area was named one of “America’s Prettiest Towns” by Forbes magazine, with its cobblestoned sidewalks, live performances, and award-winning eateries and breweries to choose from. 

The Windmill Island Gardens is one of the top attractions in Holland. The gardens feature a 251-year-old windmill called De Zwaan. It is the only authentic Dutch windmill working in the nation.

Holland State Park is another largely popular attraction. The park showcases its iconic “Big Red” lighthouse for breathtaking sunset scenery and long stretches of beach on Lake Macatawa and Lake Michigan.

Many travel to the park to go camping, fishing, paddleboarding, sunbathing, and more for one of the best weekend trips from Chicago.

• Windmill Island Gardens
• Holland State Park
• Holland State Park – Macatawa Campground
• Big Lake Brewing
• Saugatuck Dunes State Park

For those without a car, there is a direct connection by train from the Chicago Union Station to the Holland Amtrak Station. However, if you have a car or can rent one, that is the only other option to get back and forth to avoid ridiculous fees for a taxi. 

We recommend visiting Holland in spring when the flowers bloom to see the tulips that the area is known for. They usually bloom around late April and continue to bloom to mid-May.

Visiting Holland in the summer is extremely popular, so if you don’t mind crowds and want to catch some sun, take a trip to the city to soak in the sun and picturesque views. 

8. Peoria, Illinois

• Distance from Chicago: 173 miles/267 km
• How Long it Takes: 3 Hours

Nestled along the Illinois River, Peoria is a bustling shipping center and agricultural production zone. Presenting a suburban feel, the city has family-friendly attractions to savor. It was once known as the Whiskey Capital, with 40% of alcohol produced in the United States coming from Peoria in 1890. 

On the city’s historic Distillery Row along the Illinois River, visitors can taste Peoria’s specialized whiskey distilleries that have maintained the city’s legacy.

There is much to see and do in Peoria. Designed by Pritzker Prize-winning architects John Burgee and Philip Johnson, the Peoria Civic Center is a hotspot attraction in downtown Peoria. The center showcases an exhibit hall, an arena, and a theater that hosts live entertainment for comedians, Broadway shows, concerts, and more.

The Luthy Botanical Garden is a refreshing stroll through themed gardens, including a children’s, Japanese, rose, and herb garden. It was also the first botanical garden in the state.

For a fun new experience, hitch a ride on this guided architecture cruise to experience the iconic architecture along the Chicago River. 

Top things to do include:

• Peoria Civic Center
• Peoria Riverfront Museum
• Louisville Slugger Sports Complex
• Forest Park Nature Center
• Luthy Botanical Garden

The cheapest method of getting to and from Peoria from Chicago is by driving. Another method of taking the train from the Chicago Union Station to Peoria Amtrak Station. This route will take longer than the alternative of going by car. 

The most popular time to visit Peoria is in the summer. However, if you’re looking for cooler weather, we recommend visiting the city in September to early October when the weather is getting cooler.

Read next: 23 Best Things To Do In Kansas City, Missouri

9. Michigan City

• Distance from Chicago: : 60 miles/96 km
• How Long it Takes: 1 Hour 15 Minutes

The source of Michigan City’s name is initially confusing for many. The city was not named after the state of its namesake but Lake Michigan that it is near. Michigan City is a favored tourist spot thanks to its convenient location near top attractions such as Indiana Dunes National Park and Lake Michigan. 

The city has a rich history with a small-town charm, and history buffs will be pleased to find the city flooded with attractions.

The historic city preserves its oldest structure, a lighthouse established in 1858, at the Old Lighthouse Museum. It was the home of the creator of Wikipedia, Howard G. “Ward” Cunningham, who grew up in the city.

The Barker Mansion is an English manor built in 1857, preserving period furnishings from the Gilded Age. It is part of the National Register of Historic Places and is open for tours.

Michigan City is a rewarding day trip from Chicago. Other than its historical attractions, there are nature-based activities such as Friendship Botanic Gardens and Indiana Dunes National Park. Go for a relaxing evening or tour the vineyards at Shady Creek Winery. Or test your luck at the Blue Chip Casino Hotel Spa.

Top attractions include:

• Washington Park Zoo
• Friendship Botanic Gardens
• Shady Creek Winery
• Blue Chip Casino Hotel Spa
• Michigan City Lighthouse and Pier

In Chicago, there are direct routes to take on the buses and trains that head to Michigan City from Chicago. Other than that, the only other inexpensive way to reach Michigan City is by driving. 

Ideally, summer or early fall in September is the best time to visit Michigan City to savor outdoor activities while in town.

Unfortunately, the winter months are frigid, from November to February. Therefore, we recommend not visiting during these months if you plan on spending time outdoors at the parks or gardens. 

DISCLAIMER: Some of the links in this article are affiliate links, which means if you book accommodation, tours or buy a product, we will receive a small commission at no extra cost to you. These commissions help us keep creating more free travel content to help people plan their holidays and adventures. We only recommend the best accommodations, tours and products that ourselves or our fantastic editorial team have personally experienced, and regularly review these. Thanks for your support, kind friend!

Alesha and Jarryd

Hi, We’re Alesha and Jarryd!

We’ve been traveling the world together since 2008, searching for the planet’s best destinations and adventures.

Love Travel?

Sign up for our free weekly newsletter for the best travel tips, ideas and deals!

We respect your privacy. Unsubscribe at any time.

READ MORE...

The Ultimate 3 Days in New York City Itinerary (2024 Update)

25 Best Things To Do In Santa Fe, New Mexico (2024 Guide)

The 21 Best Things To Do In Richmond, Virginia (2024 Guide)

Related Posts

21 best things to do in las vegas, nevada (2024 guide), arkansas road trip itinerary – the perfect 7-day route, 25 of the best things to do in kona hawaii (2024 guide), 21 best things to do in los angeles, california (2024 guide), leave a comment cancel reply.

Save my name, email, and website in this browser for the next time I comment.

• North Dakota
• South Dakota
• Exciting Cities
• Food And Drink
• Outdoor Adventures
• Where To Stay
• Skip to right header navigation
• Skip to main content
• Skip to primary sidebar

Learn how to easily plan your dream trip to the Midwest!

15 Best Day Trips From Chicago Worth The Effort

August 13, 2022 by //  by  Midwest Explored 1 Comment

Are you looking for the best day trips from Chicago that are actually worth the effort? Then this list is for you!

Maybe you want a break from the city, or maybe you just want to explore a new city.

Planning your trip to Chicago last minute?

Make sure to book ahead. Hotels and tours often sell out the closer you get to your trip. Here are our top pics for Chicago!

Top Experiences And Tours In Chicago:

• Chicago River Architecture Cruise (Skip the Ticket Office!)
• Willis TowerSkydeck & The Ledge Ticket (Elevator express entry!)
• Navy Pier Centennial Wheel Ticket (Panoramic views of Chicago!)
• Big Bus Hop on Hop Off Sightseeing Tours (24, 48, or 72-hour options available.)

Hop Hotels In Chicago:

• Eurostars Magnificent Mile (In the heart of Chicago!)
• The Peninsula Chicago (Near museums)
• Club Quarter Hotels Wacker (Overlooking the Chicago River!)
• Hotel Blake (Close to Millennium Park.)

No matter your interests you’ll find a great day trip option on this list.

I’ve found some of the most unique, fun, and adventurous day trips to make from Chicago.

There are beautiful state parks, metropolitan cities, unique and charming small towns, and so much more.

So, lets take a look at the 15 Best Day Trips from Chicago Worth The Effort!

Cedarburg, Wisconsin

In just under 2 hours, you can find yourself in the charming small town in Wisconsin called Cedarburg.

Cedarburg is an excellent day trip from Chicago for those looking for small-town charm, but with plenty of activities.

Because Cedarburg is know for its small town atmosphere, you’ll find some really unique shops and resturants.

There is a Candy Kitchen, an Amish Craftsmen Guild, stores full of items made by local artisans, and even a shop where you can search for unique gemstones.

Cedarburg also has a wide variety of unique museums.

There is a local art museum, a local history museum, a woolen mill and textile museum, and even a museum depicting early life in Cedarburg.

No matter your interests, Cedarburg is guaranteed to have something fun for you to do, and you’ll find it was worth the drive.

Rockford, Illinois

If you drive for about an hour and a half West of Chicago, you’ll find yourself in Rockford Illinois.

The best way to describe Rockford is to call it a big-little city. It’s the fourth largest city in Illinois, but still feels welcoming in a small-town sort of way.

Rockford is also bursting with things to do.

Music lovers will enjoy checking out one of the many spots home town band Cheap Trick helped make famous.

If museums are more your thing, don’t worry, Rockford has those too. Stop by the Burpee Museum of Natural History or the Discovery Center Museum.

If none of that sounds interesting, then maybe you’ll like the Anderson Japanese Garden. It is consistently rated as one of the best Japanese Gardens in North America.

There is so much to do that you may want to turn your day trip into a Midwest weekend getaway . With the endless list of activities in Rockford, it absolutely makes it worth the hour and a half drive from Chicago.

Grand Rapids, Michigan

Grand Rapids Michigan is one of the perfect day trips from Chicago for lovers of art, food, and beer.

In fact, Grand Rapids is known as Beer City USA.

For those who want to take full advantage of all Beer City USA has to offer, you’ll want to download the Brewsader App.

The App gives you a full map of all the breweries in Grand Rapids, and after you check in at 8 of them, you’ll earn a fun Brewsader shirt to commemorate your trip.

If beer isn’t your thing, not to worry.

There are still some absolutely amazing and unique restaurants in Grand Rapids you can check out. Or you can stop into one of the cities popular art galleries.

There really are so many cool things to do in Grand Rapids .

Oak Park, Illinois Is One Of The Best Day Trips From Chicago

Oak Park Illinois is the shortest distance you’ll have to travel for a day trip on this list as it’s just under 20 minutes outside of Chicago.

Despite that, many people in Chicago, or even visiting Chicago, don’t think to explore Oak Park.

Admirers of Frank Lloyd Wright, one of America’s most prominent architects will know Oak Park though.

Wright called Oak Park home, and left his mark on many of the cities most popular homes and buildings.

Oak Park was also home to another famous architect, George W. Maher, who also designed many of the cities most prominent homes and buildings.

Ernest Hemingway was also born in Oak Park, and you can visit his childhood home that has now been turned into a Hemingway Museum.

Book Tickets Here: Ernest Hemingway Boyhood Tour

Because of Oak Park’s proximity to Chicago, many gangsters in the early 20th century called the area home, and you can now take a Gangster tour.

Oak Park is a tremendously unique option for a day trip from Chicago and you don’t even have to travel far!

Michigan City, Indiana

Michigan City Indiana is about an hour away from Chicago, and you’ll spend the whole trip driving along Lake Michigan.

So it’s no surprise that Michigan City also has its fair share of lighthouse history.

In Michigan City you’ll be able to explore the Old Lighthouse Museum and even take a tour of the Michigan City Lighthouse and Pier.

Stroll along the beach or maybe head over to the Washington Park Zoo, which is full of more interesting architecture, and of course animals.

Travelers also enjoy touring the Barker Mansion and sipping on local wines at some of the best wineries in Indiana

Monroe, Wisconsin

Monroe Wisconsin is the Swiss Cheese Capital of the USA, and just over 2 hours away from Chicago.

Cheese lovers will delight in the many, many, cheese related activities that abound in Monroe.

Monroe is a cute small town that takes cheese very seriously, and for good reason. The city has thrived for over 100 years because of it’s cheese industry.

You can pair some locally made cheeses with local beers or just explore the numerous cheese shops.

Or watch a movie at the local drive-in theater while munching on cheese curds.

The small town even holds a yearly Cheese Days Festival where you can sample all of the local cheeses while sipping a cold local beer.

Monroe is perfect for your next day trip from Chicago the next time you’ve got a serious craving for all things cheese.

This cool town is one of the best places to visit in Wisconsin.

Kankakee, Illinois

Kankakee Illinois is a cute town in Illinois just over an hour south of Chicago.

It’s full of small town charm but it still has a lot of interesting things to do, making it perfect if you’re looking to escape the city for a day.

One of visitors favorite things to do in Kankakee is taking a tour of the B. Harley Bradley House, a famous house designed by Frank Lloyd Wright.

Kankakee is also amazing for those looking for a little outdoor adventure.

The entire Kankakee County and parts of the city of Kankakee are bursting with outdoor activities.

You can enjoy some of the best hiking in Illinois , along with canoeing, kayaking, and even scuba diving in the Haigh Quarry.

Kankakee is one of the best day trips from Chicago Illinois if you’re looking for fresh air, beautiful views of nature, and plenty of small-town charm.

New Glarus, Wisconsin

America’s Little Switzerland is in New Glarus Wisconsin, just 2 and half hours outside of Chicago.

New Glarus is a small town that loves beer, cheese, and festivals. In the warmer months, they may have 3-4 festivals a month.

Typical New Glarus festivals include Polkafest, The Beer, Bacon, & Cheese Festival, The Heidi Folk Festival, Blues Brews & Food Trucks Festival, Maxwell Street Days, and so many more.

New Glarus is also known for having a selection of brews that you can only buy in Wisconsin, and some of them you can only buy in New Glarus.

If you are a beer connoisseur, you’ll love checking out one of the local beer gardens. And if you decide to stay longer here are some epic Wisconsin Airbnbs to look into.

Foodies will love checking out one of the many restaurants that serves up Swiss and Swiss inspired fare.

New Glarus is a cute romantic getaway in Wisconsin!

Holland, Michigan

Holland Michigan is a little over 2 hours away from Chicago and is one of the best day trips from Chicago that is definitely worth it.

Named after the home country of it’s original settlers, Holland is bursting with Dutch charm.

In the Spring it’s host to the Tulip Time Festival where you will get to see a riot of colorful tulips with a windmill that is straight from Holland.

Even if you can’t make it to the Tulip Time Festival, you’ll love exploring this cozy small town.

There are plenty of unique shops, restaurants, breweries, and unique Dutch gardens.

Holland is also home to one of the coolest lighthouses in Michigan , The Big Red Lighthouse.

Visitors love to view the iconic lighthouse standing proudly on it’s pier, with the bright red façade making a striking contrast against Lake Michigan.

Holland is a small town in Michigan full of charm that is definitely worth the effort to visit, any time of year.

Milwaukee, Wisconsin

If you are looking to explore a city, but you want a break from Chicago, then I suggest driving the hour and half to Wisconsin’s largest city, Milwaukee.

Because Milwaukee is Wisconsin’s biggest city, it is full of unique things to do making it one of the best day trips from Chicago!

And there are so many things to do in Milwaukee!

If you’re on a budget, take a stroll down the streets and admire the many murals on the sides of buildings. Or go window shopping and one of the many boutique stores.

You can also check out a play or musical, go on a boat tour of Milwaukee, or explore one of the amazing restaurants in Milwaukee.

If you’re a sports fan, you may want to check out one of Milwaukee’s home teams. Afterwards, you can talk about the game at one of the cities awesome bars or resturants.

Milwaukee is an amazing city that often gets overlooked, but you won’t regret making the trip out there.

Oglesby, Illinois

In just under two hours you can be in beautiful Oglesby Illinois.

Oglesby is perfect for day trippers looking for a break from the city as it is home to two beautiful State Parks.

If you’re looking for some outdoor adventure and clear air, then you’ll find that this is one day trip that is worth the effort.

At Starved Rock State Park you’ll find trails that lead you along the Illinois River and into steep sandstone canyons.

It is Illinois’ most popular State Park and for good reason. It’s accessible for all skill levels and you get to experience some beautiful views.

The other state park near Oglesby is Matthiessen State Park. The entrance for this park is just a few miles South of Starved Rock State Park.

Matthiessen State Park has similar views, but it is often far less crowded.

It is a great choice to experience fall in Illinois.

You’ll still be able to hike beautiful trails, see gorgeous Illinois waterfalls, and enjoy nature, but you’ll be far less crowded.

If you have plenty of time on one of your day trips from Chicago Illinois, you should definitely check out both state parks.

Lake Geneva, Wisconsin

Lake Geneva is a Wisconsin town about an hour and a half outside of Chicago.

It has a history of being the go-to spot for Chicago’s wealthy families during the summer.

Lake Geneva is a beautiful small town that thrives because of the large Lake Geneva, and it’s a budget-friendly day trip option.

There are so many things to do in Lake Geneva all year long that include lake activities.

But you’ll also find a charming town full of unique boutiques, restaurants, and even outdoor activities like hiking and snow sports in the winter.

In early February the town holds a Winter Fest which features the only snow sculpting championship in the United States.

Visitors get to experience massive snow sculptures, food from local restaurants, and so much more – and it’s free to attend!

In the summer, enjoy boating, swimming, and kayaking on Lake Geneva before having a meal at one of the amazing local restaurants in Lake Geneva .

No matter what time of year you visit, Lake Geneva is a Chicago day trip that is worth the effort.

Highwood, Illinois

Highwood Illinois is another small town that goes big when it comes to festivals.

Just 35 minutes North of Chicago, this charming small town is the perfect day trip from Chicago Illinois for festival lovers

There’s almost a festival every month, and they all have different themes.

For foodies, there is a Taco Festival, a Bloody Mary Festival, and a Garlic Festival.

There are also smaller music festivals, fun runs, and a Pride Festival.

One of Highwood’s most iconic festivals though is probably The Great Highwood Pumpkin Festival every October.

It is one of the coolest things to do in Illinois .

The Festival benefits the Make-A-Wish Foundation and attendees get to check out rows and rows of carved pumpkins.

Attendess of Pumpkin Fest can even bring their own pumpkins and carve them before adding them to the walls of carved pumpkins.

Highwood is a truly unique town, full of really cool festivals that are sure to make the trip out there worth the effort, no matter what time of year you go.

Indiana Dunes National Park, Indiana Is One Of The Best Day Trips From Chicago

Just under an hour outside of Chicago, the Indiana Dunes National Park is one of the coolest national parks in the Midwest.

The Indiana Dunes National Park is on 15 miles of beach on Lake Michigan’s South shore.

It is a nature lover’s dream with over 15,000 acres of preserved land full of unique hiking trails, wetlands, prairies, woodlands, and of course beaches.

From Memorial Day to Labor Day, there is a $6 entrance fee to enter the park. During the ‘off season’ though, it’s free to enter.

The Indiana Dunes is full of fun things to do, and you could spend days exploring the park making it a fun weekend getaway in Indiana!

It’s a beautiful spot, and it is definitely one of the day trips from Chicago that is worth the effort.

Madison, Wisconsin Is One Of The Cool Day Trips From Chicago

In just over two hours you can find yourself in Madison Wisconsin.

If you’re looking for a fun Chicago day trip in the summer, Madison is perfect for you.

With five lakes, spanning over 15,000 acres, in summertime there are so many things to do in Madison.

There are water sports, festivals, water front dining, and so much more.

But Madison isn’t just a fun place to visit in the summer.

You’re sure to find fun no matter what time of year you go.

There are dinner theaters, breweries, delicious restaurants, and unique boutiques. Put treating yourself at some of the restaurants in Madison on your list!

You’ll find that Madison Wisconsin is one of the most entertaining day trips from Chicago that is definitely worth the effort.

Packing List For Daytrips From Chicago

Here are some  tips on how to pack lightly

A  concealed travel pouch  may be one of the most important items you bring along when on one of your Chicago day trips! 

It is  always   important  to protect your personal information. Identity thieves are everywhere.

This  unisex RFID blocking concealed travel pouch is  lightweight and comes in several colors. It has lots of organization to give you peace of mind.

You can place it under your clothes next to your body to carry your ID safely.

If you have a pouch already that does not come with the RFID protection, as I do, these  RFID  sleeves  are the perfect solution.

This configuration comes with enough credit card sleeves that the entire family would be protected. They are slim too, so they will easily fit into your pouch or wallet. 

If you are planning on taking a lot of pictures with your phone you will definitely want to consider an  external charging battery .

This  Anker high-speed phone charging battery  is  the exact one  I carry with me on all of my trips.

It can be used on a variety of phones, not just an iPhone like I have. And wow is it fast!

I like that it holds its charging capabilities for several uses so I do not have to worry about it while out and about, and if I forget to recharge it at night, it will still be good to go the next day.

My daughter gifted me with this  FugeTek selfie stick and tripod   setup for my birthday. I absolutely love it!

It is made of lightweight aluminum and so easy to use.

It has Bluetooth connectivity and is a breeze to use for taking selfies with all those nature shots while on your Chicago day trips..

Hydration is so important when hiking. You want to remain hydrated throughout your hikes to support your immune system which in turn will be stronger to fight off any germs you will encounter during your travels. 

You will want to bring your own  refillable water bottle  with you. 

I never leave home on a trip without my  Bobble filtration bottle .  The 18.5-ounce size is perfect for hiking and it fits nicely in the pocket of a backpack.

When filled with water, it is not too heavy to carry. And the charcoal filter ensures fresh clean water whenever you fill the Bobble.

Perhaps you are traveling a long distance to Chicago Illinois and packing space is a premium in your suitcase, or in your car.

Then this  set of collapsible silicone foldable water bottles  would work well for you. Would not take up much space at all. 

You will want a  backpack or daypack  with you to store snacks, your water bottle, phone, extra clothes, etc.. when on one of your day trips from Chicago Illinois. No matter the time of day or evening.

This   foldable water-resistant backpack   would be great

It is very affordable and is available in many color options for you to choose from. The fact that it folds down into a zippered pouch will make it easy to pack!

I hope you enjoyed this list of the 15 Best Day Trips From Chicago Worth the Effort! There are so many great big cities and little towns outside of Chicago just waiting to be explored.

If you are spending a weekend in Chicago , one of these trips from Chicago would def be fun!

If you take a trip to one of these awesome places, I’d love to hear about it in the comments!

Reader Interactions

[…] Starved Rock State Park is about 2 hours west of Chicago. […]

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

Save my name, email, and website in this browser for the next time I comment.

• Destinations

25 Best Day Trips from Chicago

Last Updated By VI on April 18, 2024 in Things to Do in Illinois & Places to Visit

Milwaukee (1 hour 35 minutes)

Holland, michigan (2 hours 30 minutes), kettle moraine state forest (2 hours 40 minutes), lake geneva (1 hour 40 minutes).

• Complete List & Map

Also nicknamed the “City of Festivals”, Milwaukee is home to over two dozen celebrations, including Summerfest, the world’s biggest music fest. Seventy-five golf courses, 25 theaters, and 150 parks round out this day-trip getaway.

Late November brings the Dutch Winterfest and its Parade of Lights.

N1765 Highway G, Campbellsport, WI, Phone: 262-626-2116

This year-round getaway offers an eclectic mix of shops, restaurants, nightlife, outdoor activities, and points of interest.

Naperville (40 minutes)

Visitors can also visit the popular Centennial Beach and Grill, a sandy beach waterpark and restaurant. More ideas: Beaches in Illinois

Village of Oak Park (15 minutes)

Visitors may also like the Oak Park Conservatory, and Brookfield Zoo. There are numerous independent shopping boutiques, a robust culinary scene, and a Saturday farmers’ market.

Six Flags Great America (1 hour)

1 Great America Parkway, Gurnee, IL, Phone: 847-249-1776

North Utica (1 hour 45 minutes)

Four nearby state parks provide outdoor recreational opportunities.

Chicago Botanic Garden (35 minutes)

1000 Lake Cook Road, Glencoe, IL, Phone: 847-835-5447

Indiana Dunes National Lakeshore (1 hour)

More ideas: Day Trips From Chicago By Train

Old State Capitol State Historic Site (3 hours)

Old State Capitol Plaza, 6th and Adams Streets, Springfield, IL, Phone: 217-785-7960

Apple River Canyon State Park (2 hours 30 minutes)

8763 E. Canyon Road, Apple River, IL, Phone: 815-745-3302

Starved Rock State Park (1 hour 35 min)

2668 East 873 Road, Oglesby, IL, Phone: 815-667-4211

Brookfield Zoo (25 minutes)

8400 31st Street, Brookfield, IL, Phone: 708-668-8000

Abraham Lincoln Presidential Library and Museum (3 hours)

112 N. Sixth Street, Springfield, IL, Phone: 217-557-6250

Anderson Japanese Gardens (1 hour 40 minutes)

318 Spring Creek Road, Rockford, IL, Phone: 815-229-9390

The Morton Arboretum (35 minutes)

4100 Illinois Route 35, Lisle, IL, Phone: 630-968-0074

Cantigny Park (40 minutes)

1s151 Winfield Road, Wheaton, IL, Phone: 630-668-5161

Frank Lloyd Wright Home and Studio (20 minutes)

209 S. LaSalle Street, Suite 118, Chicago, IL, Phone: 312-994-4000

Huron-Manistee National Forests (4 hours)

1755 S. Mitchell Street, Cadillac, MI, 49601, Phone: 231-775-2421

Nicholas Conservatory & Gardens (2 hours)

1354 N 2nd Street, Rockford, IL, Phone: 815-987-8858

Oglesby (1 hour 40 minutes)

The town hosts a Harvest Fest in mid-October with family-fun activities, and a Santa’s Holiday Open House in mid-December, featuring carriage rides and other holiday activities.

White River State Park (3 hours)

801 W Washington Street, Indianapolis, IN, Phone: 800-665-9056

Peoria (2 hours 40 minutes)

Visitors will revel in the breweries, restaurants, museums, festivals, historic riverboat rides, and weekend farmers’ market.--->

• 1. Milwaukee (1 hour 35 minutes)
• 2. Holland, Michigan (2 hours 30 minutes)
• 3. Kettle Moraine State Forest (2 hours 40 minutes)
• 4. Lake Geneva (1 hour 40 minutes)
• 5. Naperville (40 minutes)
• 6. Village of Oak Park (15 minutes)
• 7. Six Flags Great America (1 hour)
• 8. North Utica (1 hour 45 minutes)
• 9. Chicago Botanic Garden (35 minutes)
• 10. Indiana Dunes National Lakeshore (1 hour)
• 11. Old State Capitol State Historic Site (3 hours)
• 12. Apple River Canyon State Park (2 hours 30 minutes)
• 13. Starved Rock State Park (1 hour 35 min)
• 14. Brookfield Zoo (25 minutes)
• 15. Abraham Lincoln Presidential Library and Museum (3 hours)
• 16. Anderson Japanese Gardens (1 hour 40 minutes)
• 17. The Morton Arboretum (35 minutes)
• 18. Cantigny Park (40 minutes)
• 19. Frank Lloyd Wright Home and Studio (20 minutes)
• 20. Huron-Manistee National Forests (4 hours)
• 21. Nicholas Conservatory & Gardens (2 hours)
• 22. Oglesby (1 hour 40 minutes)
• 23. White River State Park (3 hours)
• 24. Peoria (2 hours 40 minutes)

Exploring a sleepy river town, fishing in a river surrounded by towering canyon walls, skiing or answering the call of your inner history buff, can leave you feeling relaxed and refreshed. Here are top day trips from Chicago that will awaken your soul and enhance your well-being.

More Features

16 Most Beautiful Resort Spa Baths and Pools

20 Best Romantic Things to Do in Chicago

5 Best Day Trips From Chicago By Train

• --> Conclusion

• About Us/Contact Us
• Privacy Policy
• Terms of Service

• Search Please fill out this field.
• Manage Your Subscription
• Give a Gift Subscription
• Sweepstakes
• Destinations

10 Best Weekend Getaways From Chicago

Waterfalls, wildlife, and lots of small-town charm await.

Elizabeth Rhodes is a special projects editor at Travel + Leisure , covering everything from luxury hotels to theme parks to must-pack travel products. Originally from South Carolina, Elizabeth moved to New York City from London, where she started her career as a travel blogger and writer.

With fascinating architecture, great museums, and plenty of delicious local eateries (deep dish pizza, anyone?), Chicago has a lot to offer tourists and residents alike. That said, we could all use some respite from the urban hustle and bustle every so often. We've rounded up the best destinations within easy reach of the Windy City, from lakeside escapes to state and national parks. Whether you're looking for beautiful landscapes or small-town charm, these quick trips are sure to please every type of traveler. Here are our top 10 weekend getaways from Chicago.

Starved Rock State Park, Illinois

Wander among towering trees to find waterfalls and wildlife at Starved Rock State Park , located on the Illinois River about an hour and a half from Chicago. It's the perfect choice when you want to trade skyscrapers for the great outdoors. In the spring, heavy rains make the waterfalls especially active, and in the fall, the leaves turn beautiful shades of orange, red, and yellow. Stay within the state park at the Starved Rock Lodge , or opt to spend the night in nearby Ottawa, a charming little town with eclectic restaurants, independent shops, and more.

Indianapolis, Indiana

Just a three-hour drive from Chicago, "Indy," as the locals know it, offers plenty to do. Kids will love The Children's Museum of Indianapolis and the Indianapolis Zoo , while sports fans will want to check out the iconic Indianapolis Motor Speedway . The hip Broad Ripple neighborhood has nightlife, dining, shopping, and more, and the Massachusetts Avenue Arts District offers theaters, galleries, and independent boutiques. History lovers can book a stay in one of the 1920s Pullman train car rooms at the Crowne Plaza Indianapolis Downtown-Union Station .

Saugatuck, Michigan

Summer is the perfect time to visit this lakeside town, located just under two and a half hours from Chicago. Lounge on the sandy shores of Oval Beach or Saugatuck Dunes State Park , rent a boat and explore Lake Michigan, browse the art galleries, or check out the local breweries. After a day enjoying some of Lake Michigan's most pristine beaches , rest your head at one of the adorable inns or bed-and-breakfasts in town.

Lake Geneva, Wisconsin

For another nearby waterfront escape, head an hour and a half from Chicago to beautiful Lake Geneva . During the summer, you can get out on the lake, sunbathe on its beaches, or go zip lining, among other outdoor activities. During the winter, check out the Ice Castles , an awe-inspiring display of illuminated, human-made icicles that you can walk through.

Milwaukee, Wisconsin

An hour and a half north of Chicago on Lake Michigan, Milwaukee is teeming with great museums and even better beer. Pabst Brewing Company and Miller Brewing Company call this city home. Today, you can toast to the city's beer heritage by trying these classics or visiting one of the many local craft breweries. The Milwaukee Public Museum is a must-visit — it has fossils, a European village, a full-size display recreating the streets of Milwaukee in the late 19th and early 20th centuries, a butterfly garden, and more. Other sites worth visiting include the Milwaukee Art Museum , the Harley-Davidson Museum , and the Mitchell Park Horticultural Conservatory, also known as The Domes .

Indiana Dunes National Park, Indiana

Just under an hour's drive from the city, Indiana Dunes National Park is perfect for a quick getaway. You can even make it a day trip if you're short on time (it's accessible from the South Shore Line, so you don't even have to drive). This national park covers 15 miles of Lake Michigan's shoreline, making it ideal for a relaxing weekend away from Chicago. Go for a hike along the dunes, fly a kite on the beach, enjoy horseback riding, or check out the historic 1933 World's Fair Century of Progress Homes .

Madison, Wisconsin

Wisconsin's capital city is just over two and a half hours from Chicago, and it offers something for every type of traveler. Food lovers will want to visit the National Mustard Museum and try fresh ice cream at the Sassy Cow Creamery , located 20 miles from Madison. Meanwhile, outdoorsy types will love kayaking or taking a cruise around the lake during the summer, or snowshoeing in the winter. Families can check out the Madison Children's Museum and the Children's Theater of Madison for kid-friendly entertainment.

Holland, Michigan

Holland is a unique destination about two and a half hours from Chicago. The city's Dutch heritage is evident in its famous attractions like the Windmill Island Gardens , De Klomp Wooden Shoe and Delftware Factory , and Nelis' Dutch Village . The yearly Tulip Time Festival is another great reason to head to this quaint Michigan town — millions of tulips are planted across Holland, so visit in spring to see the beautiful flowers in bloom.

Wisconsin Dells, Wisconsin

For a family-friendly getaway, opt for a weekend trip to Wisconsin Dells, a three-hour drive from Chicago. This area, known as the "water park capital of the world," is packed with attractions kids will love. One of them, Noah's Ark Water Park , is the largest water park in the United States. For the ultimate relaxation, take a scenic boat ride through the Dells or visit one of the local wineries or breweries.

Geneva, Illinois

Just an hour outside of Chicago, you'll find Geneva, an ideal destination if you're looking for a small-town getaway. Wander the quaint downtown, check out the murals and outdoor sculptures, and browse independent shops selling antiques, jewelry, chocolate, ice cream, and more. The Fabyan Forest Preserve , with its mid-19th-century windmill, is just a few minutes' drive away.

• Last Updated On
• September 5, 2023

35 Best Weekend Getaways From Chicago — Quick Trips!

There’s no better way to discover the heart of America than through Chicago.

It’s the third largest city in the country, where its skyline meets the shoreline.

And your best weekend getaways from Chicago start the moment you arrive.

Its modern architecture, museums, vibrant music scenes, clubs, and outdoor activities are just some of the many things you can see and do here.

But in a city this vast, you may think and ask what to do and where to stay.

It is a question relatable to many.

As a traveler with years of experience, I visited Chicago and explored its beauty.

I stayed in some of the best properties and toured the city.

And to help you out, I compiled and ranked those places based on different and practical criteria.

Are you keen on knowing more?

Then check out my review with tips below.

Best Weekend Getaways From Chicago Compared

For your best weekend getaway in Windy City, review my guide below.

Editor’s Choice

Four Seasons Chicago

Four Seasons Chicago is the best place where you can marvel at the beauty of the city’s skyline.

• Room Variety: 5/5
• Comfort and Cleanliness: 5/5 
• Location: 5/5
• Affordability: 3/5
• Family-Friendliness: 4/5

#2nd Best Choice

Waldorf Astoria Chicago

If you want exclusivity in your stay in Chicago, choose Waldorf Astoria. It has 215 elegant guest rooms inclusive of oversize bathrooms with tubs.

• Room Variety: 4.5/5
• Comfort and Cleanliness: 5/5
• Family-Friendliness: 

#3rd Best Choice

The Peninsula Chicago

It is a five-star hotel that will surely level up your stay in the city.

• Affordability: 2.5/5
• Family-Friendliness: 5/5

Here are the top 35 weekend getaways in Chicago.

1. Four Seasons Chicago (Editor’s Choice)

120 E Delaware Chicago, IL 60611 (312) 280-8800 Visit Website Social Media Open in Google Maps

Ratings Criteria

• Beautiful city view
• Ideal for business or family trip
• Not so spacious lobby area

Chicago is the home to some of the world’s earliest skyscrapers.

And it is still renowned for its inspiring architectural design.

But it doesn’t stop there.

A luxurious stay here is guaranteed with exceptional service, facilities, and amenities.

Its lobby and lounge are designed ideally for entertainment and socializing.

And its restaurant and bar offer nothing but the perfect taste of Chicago. 

What’s more notable is its perfect location where you can revel in food, drinks, art, and music in the city center.

2. Waldorf Astoria Chicago

11 E Walton St Chicago, IL 60611 (312) 646-1300 Visit Website Social Media Open in Google Maps

• Complete amenities
• Spacious rooms
• Quite expensive

If you want exclusivity in your stay in Chicago, choose Waldorf Astoria.

It has 215 elegant guest rooms inclusive of oversize bathrooms with tubs.

Its suites are furnished with terraces where you’ll see the allure of the city’s skyscrapers right before your eyes.

Surrounded by the city’s highlights, you won’t miss a thing.

Go-to spots, shops, restaurants, and bars are just a breeze away.

And after a long day of being a tourist in Chicago, its spa and indoor lap pool is just waiting for you.

Or better yet, stay in your room or sit on the terrace and appreciate the glowing Chicago at night.

3. The Peninsula Chicago

108 E Superior St Chicago, IL 60611 (312) 337-2888 Visit Website Social Media Open in Google Maps

• Unsurpassed service
• Nice location
• Too expensive for what it offers

Whether it’s a weekday or weekend getaway you’re in, The Peninsula Chicago is just a step away.

Each part of it is designed for your perfect Chicago getaway.

Everything is incomparable, from its sophisticated rooms and suites to its fancy restaurant and rooftop spa.

Do you intend to stay longer?

Think about it as your third night is on them when you book at least three consecutive nights.

That’s a pretty reasonable offer, quite hard to resist.

Moreover, almost every must-visit spot is just a walk away from this property.

4. Grand Geneva Resort & Spa

7036 Grand Geneva Way Lake Geneva, WI 53147 (262) 248-8811 Visit Website Social Media Open in Google Maps

With its luxurious facilities, this 1,300 acres of AAA Four-Diamond resort is an excellent alternative to Waldorf Astoria Chicago and The Peninsula Chicago.

This resort encompasses 1,300 acres of countryside in Wisconsin.

It features two lodging options: The Grand Geneva and the Timber Ridge.

By car, Grand Geneva Resort & Spa is 1 hour and 27 minutes away from Chicago.

Enjoy an incredible getaway with the family in this popular resort.

The kids will enjoy the resort’s health and fitness facility, with its programs crafted especially for them.

They can participate in many kid-friendly activities in the adventure center, too.

If they prefer outdoor activities, they can go horseback riding or meet the animals in the zoo instead.

As for the adults, how does a spa treatment sound?

If you opt for physical activities, you can play water sports in Timber Ridge’s park or go wall climbing in the gym.

5. Milwaukee

Milwaukee, WI (414) 286-2489 Visit Website Social Media Open in Google Maps

This city in Wisconsin encompasses over 61,000 acres of land on Lake Michigan’s western shore.

It features breweries, museums, and event venues.

If you’re coming from Chicago, you can reach Milwaukee in 1 hour and 27 minutes.

Here’s one cool overnight trip you won’t forget.

Milwaukee has everything you need for the best weekend adventure.

Want some history?

Check out the Milwaukee Public Museum, with its beautiful recreation of the city at the turn of the 20th century.

If you’re more into nature, the Mitchell Park Horticultural Conservatory is the perfect destination.

It features three domes that each function as a greenhouse and botanical garden.

Enjoy the blushing peonies and firs for the complete nature experience.

Recommended Hotel: The Pfister Hotel

Related: Fun Day Trips From Milwaukee

Related: Hotels in Chicago

6. Indiana Dunes National Park

1215 North State Road 49 Porter, IN 46304 (219) 395-1882 Visit Website Social Media Open in Google Maps

This park stretches for 15,349 acres in northwestern Indiana.

It’s home to a visitor center, park trails, and historical structures.

The travel time from Chicago to Indiana Dunes National Park is 42 minutes.

Are you looking for short trips from Chicago for your weekend getaway with friends?

Head to the Indiana Dunes National Park.

Hike the Dunes Succession Trail, with its vast array of paths perfect for adventurers.

Wear comfortable shoes because you’ll have to walk sandy and wooden trails at the same time.

If you’re up for a challenge, climb 192 feet to the top of Mount Tom.

You’ll get rewarded with stunning views of the dunes and the lake.

Recommended Hotel: Spring House Inn

Madison, WI (608) 255-2537 Visit Website Social Media Open in Google Maps

Madison is the capital city of Wisconsin.

It’s on an isthmus surrounding Mendota, Monona, Waubesa, and Kegonsa lakes.

It’s also home to botanical gardens and architectural gems like the Wisconsin State Capitol.

You can reach Madison from Chicago in 2 hours and 18 minutes if you use a vehicle.

Madison is one of the best places near Chicago for vacation.

Visit any of the city’s nine national historical landmarks, including Jacobs I, a single-family home constructed in 1937.

Not much of a history buff?

Marvel at Jacobs I’s architecture instead.

The home built by architect Frank Lloyd Wright has been touted as the first Usonian home.

The Wisconsin State Capitol is a must-see, too, with its majestic dome and elegant gilded bronze statue on top.

Recommended Hotel: The Madison Concourse Hotel

Holland, MI (616) 355-1370 Visit Website Social Media Open in Google Maps

Spanning over 11,000 acres, Holland is the largest city in Ottawa and Allegan counties.

It’s a popular tourist destination for its rich Dutch heritage.

From Chicago, Holland is only 2 hours and 33 minutes away by car.

If you’re looking to have the perfect weekend getaway, Chicago and its nearby areas offer many options.

Chicago has beautiful parks and skyscrapers.

Meanwhile, Holland has deep Dutch roots evident in many of its landmarks.

In the Windmill Island Gardens, you’ll find the last working mill allowed to leave The Netherlands in 1964.

Check out Nelis’ Dutch Village, too.

The amusement park is home to a gorgeous reproduction of an 1800s Dutch village.

Recommended Hotel: CityFlatsHotel Holland, Tapestry Collection by Hilton

9. Wisconsin Dells

Wisconsin Dells, WI (608) 254-4636 Visit Website Social Media Open in Google Maps

Nestled on the Wisconsin River, this city stretches over 5,200 acres in Adams, Columbia, Juneau, and Sauk counties.

It features a wide array of water parks and nature spots.

You can reach Wisconsin Dells in 2 hours and 56 minutes if you’re driving a car from Chicago.

You and the kids will agree this is one of the best getaways in Chicago and nearby.

After all, who doesn’t like swimming in beautiful blue waters and going down long slides?

If you get tired of swimming in water parks, go on a duck boat tour instead.

Marvel at the beautiful creatures while floating on Lake Delton under the blue Wisconsin skies.

Recommended Hotel: Hilton Garden Inn Wisconsin Dells

Related: Restaurants in Wisconsin Dells, Wisconsin

Related: Weekend Vacations in Illinois

Geneva, IL (630) 232-7494 Visit Website Social Media Open in Google Maps

Geneva is in Kane County, located on the western side of Chicago.

It features an extensive bike trail system and historical sites, some dating back to the 1800s.

It’s a 49-minute drive from Chicago to Geneva.

Geneva is just the place to be if you want to bond with your significant other.

The city is one of the best romantic getaways from Chicago for its natural beauty.

Take a stroll in the beautiful Fabyan Forest Preserve.

Amid the lush greenery stands the majestic Fabyan Windmill, built between 1850 and 1860.

Check out the Fabyan Japanese Garden, too.

It’s a lovely oasis with a small pond and flora that stand out.

Recommended Hotel: Comfort Inn & Suites Geneva- West Chicago

11. Fox River Valley

Fox Valley Aurora, IL 60504 (630) 256-4636 Visit Website Social Media Open in Google Maps

Also known as the Fox Valley, this region extends from Antioch in northern Illinois to Ottawa in the south.

It’s home to the Fox River Trail, green spaces, and water bodies.

The travel time from Chicago to the Fox River Valley is 42 minutes.

This place will make any traveler’s list of inexpensive weekend getaways near Chicago.

The Fox River Valley, after all, is pure nature anyone can explore.

Bike a portion of the 32-mile Fox River trail for stunning views of Carpenters Dam and Tyler Creek.

You can rent a kayak if you prefer a water adventure.

Soak in the gorgeous nature views while gliding along the Fox River.

Recommended Hotel: Best Western Oswego Hotel

12. Harbor Country

Three Oaks, MI (269) 469-5409 Visit Website Social Media Open in Google Maps

This region consists of eight towns in southwest Michigan: New Buffalo, Three Oaks, Lakeside, Harbert, Michiana, Grand Beach, Sawyer, and Union Pier.

It features gorgeous beaches and wineries.

You can get to Harbor Country from Chicago in 1 hour and 12 minutes.

Harbor Country differs from many Chicago weekend getaways.

Unlike your cheap Chicago vacations, this one entails a bit of shelling out money.

After all, Harbor Country is an upscale weekend getaway destination.

Think of it as the Hamptons of New York or the Cape Cod of Boston.

But even if you’d need to shell out a bit, it’s worth it.

You can enjoy the region’s beaches with delicious wine.

Then spend the night in a luxurious bed and breakfast with amenities.

Recommended Hotel: Fairfield Inn and Suites New Buffalo

13. St. Joseph

St. Joseph, MI (269) 983-5541 Visit Website Open in Google Maps

This city stretches for over 3,000 acres on the shores of Lake Michigan.

It’s home to the sandy Silver Beach and parks.

You can get to St. Joseph in 1 hour and 35 minutes if you’re coming from Chicago.

If you prefer cheap vacations from Chicago, head to St. Joseph.

The city is a nature oasis you can enjoy anytime.

Have a picnic on the Silver Beach shore and enjoy the beautiful landscape.

If you prefer a more strenuous activity, go swimming in the gorgeous blue waters.

Are you a fitness enthusiast?

Go on a hike for your dose of exercise in Tiscornia Park.

Recommended Hotel: The Inn at Harbor Shores

14. South Haven

South Haven, MI (269) 637-0700 Visit Website Social Media Open in Google Maps

This city encompasses 2,240 acres of land in Van Buren and Allegan counties.

It features a gorgeous harbor and beaches.

If you’re driving from Chicago, you can reach South Haven in 2 hours and 2 minutes.

Commune with nature in this popular tourist destination.

The city’s seven public beaches aren’t just the perfect spots for swimming.

They make for beautiful pictures, too, with their gorgeous sea waters and shores.

If you get tired of the beach, check out the beautiful South Haven harbor.

Enjoy the stunning water views, then walk downtown for the perfect meal.

Recommended Hotel: Hampton Inn South Haven

Gurnee, IL (847) 599-7500 Visit Website Social Media Open in Google Maps

This village borders Waukegan in the Chicago metropolitan area.

Located 35 miles from Chicago, it’s home to the Six Flags Great America amusement park.

If you drive a vehicle from Chicago, you can get to Gurnee in 50 minutes.

Enjoy pure family fun in Gurnee, with its amusement park known for its adrenaline-pumping rides.

Try all 17 of Six Flags’ heart-stopping roller coasters for the complete adventure.

But if you’re not a thrill-seeker, don’t worry.

You can enjoy the park’s entertaining shows instead.

Or just explore Gurnee Mills, a mall that features over 170 stores.

Recommended Hotel: Country Inn & Suites by Radisson, Gurnee, IL

16. South Bend – Indiana

South Bend Indiana, United States (574) 233-0311 Visit Website Social Media Open in Google Maps

An hour and 44-minute drive from Chicago lies South Bend, Indiana.

It’s a great day trip destination to explore more of what’s outside Chicago.

This city is home to the University of Notre Dame, a prestigious university known for its gold-domed main building.

And if you proceed to the city center, you’ll witness its thriving art scene.

There lies the Studebaker National Museum which has numerous displays of classic cars.

Morris Performing Arts Theater, a 2,564-seat concert hall, is a shouldn’t-miss part, too.

Surely you’ll see all the must-sees in the city within a day; a perfect place for your weekend getaway from Chicago.

Recommended Hotel: Antioch Inn & Suites Near Gurnee

17. Lake Geneva

Lake Geneva, WI (262) 248-3911 Visit Website Social Media Open in Google Maps

Located on Geneva Lake, this resort city features gorgeous beaches, parks, and Gilded Age mansions.

It is 65 miles northwest of Chicago.

If you use a car, you can get to Lake Geneva in 1 hour and 24 minutes.

Head to Lake Geneva, and you’ll see why it’s one of the best long weekend trips from Chicago.

Although small in size, the city has a lot to offer the traveler.

Explore Shore Path for stunning views of spectacular mansions, some dating back to the 1800s.

Check out the Stone Manor built by real estate magnate Otto Young in 1899.

Blackpoint, constructed in 1888 by Chicago beer baron Conrad Seipp, has 74 species of evergreen trees in front of his mansion.

If you’re not into architecture, you can immerse in nature instead.

Ride a boat on the 5000-acre Geneva Lake and soak in the beautiful views.

Recommended Hotel: Mill Creek Hotel

18. Turkey Run State Park

8121 Park Road Marshall, IN 47859 (765) 597-2635 Visit Website Open in Google Maps

This park, created in 1916, is Indiana’s second state park.

It stretches for 2,382 acres of land in Parke County.

It’s also home to historical sites, a pool, and public sitting areas.

If you use a vehicle, the travel time from Chicago to Turkey Run State Park is 3 hours.

You won’t run out of things to do in this park.

Experience nature at its finest while hiking a portion of the 14 miles of trails with varying degrees of difficulty.

Are you a history enthusiast?

The park has individual sites listed on the National Register of Historic Places.

Check out the Lusk Home and Mill Site, which date back to 1822 and 1826, respectively.

The Richard Lieber Log Cabin, built in 1848, is a must-see, too.

Recommended Hotel: Turkey Run Inn & Cabins

19. The American Club Resort Hotel

419 Highland Drive Kohler, WI 53044 (800) 344-2838 Visit Website Social Media Open in Google Maps

Built in 1918 as a male dormitory for Kohler employees, this lodging institution is now a five-star hotel that offers wellness and recreational opportunities.

By car, The American Club Resort Hotel is 2 hours and 22 minutes away from Chicago.

Who says you can’t have some incredible me-time in one place?

At The American Club Resort Hotel, you can.

Have the ultimate relaxing experience at the Kohler Waters Spa.

After your spa, enjoy your favorite book in the hotel’s reading area.

You can also check out the Kohler Design Center instead, with its stunning bathroom designs.

Enjoy an upscale meal in The Immigrant for the perfect bonding moment with yourself.

20. Whistling Straits

N8501 Lakeshore Road Sheboygan, WI 53083 (800) 444-2838 Visit Website Social Media Open in Google Maps

This luxury golf resort, owned by Kohler Company, is along the Wisconsin coastline.

The resort consists of two golf courses: the Straits and the Irish.

You can reach Whistling Straits in 2 hours and 28 minutes if you travel by car from Chicago.

If you love golf, Whistling Straits should be your go-to place.

Enjoy state-of-the-art 36-hole links-style golf courses set against a beautiful nature landscape.

Whistling Straits offers incredible views of Lake Michigan and rolling hills.

The Irish, meanwhile, will transport you to the gorgeous European country with its rugged coastline and smooth grassy terrain.

You won’t just get to play your favorite sport here.

Recommended Hotel: Harbor Winds Hotel

21. Parke County

Parke County, IN (765) 569-3394 Social Media Open in Google Maps

This rural county stretches for over 284,000 acres of land along the Wabash River.

It lays claim to being the Covered Bridge Capital of the World.

If you’re coming from Chicago, Parke County is 3 hours and 26 minutes away by car.

Do you love architecture?

Go on a weekend getaway to Parke County, then.

You need more than enough time to visit the county’s 31 covered bridges, each with its unique architectural design.

The Portland Mills Covered Bridge is a must-see.

Built in 1856, it’s a single-span Burr Arch truss-covered bridge that’s also the second oldest in the county.

Check out the Jackson Covered Bridge, built on a base of hewn stone in Rockport.

Constructed in 1861, it’s the oldest standing bridge built by the acclaimed J.J. Daniels.

Galena, IL (815) 776-9200 Visit Website Social Media Open in Google Maps

This city in Illinois is the largest in Jo Daviess County.

Located in an unglaciated area in the northwest portion of the state, it’s famous for its rolling hills and 19th-century architecture.

Galena is a 3-hour drive from Chicago.

Although a city by classification, Galena exudes a small-town vibe, making it a popular destination.

Picture gorgeous red-brick structures lining the main road where traditional carriages occasionally ply.

Go kayaking along the river to experience stunning views of nature wherever you look.

You can walk through native prairies and interact with goats here, too.

Cap off your weekend with a challenging game of golf on any of the city’s 11 picturesque courses.

Recommended Hotel: Country Inn & Suites by Radisson, Galena, IL

23. Dubuque

Dubuque, IA (563) 589-4100 Visit Website Social Media Open in Google Maps

Nestled along the Mississippi River, Dubuque encompasses over 19,000 acres of land at the junction of Iowa and Wisconsin.

It’s a go-to place for its unique architecture and historical sites.

You can get to Dubuque from Chicago in 3 hours and 16 minutes by car.

Dubuque is heaven for architecture and history buffs.

Head downtown, and you’ll find the Dubuque County Courthouse.

It’s in the Beaux Arts architectural style, built from 1891 to 1893.

The Holy Ghost Catholic Church in the North End is a must-see, too.

Formed in 1896, the beautiful church’s Romanesque Revival style stands out.

In the South End, check out St. Raphael’s Cathedral.

The church traces its roots way back in 1833.

Enjoy its Gothic Revival Style amid Dubuque’s nature landscape.

Recommended Hotel: Hotel Julien Dubuque

24. Field of Dreams

28995 Lansing Road Dyersville, IA 52040 (563) 875-8404 Visit Website Social Media Open in Google Maps

Built in 1988 for the movie Field of Dreams, this baseball field now functions as a sports venue and pop culture destination.

It’s also home to a souvenir shop and a 2,600-square-foot barn that serves as an event center.

By car, Field of Dreams is 209 miles away from Chicago. So you can get to the iconic baseball field in approximately 4 hours.

This isn’t your ordinary baseball field.

It has pop culture significance as the filming site of the Academy Award-nominated movie Field of Dreams.

So when you get to the place, you can also tour the Kinsella family house as shown in the movie.

You can also purchase official Field of Dreams apparel from Baseballism, the movie’s on-site official retail store.

Spend a night in the newly remodeled three bed-room farmhouse for the complete movie experience.

Recommended Hotel: Super 8 by Wyndham Dyersville

25. Ann Arbor

Ann Harbor, MI (734) 794-6000 Visit Website Social Media Open in Google Maps

This city stretches for over 18,600 acres in the Midwestern state of Michigan.

It is home to the University of Michigan, museums, and parks.

The travel time from Chicago to Ann Arbor is 4 hours and 33 minutes by car.

Ann Arbor has everything you need for the perfect weekend getaway.

The University of Michigan Museum of Art will give you a one-of-a-kind artistic experience, with its collection spanning over 150 years.

If you’re more of a history buff, the Kelsey Museum of Archaeology is just the place for you.

It’s home to over 100,000 artifacts, including mummies.

Don’t worry if you’re not much of a museum-goer.

Ann Arbor has gorgeous parks you can explore, too.

Go paddle-boarding on the Huron River for fantastic views of the Michigan skies, flora, and fauna.

You can also hike the trails of Gallup Park and explore its 69 acres of open green spaces and water bodies.

Recommended Hotel: Graduate Ann Arbor

26. Traverse City

Traverse City, MI (231) 947-1120 Visit Website Social Media Open in Google Maps

This city stretches for over 5,500 acres in Grand Traverse and Leelanau counties.

It’s the largest city in the Northern Michigan region.

It’s home to beaches, at least 30 public parks, and historical sites.

By car, you can get to Traverse City in 5 hours and 8 minutes if you’re coming from Chicago.

The trip from Chicago to this city may take longer than your usual day trips outside.

However, it’s worth it.

Immerse in history with a tour of landmark sites, such as the City Opera House and Novotny’s Saloon.

Take the kids to Indian Woods Park, where they can also use playground equipment in a beautiful nature landscape.

If you want some physical activity, try hiking.

Just take your pick from the over 30 trails that meander through gorgeous woodlands and open green spaces in the city.

Recommended Hotel: Country Inn & Suites by Radisson, Traverse City, MI

27. Louisville

Louisville KY (502) 379-6109 Visit Website Social Media Open in Google Maps

Nestled on the Ohio River, Louisville is Kentucky’s largest city.

It features boxer Muhammad Ali’s home, some Fortune 500 companies, and a wide array of dining options.

If you’re driving from Chicago, you can reach Louisville in 4 hours and 47 minutes.

Experience the big city life in Louisville.

Marvel at the gorgeous skyscrapers that jut into the Kentucky skies.

The 400 West Market stretches 549 feet above the ground.

A close second is the National City Tower, with a height of 512 feet.

Then head to Mall St. Matthews for your shopping needs.

The mall features over 140 specialty retailers, which means you’re bound to find something to take home.

Recommended Hotel: The Brown Hotel

28. St. Louis

St. Louis, MO (314) 421-1023 Visit Website Social Media Open in Google Maps

This city is along the Mississippi River.

Commonly known as the Gateway to the West, the city has independent frontier-town roots and a vibrant blues music scene.

From Chicago, St. Louis is 4 hours and 35 minutes away by car.

If you love history, don’t miss out on St. Louis.

The city is home to majestic structures, some of them dating way before the Civil War.

Drop by the Basilica of St. Louis, built between 1831 and 1834.

The Christ Church Cathedral is a must-visit, too, with its Gothic Revival style completed in 1867.

Don’t forget to check out the arch that gave St. Louis its Gateway to the West moniker.

Completed in 1965, the long arch is also an architectural beauty, standing 630 feet tall.

Recommended Hotel: Angad Arts Hotel

Related: Fun Day Trips From St Louis

Zion, IL (847) 746-4000 Visit Website Social Media Open in Google Maps

This city encompasses over 6,300 acres of land in Lake County at an elevation of 187 meters.

It boasts beautiful parks and historical structures.

You can get to Zion in 58 minutes if you’re coming from Chicago.

Have the ultimate nature experience in Zion, with its 24 parks offering incredible views of flora.

Go biking through Edina Park, with its serene pond and open spaces

Hermon Park is perfect for picnics, with its tall trees surrounding green grass.

If you still have energy for more workout activities, hike a portion of the trail that cuts through Carmel Park.

You’ll get stunning views of the clear Illinois skies and lush greenery.

Recommended Hotel: The Inn On Sheridan

30. Elkhart Lake

Elkhart Lake, WI (920) 876-2231 Visit Website Social Media Open in Google Maps

This village in Sheboygan County runs along Elkhart Lake.

It’s famous for its natural beauty, museums, and road race events.

If you drive from Chicago, you can reach Elkhart Lake in 2 hours and 30 minutes.

You’ll enjoy your weekend getaway in Elkhart Lake with the tons of activities you can do here.

Hike the 3.35-mile segment of the Ice Age National Trail for beautiful views of rolling hills.

If you get tired of hiking, visit Road America, which stretches over 4 miles around the lake.

The track that has been around since the 1950s continues to host racing events.

Time your visit to the city based on the racing schedule so you can attend one.

Recommended Hotel: Baymont by Wyndham Plymouth

31. Richland County

Richland County, WI (608) 647-8821 Visit Website Social Media Open in Google Maps

This county stretches for 376,960 acres in southwestern Wisconsin.

Richland County is home to Frank Lloyd Wright architecture, parks, and museums.

Richland County is 3 hours and 37 minutes away from Chicago by car.

Richland County has something to offer, whether you’re a history buff or a nature enthusiast.

Check out the Albert D. German Warehouse, designed by acclaimed architect Frank Lloyd Wright in 1915.

You can unwind at Alana Springs Campground, where you can set up your tent amid gorgeous nature.

The Pier County Park is a must-see, too, with its layered and blocked sandstone rising for about 60 feet.

Recommended Hotel: Ramada by Wyndham Richland Center

Related: Best Weekend Getaways From Minneapolis

32. Door County

Door County, WI (920) 743-5511 Visit Website Open in Google Maps

Situated on a peninsula between Green Bay and Lake Michigan, Door County is home to many beaches and parks.

Chicago is 244 miles away from Door County.

If you travel from Windy City by car, you can get to Door County in 3 hours and 48 minutes.

Door County has a little bit of everything for everyone.

For the nature buff, Cave Point County Park is a must-visit.

The park is home to gorgeous underwater caves and limestone cliffs you can explore.

For the history enthusiast, check out the Eagle Bluff Lighthouse, built in 1868.

The Door County Maritime Museum is a great destination, too, with its comprehensive exhibits on Great Lakes history.

Door County even has something for the wine lover.

Enjoy delightful wines made from California grapes in Stone’s Throw Winery.

Recommended Hotel: Gordon Lodge

33. Vilas County

Vilas County, WI (715) 479-3600 Visit Website Open in Google Maps

This county stretches for 548,480 acres in northern Wisconsin.

It’s home to nearly 90 scenic forest trails and over 1,300 lakes.

From Chicago, the drive to Vilas County will take you 5 hours and 44 minutes.

It’s quite a long journey from Chicago to Vilas County.

But when you get to the place, you’ll conclude the trip is worth all your time and effort.

After all, the place is a nature oasis.

Go boating on Eagle Lake and soak in the gorgeous lush greenery around you.

You can hike the 1.5-mile loop near Eagle River afterward.

Whatever you do, you’re in for a beautiful nature immersion.

Recommended Hotel: Hiawatha Lodge Inn

34. Shawnee National Forest

Herod, IL 629646 (618) 253-7114 Visit Website Social Media Open in Google Maps

Nestled in southern Illinois between the Ohio and Mississippi Rivers, this national forest stretches for 289,000 acres.

It’s home to forests, lush canyons, and ridges.

The travel time from Chicago to Shawnee National Forest is 5 hours and 25 minutes.

Travel to one of nature’s wonders for the perfect weekend trip.

Experience Cedar Lake a different way, on board a beautiful horse and under the gorgeous Illinois skies.

You can hike in the park if you prefer to walk.

How about exploring a portion of the 160-mile River Trail that will take you to gorgeous forest streams and greenery?

Recommended Hotel: Baymont by Wyndham Marion

35. Pictured Rock National Lakeshore

N8391 Sand Point Road Munising, MI 49862 (906) 387-3700 Visit Website Social Media Open in Google Maps

This tourist destination encompasses the south shore of Lake Superior in Michigan.

It’s home to unusual sandstone formations and shipwrecks.

You can reach Pictured Rock National Lakeshore in 6 hours and 12 minutes by car.

This is one of the best weekend getaways from Chicago for a reason.

The place is a visual treat, with its magnificent cliffs.

The cliffs can go as high as 200 feet above sea level, with formations ranging from human profiles to castle turrets.

Bring your camera because you’ll want to take pictures of everything here.

Recommended Hotel: Comfort Inn & Suites Munising – Lakefront

Getaway Guide 

Comparing destinations: which one is right for you.

Knowing the pros and cons of each destination will help you decide which one is ideal for you.

And remember that your preference also plays a vital role in picking what’s best.

The Four Seasons Chicago lives up to what it promises guests: a luxurious and relaxing stay.

But for years in business, some parts need an update already.

Meanwhile, Waldorf Astoria Chicago is indeed a luxury hotel with unsurpassed facilities and amenities, but it also comes with a high cost.

On the other hand, The Peninsula Chicago has everything you need and expect from a five-star hotel.

But just like other luxury hotels, it’s also quite expensive.

Finally, Grand Geneva Resort & Spa has an array of activities for fun and relaxation for everyone.

But its customer service could be better. 

How I Picked The Destinations 

With years of experience as a blogger and traveler, I have learned much about picking the best destination and property to stay.

I thoroughly researched where to stay and what to do in Chicago.

My fellow travelers also gave reliable suggestions, and when I got there, I tried them myself.

My research and experience in the city strengthen my conclusion of what’s best.

Our Property Rating Method 

I rate these properties based on the following criteria:

• Room Variety: I use this to rate the room options offered by every property. What room types are available? Can it accommodate different budgets, group sizes, and preferences? I ask myself these questions when evaluating the property’s room variety. 
• Comfort and Cleanliness: This measures the overall cleanliness and comfort of the accommodations. Does it have comfortable beds? Are the rooms spotless and dust-free? These are important factors I consider when rating comfort and cleanliness. 
• Location: This is used to evaluate how convenient and accessible the property is. How close is it to the attractions? Are there good public transportation options near the location? Is it easily accessible for families? These questions are important when I rate the location of every accommodation. 
• Affordability: I use this to evaluate the property’s affordability. Are the room rates reasonable? Does the property have any additional fees? Does the property offer discounts or packages? I ask myself this in order to rate affordability. 
• Family-Friendliness: This evaluates the family-friendliness of each property. Does it offer babysitting services and children’s activities? Does it have connecting rooms for families? I use these questions to rate the family-friendliness of the property. 

Frequently Asked Questions 

What are cities 3 hours from chicago.

Milwaukee, Rockford, and Michigan City are within a two-hour drive from Chicago.

How Far Is Lake Geneva From Chicago, And What Can I Do There?

Lake Geneva is about a 90-minute drive from Chicago. It offers a range of activities including boating, fishing, golfing, hiking, and skiing in the winter. The area is also home to several spas and wellness centers.

A stay in a property with a perfect location will give you nothing but only the best weekend getaways from Chicago. 

My Waldorf Astoria Chicago experience was beyond impressive.

I had a relaxing and with-a-view room.

The excellent location for shopping and restaurants was what I love most about The Peninsula Chicago.

And the variety of activities I did at Grand Geneva Resort & Spa was immense.

My favorite was the view of the calm lake

But the top pick of the bunch is the Four Seasons Chicago.

The welcoming staff, fancy and modern facilities, and countless amenities made me enjoy my stay. 

During my stay at the Four Seasons Chicago, I particularly enjoyed their renowned spa, indulging in a rejuvenating massage and a soothing swim in the indoor pool.

My family and I savored the diverse breakfast options, with my children relishing the fluffy pancakes. 

When exploring the surrounding areas, we appreciated the hotel’s proximity to the iconic Magnificent Mile, making it easy to shop and dine.

My kids had a blast at the nearby Navy Pier, where we enjoyed a fun-filled afternoon. 

Four Seasons Chicago offered the ideal blend of relaxation and adventure for our family getaway.

Join my monthly email! Sign up

19 Awesome Road Trips from Chicago (with Timings)

Keeping your introduction to road trips from Chicago short and simple, let’s take a look at the summer, winter and weekend favourites!

The city of Chicago is awesome and all, but it’s also a great starting point for some great Chicago road trips. The city’s prime location acts as a portal to the Midwest – from historical cities to sprawling state parks and urban-stress-relieving beer. 

Best Chicago Road Trips in Summer

If you’re looking for one of the longest Chicago road trips, how about driving from Chicago to New Orleans ? If you’re thinking a little shorter, then read on…

Distance: as far as you can go

No American road trip is complete without covering some part of classic Road 66 – of which, lucky for us, kicks off in Chicago!

Snap a selfie at the official sign between East Adams and South Michigan Avenue then check-off stops such as the Gemini Giant, the Pontiac murals, Lincoln Presidential Library and more. If you can spare a month, make it all the way down to the Pacific Ocean.

2. Illinois’ Great River Road

Distance: 3.5-hour drive

In a seemingly never-ending chain of historical sites and activities, the drive along Mississippi River to East Dubuque is one of the best road trips from Chicago.

Moline and Rock Island are two cool detours but you can head straight for East Dubuque for its Chicago Great Western Railway Depot Museum. John Deere Pavilion lets you hop from car to farm machines, while the city Nauvoo shows off many historic homes. 

3. Lake Michigan to South Haven

Distance: 2.5-hour drive

Escape the heat by packing your car with beach gear and setting off for a nice drive around Lake Michigan and towards South Haven.

There are plenty of berry farms along the way so you can stain your hands with blueberries; or maybe you prefer to climb up a lighthouse?

To take your road trip even further, bring a bike! Cruise along the water front; take a dip or two. 

Do you have a favourite road trip quote? Click for the best long drive quotes to inspir e your next adventure!

4. Shawnee National Forest

Distance: 6-hour drive

One of the longest Chicago road trips on the list, it’s more than worth it to visit Shawnee National Forest. In fact, plan to camp amidst the spectacular range of landscapes for one of the best driving trips from Chicago!

Local favourites include the Garden of the Gods – you’ll find super special rock formations like Anvil Rock. Little Grand Canyon and Bell Smith Springs feature moderate hikes; Inspiration Point offers panoramic views over the prairie, Mississippi River and the forest.

Not convinced? Shawnee Hills Wine Trail is a brilliant drive that links up vineyards and wineries in the area – a great stop on a road trip from Chicago.

How about driving from Chicago to Atlanta? Here’s my guide to the best stops on a Chicago to Atlanta road trip , just for you.

Best Chicago road trips in Winter

If you want the best road trips from Chicago when it’s colder and darker, then these are the best ones for you.

5. Grand Rapids

Distance: 3-hour drive

After just long enough of a drive, pull into Grand Rapids for a nice sweep of activities. The Beer City Ale Trail will keep you road-tripping on foot (or car, if you have a Designated Driver); or wander through Downtown Market for food adventures instead.

Warmed by booze, drop by the 158-acre Frederik Meijer Gardens & Sculpture Park where their installations are bright pops of colour against an all-white backdrop. 

6. Muskegon

Speaking of unusual winter activities, I’ve heard so much about Muskegon Winter Sports Complex. Just an hour from Grand Rapids, it’s a great next stop on your Chicago road trip.

Their Olympian-designed ice-luge course is perfect for beginners, spanning 850 feet of forested speed racing. Muskegon is also home to USS Silversides Submarine Museum if you’re into marine vehicles, and there’s a great pier and lighthouse too.

7. Indianapolis

When temperatures are cold, cold, cold – you might opt for staying indoors. The city of Indianapolis is one of the best road trips from Chicago during winter because of its incredible indoor entertainment: museums.

From the Indianapolis Museum of Art to the Indianapolis Children’s Museum to quirky Indiana Medical History Museum, you can escape the cold all day!

Of course, drop by famous City Market for great eats and then maybe go on a catacombs tour underground too. This makes for one of the best road trips from Chicago.

8. Boyne Mountain Resort

Distance: 5-hour drive

Michigan winters are best captured with the ski resort of Boyne. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades.

While the forested grounds offer romantic snow-covered views, don’t miss out on the epic zip lines that take you through the trees and slopes. 

If you like your road trips from Chicago with a bit of snow and ski thrown in, then this is a great option for you.

Your ESTA for the USA

Before you go to the USA make sure you have your ESTA organised. You can find help with this on this link: https://www.application-esta.co.uk/ESTA-guide . It doesn’t take long and organising it beforehand will make things go that bit smoother at the airport.

9. Apostle Islands

Distance: 7-hour drive

Does driving over ice count as going off-road?

It’s an unforgettable journey to Apostle Islands National Lakeshore as winter ice freezes thickly to transform water into road, ending with stunning ice caves!

Make sure to visit the only inhabited Madeline Island as well for a cool wind sled experience and hot tub stay. 

Day Road Trips from Chicago

10. lake geneva.

Distance: 1.5-hour drive

Chicago’s number one when it comes to day trips, Lake Geneva is one of the best lake town’s in the US.

Downtown boasts all the food and drinks you need for the inevitable food baby; you might even land a booze cruise.

Hot air balloon rides, Lake Shore Path, ziplines and even ski slopes make it a year-round place to visit. It’s a multi-visit destination for sure!

11. Harbor Country

Distance: 1-hour drive

Wind between the towns of Michiana, Grand Beach, Three Oaks, New Buffalo, Lakeside, Union Pier, Harbert and Sawyer. This Chicago road trip will have you hopping between wineries and breweries, not to mention the beach.

It’s so close to the city, but the sand dunes and soft grasses make it a wholly different world. 

12. Starved Rock State Park

Distance: 2-hour drive

Families and romantics will love Starved Rock State Park for reasons that include: 13 miles of hiking, 18 canyons, free entry and nature-surround lodge.

It’s a great location to unplug for a day as you hunt down natural rock pools, waterfalls and incredible moss-strewn glades. You can even visit in the winter for cross-country skiing and cuddles in front of expansive mountain views. 

13. Saugatuck 

Making up Lake Michigan’s “art coast of Michigan”, Saugatuck and its neighbours (Fennville and Douglas) are house dozens of art galleries!

Unique and LGBTQ+-friendly shops feature alongside artsy hubs to make it a super welcoming town. Of course, famous Oval Beach appeals with soft dunes and paddleboat rides too. From craft booze tours to fruit picking and corn mazes, it’s one of Chicago’s best road trips.

14. Elkhart Lake

I won’t spoil it for you but this 292-acre lake and nearby Kettle Moraine State Forest is truly a place to unwind from the crowds.

You can hike the epic Ice Age National Scenic Trail or bike down Old Plank Road Trail. Pumpkin patches, race-tracking and fishing are all inclusive!

Want a charming hideaway? This is it.

Road Trips 4 hours from Chicago

Want your road trips from Chicago for a special weekend? Then these Chicago road trips are only 4 hours away.

15. Ann Arbor

If you’re looking for an all-season destination, Ann Arbor is the perfect road trip from Chicago.

Huron River entertains with kayaking, paddle-boarding, tubing and swimming; Matthaei Botanical Gardens and Nichols Arboretum displaying beautiful foliage. Definitely spare some time for Kerrytown Market and Shops for all their indie offerings! 

16. Door Country

Also called ‘Cape Cod of the Midwest’, Door Country is a 70-miles-long basket of fun!

You’ll never get tired of exploring its orchards, coves, lighthouses and wineries. Away from the light pollution, Newport State Park offers stunning starlit skies while Ephraim is all the small-town charm you need. Just imagine – 300 miles of coastline.

You can reach Galena under 4 hours but I recommend taking your time. Pull up through scenic rolling hills to go back in time because the Galena Historic District is made up of cobblestone streets and over 1,000 buildings from the 19 th century.

For those non-history buffs, Chestnut Mountain opens as a ski resort in the winter; Stagecoach Trail and Apple River Canyon State Park are open year-round. 

18. Richland County

To really escape from people, Richland County is a rural road trip destination where you can bunk for the night. But away from the isolated and lush property of Candlewood Cabins are fields and hills that keep you outdoors all day.

The Ridge Road and Pine River Recreation Trail fulfils all your adventurous needs – where else would you find wildlife while biking over abandoned railroads?

You also have three rivers and five state parks within an hour’s distance, and the lovely 100-mile Lower Wisconsin River Scenic Byway for more driving way. 

19. Huron-Manistee National Forest

Michigan really surprises us again and again!

Along the peninsula is the expansive Huron-Manistee National Forest, one of the best road trips from Chicago if you are a nature enthusiast. A single paved road takes you through dense forest (beautiful in the fall) to parking areas so you can hike your way through the serene space or canoe on the rivers. 

Road trips from Chicago

Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.

Whether you’re taking the car out for an hour-long spin or you’re willing to buckle down for a few hours, you won’t be disappointed by the scenery along your journey or the fantastic destinations ahead. 

Related Posts:

• 7 Ways to Make the Most of Your Road Trip Budget
• Planning a Road Trip in the USA: 13 Best Routes!
• 57 Coolest Things to Do in Chicago for 2023
• Christmas Things to Do in Chicago in Winter: 21+…
• 14 Awesome Stops on a Chicago to New Orleans Road Trip
• 11 Unique Stops on the Drive from Chicago to Atlanta

Hi, I'm Vicky! I wrote this. You can find me on all the social media @VickyFlipFlop. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

One Comment

That’s no picture of Elkhart Lake

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

Sign me up for the newsletter!

9 easy must-do weekend trips from Chicago

Chicago is blessed with world-class museums, an amazing food scene, some of the best breweries in the country, and everything else you’d ever want to do. But even the most passionate Chicagoans need to escape the city every now and then. Luckily, there are dozens of superb weekend getaway destinations, all within a few hours’ drive of the Windy City. 

There are miles upon miles of Lake Michigan coastline to explore, there are national and state parks with gorgeous nature, and there are charming cities and towns all over the Great Lakes region where you can find a little bit of quaint comfort. Planning will go a long way to ensure a successful weekend trip. So research where to go, find luggage storage in Chicago if you need to drop the bags off, book lodging, plan where to eat and what to do, and hit the road. 

Here are the best weekend getaways from Chicago: 

Love discounts and traveling?

Sign up for our newsletter and get 10% off your next booking.

Dubuque, Iowa 

Located on the banks of the Mississippi River, Dubuque is the ideal weekend getaway for history buffs and older tourists. Baseball fans will want to visit the famous “ Field of Dreams ” ballpark, which is now the home of special events hosted by Major League Baseball. 

The town itself has been revitalized somewhat in recent years, with art galleries, breweries, murals, and restaurants opening in downtown Dubuque. Dubuque is heavy on the small-town charm and well worth a visit. 

Distance from Chicago 

It takes just under three hours to reach Dubuque from Chicago. Driving is the only option for transit. 

Our activity recommendations

This historic town is a delightful change from downtown Chicago, with a picturesque old-school Main street with many pre-Civil War buildings, like the Black Horse Inn. There’s also the Febekon Place Elevator, which is a scenic railway that overlooks the city and provides a spectacular aerial view. 

Best season to visit

Summer, fall, and spring are the best times of year to visit Dubuque. 

Holland, Michigan 

Western Michigan has a ton of delightful towns for weekend getaways, and Holland is one of the best family-friendly options. Located less than a mile from the stunning Lake Michigan coastline, Holland is famous for its large Dutch immigrant population and its furniture-making industry. 

Distance from Chicago

You’ll have to drive south and east for about two and a half hours to get to Holland. Driving really is the best way to get there, although Amtrak runs a train as well. 

Explore Holland’s (aptly-named) Dutch heritage by exploring delightfully kitschy attractions like Nelis’ Dutch Village, De Klomp Wooden Shoe, and the Windmill Island Gardens . 

In proper Dutch fashion, Holland (Michigan) celebrates the annual blooming of tulips every springtime. With millions of tulips planted across the area, it’s a gorgeous time of year to visit. Summer is also ideal, with the Lake Michigan shore and beaches only a mile away from town and gorgeous Lake Macatawa providing plenty of outdoor recreation. 

Grand Rapids, Michigan 

While far from the largest city in the country, Grand Rapids has a massive beer scene. Since the industry’s boom in the past two decades, Grand Rapids has quickly become one of the craft beer meccas, drawing thousands of beer nerds to its taprooms and breweries. 

It’s a three-hour drive from Chicago to Grand Rapids, probably less if you miss Friday traffic. Amtrak also runs a service from Union Station directly into downtown Grand Rapids, the train ride is about four hours. 

Beer truly is the main draw for visitors, with companies like Founders, Brewery Vivant, Saugatuck Brewing, and Grand Rapids Brewing all operating popular taprooms. The food isn’t bad at all either, with local favorites Forty Acres Soul Kitchen and Terra GR being high-end dining options.

When you’re not drinking, renting kayaks or bikes to enjoy the riverfront are great ways to stay active. Lake Michigan is less than 30 minutes away by car too.

Summer and fall are perfect for enjoying some time outdoors, especially if you’re looking at kayaking and swimming along the river or Lake Michigan. Winter is also a great time to do a long weekend because you can hit the slopes at the nearby Cannonsburg Ski Resort. Also, the many Grand Rapids breweries are great for a cozy pint to warm up.

Indiana Dunes National Park, Indiana

The sandy dunes overlooking Lake Michigan have finally gotten their due and were made into a national park. Indiana Dunes National Park is the closest conservation and recreation area of its kind to Chicago and the perfect weekend getaway (or day trip) for outdoor enthusiasts.  

It’s only about 90 minutes by car (which is the most convenient way to get there) from downtown Chicago. Unless you want to explore the whole area and stay in a cabin, Indiana Dunes National Park is one of the best day trips from Chicago. The South Shore Line will also take you to the Indiana Dunes, but driving is easier and more flexible. 

There are over 15 miles of beautiful Lake Michigan shoreline to explore and enjoy. You can enjoy the beach, go for a swim, hike the trails along the dunes, and even go horseback riding. 

Summer and fall are the best times to go. Visiting during winter is absolutely inadvisable because of lake effect weather. Spring is better, but the weather brings frequent rain that impacts the hiking trails and terrain.

Kohler, Wisconsin 

Located north of Milwaukee along Lake Michigan, Kohler is famous for its resorts and golf courses. The American Club is a bucket-list course for golfers, and there are a number of spas and restaurants that make Kohler a relaxing destination. 

Kohler is a two-and-a-half-hour drive from Chicago. A great way to break up the trip is to stop in Milwaukee for lunch.

Our activity recommendations 

The upscale resorts and golf courses are the main draw at Kohler, which makes them frequent weekend getaway destinations for older travelers. The Kohler Waters Spa is the perfect place to unwind, and the American Club boasts one of the best golf courses in the country. 

For weekend getaways based around golf, summer and fall are the best times of year to head up to Kohler. Kohler is also a wonderful destination for spas and resorts during the winter. 

Lake Geneva, Wisconsin 

Of all the weekend getaways from Chicago, this one has to be the most popular. Lake Geneva is Chicago’s equivalent of The Hamptons. Basically, everyone knows someone with a house up there. This makes sense, given it’s only a 90-minute drive from Chicago, just over the Wisconsin border. There are plenty of hotels, like The Abbey and Grand Geneva Resort . Multiple golf courses surround the lake as well. But the main reason to head to Lake Geneva is to appreciate the natural beauty with friends and family. 

Lake Geneva is about as close to Illinois as you get, and it only takes about 90 minutes to get there from Chicago by car, which is the only real way to get there. 

All the best activities in Lake Geneva are based around the water. Renting a boat from one of the marinas is a great way to get the family out on the water. There are multiple public beaches as well. 

During the winter, there is a village of ice castles made by expert sculptors that’s worth checking out. Alpine Valley Ski resort is nearby, which also hosts concerts during the summer. 

Summer is the best time to take a weekend trip to Lake Geneva, but it does get busy during this time of year. During the fall, Lake Geneva gets a boost when the leaves change color, despite it being too cold for boating and swimming. 

Madison, Wisconsin 

Wisconsin’s capital city is one of the most popular weekend getaways from Chicago. All the best Wisconsin culture is represented in Madison, which mostly consists of beer, brats, and Badger Football. The University of Wisconsin’s gorgeous campus is located right in Madison, which gives the city energy when students are on campus. But there’s a nice variety of outdoor activities and culture in the city as well. 

Madison is a three-hour drive from Chicago. There are also bus routes between downtown and Madison that take about three hours and 30 minutes. 

For such a small city, there’s plenty to do in Madison. Snowshoeing in the winter, hiking in the summer, appreciating the leaves in the fall, and drinking all year long. 

Just outside of Madison is the Wisconsin Dells area, which has indoor and outdoor water parks and other outdoor activities. It’s a great excursion from Madison and less than an hour’s drive from the capital. 

Summer and fall are the best times to visit, especially when the leaves change and the University is in full swing.

Milwaukee, Wisconsin

Chicago’s neighbor to the north is an obvious choice for weekend getaways. There is culture, there’s beer (and plenty of it), there are several pro sports teams, and there’s a lot of character. Milwaukee has all the amenities of a larger city, just without all the inconvenience of getting around a place like Chicago. 

If you’re driving up to Door County or Kohler, it’s well worth it to stop in Milwaukee for lunch. 

There is a train from Union Station that lands you right in downtown Milwaukee. This takes less than two hours and can save you some traffic headaches. The drive up to Beer City only takes about 90 minutes. 

There are a number of amazing museums to visit, including the Milwaukee Art Museum, which is a gorgeous modern building along the lakefront. There’s also the Harley Davidson museum which details the story of how Milwaukee became the largest builder of motorcycles in the world. 

Outside of that, there are world-class breweries, restaurants, and bars. Definitely make sure to try a famous Bloody Mary dressed up Wisconsin-style. 

The Milwaukee lakefront is incredible, and there are frequent festivals and events going on, so summer is an amazing time for a weekend trip. But there is enough culture that visiting Milwaukee is fun year-round. If you’re free during the first few weeks of July, hit up Milwaukee Summerfest , which is the largest music festival in the world. 

Starved Rock State Park, Illinois

As far as outdoor activities go, Chicago is hardly the best city in the world. But the area’s best hiking area is absolutely worth visiting. Starved Rock State Park, with waterfalls and topography (rare in a painfully flat state like Illinois), makes for a perfect weekend getaway for outdoorsy types.  

It’s only a two-hour drive from Chicago, but you’ll want to leave early to beat traffic and have a head start on the other hikers. Leaving yourself a full day to explore the nooks and crannies of this park is the best way to go. 

Essentially, there’s really only one thing to do at Starved Rock, and that’s hiking. With 13 miles of trails winding through glacier-carved canyons and terrain, it’s the best hiking Illinois has to offer. There are gorgeous waterfalls and winding streams to take a dip in if you’re hiking during the sweltering Illinois summer. 

Late spring, summer, and early fall are the best times of year to explore Starved Rock. Winter is basically out of the question. Early spring and late fall are entirely weather-dependent.

It’s hard for locals and transplants to find a place they love more than Chicago because there is a lot to love. But getting out of the city for a weekend getaway is a necessary way to recharge and reset. You’ll be more in tune with nature, you’ll feel a little more relaxed after taking a break from traffic, and you’ll have a new appreciation for the gorgeous region surrounding Chicago. If you’re short on time, you can always opt for a fun day trip from Chicago as well, and if you only have a limited time in the city itself, check out our guide on how to spend 3 days in Chicago to maximize your itinerary.

Planning one of the many fun weekend getaways from Chicago is a great way to find a new appreciation for not only the Midwest but also Chicago. Because you can only stay away from that deep dish for so long… 

Explore the world

Get the bounce app.

Instantly find locations nearby to drop off your luggage wherever you go.

• About Melissa
• _Charity & Small Biz Interviews
• -Chicago Suburbs Hiking

SOCIAL MEDIA

12 Super Road Trip Destinations from Chicago for Spring Break

Sunday, january 23, 2022.

12 Super Road Trip Destinations from Chicago Perfect for Your Next Adventure

With warmer days hopefully upon us soon, time is here to think about road trips! I am sharing a few of my favorites within a range of distances.  Happy trekking!

Within 3 Hours

Galena, Illinois: Downtown Galena enchants with one of the most beautiful historic districts in the USA. The bustling downtown full of shops, wineries, eateries and history beckons wanderers. Nearby hiking experiences are plentiful and treat to fantastic views of the Mississippi including from one of our favorites, Mississippi Palisades State Park . The Ulysses S. Grant is home is one of our favorites to tour and includes so many authentic family artifacts. While in Galena, wander over to nearby Dubuque, Iowa for a trip up the Fenelon Place Elevator. 

Madison, Wisconsin: Wisconsin's state capitol, Madison , unfolds an amazing opportunity for a family getaway. The Wisconsin State Capitol Building is striking and quite an interesting place to tour. Don't forget to step out on one of the balconies for a view. A plethora of hiking opportunities exist in and around the city including Lakeshore Nature Preserve, Blue Mound State Park, Devil's Staircase and Pheasant Branch Conservancy. Olbrich Botanical Gardens enchants in all seasons. Chazen Museum of Art, Madison Children's Museum and Wisconsin History Museum all add to any itinerary. We also love nibbling at the bakeries in Madison including Madison Sourdough and Batch Bakehouse. 

Quad Cities, Illinois and Iowa: The Quad Cities incorporates a number of Illinois and Iowa communities saddling the striking Mississippi River. A wealth of nature activities can be enjoyed including hiking and bird watching on Sylvan Island, at Black Hawk Historic Site, at Illiniwek Forest Preserve and more. Putnam Museum and Science Center, Figge Art Museum and Quad Cities Botanical Center offer more avenues of discovery. Don't forget to pick up ice cream at Whitey's or Lagomarcino's. For the over 21 crowd, hit the Quad Cities Ale Trail. We love the wealth of activities available and return to the Quad Cities again and again!

Within 6 Hours

Columbus, Ohio: Columbus has been one of our favorite cities to wander. We love German Village full of historic buildings and small businesses. Visiting Schmidt's Restaurant rewards with fabulous and authentic German fare. (My favorite is the German chocolate pie.) Museums include the Center of Science and Industry with a dinosaur gallery, Columbus Museum of Art and Central Ohio Fire Museum. We also enjoy visiting the Columbus Zoo and Aquarium which has one of the best African savanna experiences I have viewed.

Grand Rapids, Michigan:   Grand Rapids is home to one of my favorite botanical gardens and sculpture parks, Frederik Meijer Gardens & Sculpture Park. the grand scale sculptures are breathtaking and the gardens awe especially the Japanese garden. We also find the Grand Rapids Public Museum and Grand Rapids Art Museum fascinating. We usually pair a trip to Grand Rapids with a trip to Lake Michigan's shore often at Grand Haven. I am totally a beach lover in all seasons and often prefer spring for visits because there are fewer visitors. Rosy Mound Natural Trail in Grand Haven is one of our cherished nature highlights.

Hocking Hills, Ohio: Hocking Hills State Park in Ohio fascinates with a cache of unique hikes exploring canyons, caves, cliffs, waterfalls and much more. We love renting a cabin in the region for a little nature respite away from it all.

Louisville, Kentucky:   Louisville offers a great launching point for a Kentucky vacation. Museums including the Louisville Slugger Museum & Factory and Frazier History Museum present venues entertaining a range of interests. Churchill Downs is iconic. Louisville Mega Cavern bestows a venue for weaving through ropes courses and sliding along ziplines underground. The food scene includes so many of our favorites including Mark's Feed Store and Homemade Ice Cream and Pie Kitchen. The Camberly Brown and Seelbach hotels sweep you back to old hospitality. Of course, bourbon is a must for the 21+ crowd.

Shawnee National Forest: Shawnee National Forest in Southern Illinois welcomes travelers to unique hikes with unparalleled views. The forest includes a remarkable 289,000 acres of nature adventures to experience. Hiking, camping, horseback riding, biking, fishing, climbing, boating and more forge incredible nature experiences in some of the most unique settings of the Midwest.

St. Louis, Missouri:   St. Louis is an ideal location for a little getaway right along the mighty Mississippi River. The City Museum, St. Louis Science Center, St. Louis Zoo and St. Louis Art Museum among others inspire discovery. Of course, visitors must check out the Gateway Arch! Eating on 'The Hill' will treat you to fantastic Italian fare. You will also be near Cahokia Mounds where you can learn about the Mississippian Mound Builders. Additionally, you can head to St. Charles or Ste. Genevieve for a little French colonial history. When in St. Louis, one must also take an Anheuser-Busch Brewery Tour.  So many avenues of exploration make St. Louis a fabulous destination.

Within 8 Hours

Minneapolis and Saint Paul, Minnesota:   Minneapolis and Saint Paul have always been a favorite locale to visit. I love that there are spaces to admire nature right in Minneapolis and St. Paul including Minnehaha Falls, Chain of Lakes and Shadow Falls. Plus, there are tons of hiking opportunities nearby in Minnesota and Wisconsin. Mill City Museum and the Museum of Russian Art are two of my favorite museums in the Midwest. A walk along the Stone Arch Bridge and a peek at flour mill ruins provide an interesting look at Minneapolis. Como Zoo Conservatory in nearby Roseville treats to magnificent floral displays in all seasons. The region is populated with local microbrews adding tasting experiences.

Omaha, Nebraska: Perched along the Missouri River, Omaha offered us a wonderful starting point for a few nature adventures including Platte River State Park, Lewis and Clark Monument Park, Heron Haven and more. We loved walking around the Old Market, peeking into the Passageway and more. The city includes a wealth of museums such as the Durham Museum, Joslyn Art Museum, Omaha Children's Museum present a wealth of adventures.  For a truly unique scene, visit Hollywood Candy which not only delights with tons and tons of candy but includes a vintage pinball arcade, movie memorabilia, a '50s diner, vinyls and so much more!

Pittsburgh, Pennsylvania: Pittsburgh is a fantastic vacation choice for any season. The city's range of museums inspires any wanderer. The National Aviary is a wonder that should not be missed. Several rooms are free-fly, so you will have all sorts of interesting birds freely flying and roaming. Andy Warhol Museum, Heinz History Center, Carnegie Museum of Natural History and more will invite exploration. Don't forget to take the Duquesne Incline up to the top of Mount Washington for a view. We have to take in this view EVERY time we are in the city. Wander the Strip District for all sorts of foodie treats and shops. Hiking, river views and more will entice nature lovers. Every trip to Pittsburgh welcomes us to new experiences.

Post a Comment

15 Best Winter Road Trips from Chicago

Chicago is a fantastic city, known for its stunning lakeside location, the Magnificent Mile, and its world-class museums and galleries. However, it's also famous for its harsh winters, so there might be times you want to head out of the city during the coldest months of the year.

Whether you want to enjoy the winter weather or escape from it, a winter road trip from Chicago can mean hitting the slopes at a ski resort, viewing iconic landmarks, taking a festive shopping trip or relaxing in the winter sun in the Southern states.

Whatever kind of winter road trip you're interested in, we've put together some of the key facts for a whole host of fabulous destinations. Keep reading to find out where you could go, how to get there, and our pick of what's waiting for you when you arrive.

Best winter road trips from Chicago: a quick overview

Single-day trips (under 3 hours each way).

Snow in the city often isn't much fun, so head out to one of the mountains or lakes for a one-day road trip that lets you enjoy the winter weather at its best.

If you're thinking of setting off on a road trip from Chicago in another season, check out our ultimate guide for Best Road Trips from Chicago for ideas and inspiration.

1. Lake Geneva, Wisconsin

1 hour 50 mins from Chicago (80 miles)

Why you should visit: The shortest trip on the list, Lake Geneva makes a great weekend getaway due to the short driving time, plus the area is perfectly set up for visitors to enjoy the winter weather.

There's a real variety of activities to enjoy here – take to the snow for an active day outside, then relax at a beautiful spa. This popular vacation town is also less crowded in winter compared to the summer months.

How to get there: Head north on I-90 out of Chicago then join I-94. After around an hour, exit at Kenosha and pick up WI-50 west which will take you to Geneva.

Our highlights: Roll back 100 years and one of the biggest draws of Lake Geneva, WI, wasn't its snow, but the ice! Lake ice was harvested and taken to nearby towns and cities - it was big business here as late as the 1940s.

Through the rest of the season, winter sports fans will love to ski at Wilmot Mountain, a popular ski resort with over 20 ski runs suitable for a wide range of abilities. Or explore the wintery wilderness of Kishwauketoe Nature Conservancy - you can rent snowshoes if you don't have your own.

Back in town, the Ice Castles at Geneva National Resort & Club are a must-see. Ice sculptors spend nearly 2 months creating spectacular icy towers and turrets which are especially beautiful when they're illuminated at night.

Bonus: Early in February Lake Geneva's Winterfest bursts into action, with an ice sculpting competition and snow races!

Our travel tips: Book in advance if you're visiting Winterfest, as the town gets really busy.

2. Madison, Wisconsin

2 hours 40 minutes from Chicago (150 miles)

Why you should visit: Wisconsin's state capital has all the cultural and foodie delights that you'd expect in a big city, with added snow that opens up a whole range of other activities to enjoy.

Within a short distance of the city you can ski, skate, snow tube and sled, sometimes with beautiful views across Lake Mendota.

How to get there: This is a really simple trip – just follow I-90 all the way from Chicago.

Our highlights: Just outside the city at Cascade Mountain and Devils Head Resort you'll find some exhilarating downhill skiing as well as snowtubing and sledding. It's the perfect way to enjoy the snowy conditions, and there are ski runs here to suit many different abilities.

When it's time to warm up, head back into town to Old Sugar Distillery, a small local spirits producer, for a warming taster.

While you're in town you can take a magical snowy hike through the trees at Madison Arboretum, then round off your day with outdoor dining - several Madison restaurants have heated outdoor domes so you can enjoy snowy views while dining al fresco.

Bonus: After Christmas, a free maze is built on the lake shore out of the branches of discarded Christmas trees, a custom that has become firmly cemented in Madison's holiday traditions now.

Our travel tips: Check ahead for dates of candle-lit snowshoe trails across the city. They don't run every day, but when they do they're really magical.

3. Elkhart Lake, Wisconsin

2 hours 50 minutes from Chicago (150 miles)

Why you should visit: This beautiful little lakeside town hosts a magical Christmas market every year. It's also a great place to enjoy fabulous snow-based activities - the temperature usually sits around freezing and the area experiences heavy snowfall, so conditions are perfect.

How to get there: Follow I-90/I-94 north out of Chicago, then continue north on I-94 when the interstate divides. In Milwaukee, switch onto I-43 and continue north, before leaving the interstate just after Saukville. Then, follow WI-57 towards Plymouth, from where you'll pick up WI-67 to Elkhart Lake.

Our highlights: For many visitors, the main draw is the Olde World Christmas Market, a 10-day festive spectacular bringing together Czech, German and Russian Christmas traditions. It's a great way to spend time with friends, get into the festive mood, as well as to find some unique Christmas gifts.

If you're visiting at other times during the winter, there's still plenty to do in Elkhart Lake. The lake freezes over right through the winter, so you can head out with a guide for a unique ice-fishing experience.

Also, although this isn't a ski destination like some of the other trips, you can still enjoy some winter sports in Elkhart Lake. Go snowshoeing at Quit Qui Oc golf course or ice skate at June Vollrath Park.

Alternatively, if you'd prefer to just relax and unwind, maybe after a tour round the Christmas market or some time on the ice rink, head to the luxurious Aspira Spa to round off your trip.

If you're wondering how the town got its name, it's as simple as it sounds – it's because the lake is shaped like an Elk's heart.

Our travel tips: The town will be extremely busy while the Christmas market is running, so book accommodation and any special activities well in advance.

4. Grand Rapids, Michigan

2 hours 50 minutes from Chicago (180 miles)

Why you should visit: From January to March the town hosts the World of Winter Festival, which sees dozens of huge ice sculptures on display and special events held across the town.

The World of Winter Festival is the perfect post-holiday pick-me-up - the ideal way to brighten up the dark, cold months after Christmas. Or if you're here a little earlier in winter, you can get yourself into the holiday spirit with a snowy visit to the Sculpture Gardens or enjoy some exhilarating winter sports.

How to get there: Head east out of Chicago on I-90, keeping Lake Michigan on your left, then continue on I-94 as far as Lake Joseph. From here, follow I-196 further around the lake shore. It eventually turns inland to take you right to Grand Rapids.

Our highlights: The World of Winter Festival usually starts in the first week of January, and as well as ice sculptures you can see interactive installations from artists all over the world, with walking tours taking you through some of the outdoor art highlights.

The festival also hosts many fun events. These change year on year, but in the past have included things like silent disco, outdoor musical performances, and storytelling to mark Native American traditions or Chinese New Year.

If you're in Grand Rapids earlier in the season, you can enjoy some great skiing at Cannonsburg Ski Area. It will satisfy a wide range of abilities, and you can also try out snow tubing and snowshoeing here.

If your time is limited, take your sled and enjoy a free downhill ride at one of the several hilly public parks in the city.

For a more magical festive feel, head to Frederick Meijer Sculpture Gardens. This park is illuminated with amazing twinkling lights all through the holiday period and is a really popular local attraction. Then, for a unique and romantic end to your trip, you can even take a horse-drawn sleigh ride through the city.

Bonus: As well as being known for its winter sports, Grand Rapids is famous for its many craft breweries - in fact, it's been given the title of Beer City USA! So if time allows on your trip, you might like to tour a brewery or two or try some of the locally produced beers.

Our travel tips: You don't have to have your own equipment to enjoy skating, snowshoeing or skiing – it's available to rent at many of the attractions.

If you're coming for the World of Winter Festival, remember to wrap up warm. Many of the events and installations are outdoors, so, this being Michigan, chances are you'll be enjoying them in the snow.

Click here to skip back to the top.

Weekend trips (3-6 hours each way)

As you'd expect, with much of the Midwest sitting under snow through the winter, the weekend trips you can take from Chicago all have a winter sports element to them.

So, pack up your skis and look out for your skates - but don't worry if you're not the biggest fan of the slopes, since you'll also find great restaurants, beautiful views and stunning spas at these weekend destinations.

5. Muskegon, Michigan

3 hours 20 minutes from Chicago (190 miles)

Why you should visit: As you'd expect in a town that sees significant snowfall from December to February, you can enjoy a range of winter sports. A particular highlight in Muskegon is its Luge track, which is open to the public.

There are only 3 other Luge tracks in the whole of the United States, so if you've always fancied trying out this exhilarating sport, this is probably your best chance.

How to get there: Similar to the Grand Rapids trip, follow I-90 then I-94 east out of Chicago as far as St Joseph. Then join I-196 and follow it north along the lake shore until you reach Holland. From here, turn onto Route 31 which takes you on to Muskegon.

Our highlights: As you'd expect, the main draw of Muskegon in winter is Muskegon Luge Adventure Sports Park. As well as sliding the high-speed downhill ice track, you can enjoy cross-country and downhill skiing, snowshoeing, and ice skating at the park.

Back in town you'll get beautiful winter views over icy Lake Michigan. Wrap up warm and walk out towards Muskegon South Breakwater Lighthouse – a really stunning sight – or take a walk on the lake's frozen beaches. If you're feeling active, there are places where you can sled on the frozen sand dunes.

Staying by the lake, seeing as the water freezes over, you can go ice fishing here with a guide, who can provide all the equipment you need if you don't have your own.

It's not all about the outdoors though. Muskegon Farmers Market operates indoors on Saturdays through the winter so you can warm up and stock up on some fabulous local produce.

Olympian Mark Grimmette trained on the Luge track here when he was young and went on to compete at five Winter Olympic Games, winning medals at two of them. The track is open to kids as young as 8 so bring the whole family and see if any of them catch the sliding bug.

Our travel tips: Visit the Luge in the evenings and you can warm up by a bonfire after your slide down the track. We'd recommend booking ahead to guarantee your entry, especially if you're visiting at busy times,.

You won't need any previous experience or equipment, as your entrance to the track includes a lesson and all the equipment you'll need to enjoy your visit safely.

6. Granite Peak Ski Area, Wisconsin

4 hours 30 minutes from Chicago (280 miles)

Why you should visit: As its name suggests, Granite Peak is a fabulous and long-established ski destination with some top-class runs and luxurious resort choices.

The biggest ski area in the state is perfectly set up for skiers, with fast lifts and dozens of trails to follow. You can easily fill a weekend here with fun and varied runs.

How to get there: Follow I-90 west out of Chicago, passing Rockford and Madison. Then, shortly after crossing the Wisconsin River, turn onto I-39 and follow it north to Granite Peak Ski Area.

Our highlights: Granite Mountain is one of the oldest ski resorts in the United States, and it's been at the forefront of innovation in the skiing industry. It was an early adopter of snowmaking technology in the 1950s.

Two different types of ski lifts were invented here - so when you ski here in modern times you'll be following the lead of some of the country's ski pioneers.

With fast lifts, extensive ski runs and stunning views, you'll probably want to spend most of your time here on the slopes. Rib Mountain, part of the ski area here, is Wisconsin's tallest mountain so you'll find plenty of downhill runs here to suit all abilities.

In Wasau, the nearest town to Granite Peak, there are some great food and drink options for the essential apres-ski part of the day! Visit in early February when the Winter Carnival comes to town and you can see firework displays or catch a fun ride on one of the resort's snow groomers.

When you're ready to head into the warm, make your way to Leigh Yawkey Woodson Art Museum. This award-winning, community-focused gallery always has something new to see, and with sculptures and exhibits inspired by nature, it makes the perfect complement to a day enjoying the views out on the mountain.

Our travel tips: This is a really popular ski area, and lift passes can sell out during the busiest periods. It makes sense to book ahead if you're planning on visiting between Christmas day and New Year, or weekends during January and February.

7. Boyne Mountain Resort, Michigan

5 hours 40 minutes from Chicago (350 miles)

Why you should visit: This is a year-round resort, but with 140 inches of snow, it comes into its own during winter. The extensive and varied ski slopes here are great for a wide range of skiing abilities.

This is the place to come for a great resort experience, with lodges, bars and of course, slopes, all in one place.

How to get there: Follow the interstate east out of Chicago and then continue north, keeping Lake Michigan on your left. After Grand Rapids, turn onto Route 131 and continue north past Big Rapids and Cadillac, until you reach Boyne Mountain.

Our highlights: Boyne Mountain is primarily a ski resort, so take to the slopes and explore more than 415 acres of ski runs. You can also snowshoe, tube or skate if you want a break from the slopes.

If you want to strike out a little further and explore, you can go horseback riding or cross-country skiing through the woodlands or try out snow biking for something new.

For a really exhilarating ride, fly right above the snow on one of the 9 ziplines. These will carry you up to a quarter of a mile across the resort's valleys, giving you a bird's eye view of your stunning surroundings.

For the perfect post-ski wind down, visit the Spa at Boyne Mountain before you head home. Book a fantastic treatment or simply hang out in the sauna, steam room or heated outdoor pool to enjoy the mountain vibes from a different angle.

Our travel tips: Equipment can be rented at this resort but arrive early on weekends or holidays as it's first come, first served. It's a popular place to visit, so book lift passes in advance if you know when you're traveling. If you're able to visit mid-week, you'll probably find the slopes are quieter.

Longer trips (Over 6 hours each way)

Whether you're looking for a festive shopping experience to ease you into the holiday mood, or a snowbird heading south for the winter, there are plenty of fabulous longer road trips that start out from Chicago.

8. Niagara Falls and Niagara-on-the-Lake, New York

8 hours 20 minutes from Chicago (550 miles)

Why you should visit: Seeing the famous falls cascading through the snowy ground is a truly magical experience – and one that's different from any other trip you might take.

Head across the border on this road trip to see the falls from a different perspective, or visit the fabulous wineries of Niagara-on-the-Lake. Canada produces a significant proportion of the world's Icewine, a dessert wine created from grapes left on the vine to freeze before being harvested.

Seeing the falls in winter is a magical experience, with massive icicles and undulating snow drifts surrounding the famous vistas. As well as being beautiful, the crowds that flock to Niagara Falls are slightly less during winter.

How to get there: Head east out of Chicago and join Interstate 90, then just keep going! The same road takes you right across Indiana and Ohio then along the whole length of Lake Erie, before you finally turn onto NY-5 through Buffalo around 5 miles before you reach your destination.

If you want to head across the border to visit Niagara-on-the-Lake make sure to pack the required travel documentation, and allow extra time to make the border crossing, especially if you're heading across Rainbow International Bridge.

Our highlights: The highlight of most people's visit to Niagara Falls is to see the mighty waterfalls up close, but if you visit in winter you can also marvel at the massive icicles that form right by the viewing platform on the Journey Behind the Falls. For amazing views of the snow-covered landscape, head up the Skylon Tower.

At night, you can see the falls lit up in spectacular illuminations as part of the Winter Festival of Lights. Then head quickly back into the warmth of your hotel to warm up. Several of the hotels in town have excellent in-house spas, so you can treat yourself to some relaxation time during your trip.

If you're crossing over the Canadian border to visit Niagara-on-the-Lake, the Icewine vineyards and wineries are probably the first thing that will get your attention. The long rows of vines stand out proudly in the snow and make a beautiful backdrop while you're learning about Icewine production or, more importantly, tasting a glass or two.

NOTL is also a really charming little town, and while you're here you might like to take a horse-drawn carriage ride through its historic streets - a wonderfully atmospheric way to travel through the snow-covered streets.

Bonus: Right through January you can enjoy the Icewine Festival, which celebrates this delicious local tipple. There's a real art to making Icewine and the conditions have to be just right to freeze the grapes for long enough on the vine.

This means you probably won't see the grape harvest unless you're out in the vineyards at night - pickers tend to work by hand to make sure of the most perfect harvest possible. All things considered, it's easy to see why Niagara-on-the-Lake's Icewine is such a special product to try during your visit.

Our travel tips: Some of the outdoor activities that Niagara Falls is famous for, notably the Maid of the Mist boat cruise, do not operate in winter, but as we've identified, there are plenty of other ways to enjoy views out across the falls.

Note that to enjoy all the attractions Niagara Falls has to offer, you might need to factor in crossing the US/Canada border so make sure you have any paperwork you need (dependent on nationality).

READ MORE - Road Trip from Chicago to Niagara Falls

9. Toronto, Canada

8 hours 40 minutes from Chicago (530 miles)

Why you should visit: With festive lights, winter markets, a good chance of snow, and plenty of big city attractions, Toronto is a picture-perfect winter city trip . Located right by Lake Ontario, you can enjoy frosty views out across the water, then head back into the city to indulge yourself in some culture or plain old festive cheer.

It's the perfect place for a romantic getaway - wrap up warm and enjoy snowy views over the beautiful city and lake before warming up with a hot chocolate and a loop or two around an outdoor ice rink.

How to get there: Follow I-90 out of the city then pick up I-94 and head east towards Detroit.

After crossing the border into Canada, the road becomes ON-401. It runs parallel to Lake Erie, so if you have a little longer to make your trip then you might like to pause along the way to admire views across the lake.

Just after London, the road merges with ON-403, which will take you right into the center of Toronto.

Our highlights: Toronto is a vibrant cultural melting pot, so when you spend time in the city you'll be able to enjoy influences on food, art and recreation from all over the world.

Less than half of Toronto's residents were born in Canada, making for a varied and welcoming city that's the perfect place to head to on a road trip.

For added romantic charm, put your skates on and have laps on one of the city's many ice rinks - there are over 50 to choose from. The rinks are super-festive in the run up to the holidays, and you can relax with a hot chocolate or a local craft beer afterwards.

If you're not planning a trip until after Christmas, you'll be able to visit the Toronto Light Festival, when fabulous installations brighten up the city through the cold winter nights. Check ahead to find details of live performances and special events that are taking place.

If it's your first time in Toronto, you'll probably want to see some of the city's sights while you're in town too. Head up the CN Tower for great views of the city and Lake Ontario, which is particularly stunning when it starts to freeze over through the winter.

Then warm up in one of the city's fantastic museums, including the Royal Ontario Museum where you'll find a fascinating and diverse collection.

Bonus: If you're here before the holidays, get into the festive spirit at the Distillery District Christmas Market, which runs from mid-November until New Year. It's a great way to experience this historic part of the city, full of character.

Our travel tips: Although temperatures are at or below freezing through most of the winter, you're not always guaranteed snow in Toronto, so be prepared that you might miss out on the insta-perfect images of this particular winter road trip.

As you can see, there are still plenty of wintery attractions to enjoy in the city, just wrap up warm and see where your trip takes you.

READ MORE - Road Trip from Chicago to Toronto

10. Washington, DC

11 hours 10 minutes from Chicago (700 miles)

Why you should visit: You can see the Nation's Christmas Tree, a century-old tradition in the city - it's illuminated from early December in a popular ceremony that for many marks the start of the holiday season.

You can also enjoy a number of holiday markets, to really get you into the festive spirit. You have a few to choose from, including the outdoor Downtown DC Holiday Market, the Swedish Christmas Bazaar in Georgetown, and the Heurich House Museum Christkindlmarkt.

As well as all the holiday attractions and the chance to see some of the world-famous monuments beautifully surrounded by snow, the crowds at the city's museums are likely to be quieter during the winter.

How to get there: Follow I-90 out of Chicago and east towards Cleveland. Then, join I-80 and follow it around the south of Cleveland before switching onto I-76 and continuing southeast past Pittsburgh.

After passing New Baltimore and Everett, change onto I-70 and continue on through the Appalachians before joining I-270 at Frederick and following it right into the center of Washington DC.

Our highlights: The nation's capital is a fantastic place to visit during the holiday period. As well as the festive markets that take place across the city, where you can admire beautiful decorations and gifts or enjoy some fabulous food and drink, you can take in a carol concert at the National Cathedral.

Afterwards, take some time to admire the cathedral's architecture - and see if you can spot the Darth Vader gargoyle.

Back outdoors, visit DC's largest outdoor ice rink at Washington Harbor, for views out across the waterfront, or see the Holiday Boat Parade, which includes fireworks and live music as well as festively decorated boats parading down the Potomac River.

If you're visiting later in the season, check out Winter Restaurant Week. The event runs in late Jan or early Feb, and hundreds of the city's restaurants showcase their best meals at reasonable prices - the perfect way to brighten up a long, cold winter.

Don't forget to check out some of the Smithsonian museums too – they're free to enter so you can visit one or many, and enjoy some of the more popular sites without the crowds, especially if you're visiting after the holiday period.

Bonus: The capital hosts a fabulous Lunar New Year Parade in January or February depending on when the new year begins. The parade brings together dragons and lions dancing through DC's streets, as well as drummers, dance troupes and firecrackers - it's a real feast for the senses.

Our travel tips: Don't go to DC expecting reliable snowfall – daytime temperatures are milder than the more northern destinations (in the mid-40 degrees Fahrenheit and above), though it still gets pretty cold at night, and snow is likely but not guaranteed in January and February.

The key message is to wrap up warm and be prepared for whatever weather the city throws at you - pretty standard for DC!

READ MORE - Road Trip from Chicago to Washington DC

11. Philadelphia, Pennsylvania

11 hours 50 minutes from Chicago (760 miles)

Why you should visit: Pennsylvania combines the kind of winter fun you might expect, like sledding and skating, with some unique winter traditions.

Visitors and locals alike flock to the Macy's Light Show, running for over half a century, and the charming Dickens Village, also found at the store.

Plus, you can fill yourself with festive cheer with a visit to the traditional market at Love Park's Christmas Village, or a stroll through streets filled with fabulous Christmas lights.

How to get there: Follow I-90 east towards Cleveland, switching onto I-80 just before you reach the city. This leads you south to join I-76, which you'll then follow past Pittsburgh, all the way across Pennsylvania. The same road takes you right into Philadelphia

Our highlights: You can see all the historic gems of Philly decked out with lights and trees for the holiday season, and the city's beautiful riverside setting just adds to the magic.

As you make your way from Chicago to Philadelphia , make sure to fit in a visit to Bethlehem, PA, too. The whole town gets decked out in style for the holidays. Take a magical horse-drawn carriage ride, check out entries for the Gingerbread House competition, and enjoy endless festive lights.

Once you've arrived in Philadelphia, you can ice skate beside the Delaware River at Winterfest, then warm up with a hot chocolate - or something stronger - with a view out across Benjamin Franklin Bridge.

Then, check out the Christmas Village or the Made in Philadelphia Holiday Market. If you're looking for unique and often hand-made gifts for family and friends, you'll find plenty of choice here.

The city's popular Longwood Gardens is transformed with amazing lights and live music, so it makes a great place to spend some time after the sun goes down (which happens early in winter!)

If you're in Philadelphia towards the end of the holiday season, you'll be able to watch the Mummers' Parade on New Year's Day. Thousands of people in absolutely dazzling costumes parade through the city in a historic tradition.

Bonus: Macy's Christmas Light Show – another of the city's festive traditions – is a record breaker! It features more than 100,000 lights and is the largest pipe organ in the world.

Our travel tips: Timed tickets are needed for some of Philadelphia's winter attractions, including Longwood Gardens and Dickens Village.

READ MORE - Road Trip from Chicago to Philadelphia

12. New York, NY

12 hours 40 minutes from Chicago (800 miles)

Why you should visit: New York City puts on an amazing holiday display – from festive lights to Christmas trees and fabulous window displays throughout the city, all with a thick covering of snow. This road trip from Chicago to New York is truly nothing short of magical!

Plus, if you're in the market for some Christmas shopping you can take your pick of fabulous department stores, designer brands and boutique sellers.

Get into the festive spirit and enjoy the iconic holiday views of the city - if it feels familiar, it's probably because they've featured in so many films and TV shows over the years. You should definitely visit New York in winter so you can say you've experienced them all first-hand.

How to get there: Follow I-90 east across Indiana. Just before Cleveland, merge onto I-80 and follow this all the way across Ohio, Pennsylvania and New Jersey before crossing into Manhattan via George Washington Bridge.

Our highlights: There are so many memorable festive moments to fit into a winter trip to New York City that it's hard to know where to begin. Skate beneath the massive Christmas tree at the famous Rockefeller Ice Rink, before heading up to the Top of the Rock to take in the view of New York in the snow.

Take a carriage ride through Central Park, which is even more magical when there's snow on the ground. Or if you're feeling more active, there are sledding slopes in the park, too.

Of course, NYC is famous for its shops, so leave some space in your case for whatever gifts and treats you might pick up while you're in town. Head to Macy's, Bloomingdale's or Saks Fifth Avenue for wall-to-wall shopping opportunities, or take a walk along Fifth Avenue to indulge in designer brands.

Further afield, the city is packed full of other shopping districts, including the West Village, Bleeker Street, Union Square and the Meatpacking District to name just a few. Or if you're in town with romantic intentions, a stroll through the Diamond District might go down well.

For a different experience of New York in winter, skip the crowds and visit in January to enjoy the NYC Winter Jazz Fest or NYC Restaurant Week, where restaurants put on their best fare at affordable prices.

If you're traveling at this time of the year, you can also stop off at New Hope, PA, as you make your way from Chicago to New York City. Here you can join in with the 9-day Winter Festival (late January).

Galleries, restaurants, and local businesses come together to bring some warmth and cheer to the new year, with a legendary chili cook-off, Soup-A-Thon, and ice sculptures dotted around town.

Bonus: These days, you usually need to take a ferry across from Manhattan to Staten Island, but back in 1780, the entire harbor froze so hard that it was possible to walk all the way across the river.

Our travel tips: Parts of the city get extremely crowded in December, and accommodation prices rise accordingly. The first week of December is particularly busy, but many travelers report that the crowds and prices calm down a little mid-month.

If you'd like to learn more about the best areas to stay in NYC before you plan your trip, you can find our detailed area-by-area guide here .

READ MORE - Road Trip from Chicago to New York City

13. New Orleans, Louisiana

13 hours 40 minutes from Chicago (925 miles)

Why you should visit: Mild weather and weeks of flamboyant parades makes New Orleans the perfect contrast to snowy Chicago. The city is famous for Mardi Gras, which takes place in late February, but warm-up events actually start in January, so you can enjoy week after week of enjoyment.

As well as Mardi Gras, New Orleans is also a vibrant city where you can enjoy live music, fabulous food and warm winter weather - perhaps the closest you can get to a trip overseas without needing a passport!

How to get there: On this road trip , join I-57 and follow it south all the way to Cairo, on the Illinois/Missouri border. Then, soon after crossing the Mississippi River, change onto I-55 and follow it south.

As far as Nashville, I-55 runs parallel to the Mississippi before passing through Jackson. Continue along the interstate then, after skirting the west side of Lake Pontchartrain, merge onto I-10, which takes you into the center of New Orleans.

Our highlights: From Thanksgiving onwards, enjoy a Reveillon Dinner – a local tradition that now sees restaurants across the city offering seasonal Creole-inspired food all through December.

Also running from Thanksgiving right up to New Year's Day is Celebration in the Oaks. This after-dark spectacle sees City Park lit up with more than a million lights. Given the city's mild winter climate, it's the perfect place to end the day with a romantic stroll.

If you're in the city for Christmas itself, head out along River Road on Christmas Eve, where you'll see bonfires lit on the night of the 24th so that Papa Noel can find his way from Baton Rouge to New Orleans.

Once Christmas and New Year are behind you, the party season in New Orleans really gets going. From mid-January, you can see parades and events starting up, then the main event, Mardi Gras, starts on Shrove Tuesday and carries on for two weeks. Expect fabulous parades, live music and all-night parties.

You'll have seen pictures of the beautiful and elaborate masks that are such a feature of the Mardi Gras parades. But did you know that every single participant has to wear one?

That way, current and future visitors will be guaranteed the same fabulous experience of NOLA's longstanding and unique traditions.

Our travel tips: Although average temperatures sit around 60 degrees Fahrenheit in winter, they can drop much lower or rise as high as 80, so it's wise to pack for three seasons to be prepared for a winter trip here!

READ MORE - Road Trip from Chicago to New Orleans

14. Savannah, Georgia

15 hours 10 minutes from Chicago (960 miles)

Why you should visit: The weather stays mild all year round in Savannah, so it's a great place to come and escape the Midwest chill. You can enjoy spending time outside, take a walk along the river, or just relax in one of Savannah's beautiful squares - the polar opposite of a Chicago winter.

Don't worry about missing out on too much of that winter snow either - your drive will take you through the Appalachians so you can take in some stunning views as you make your way south to Georgia.

Savannah is a great place to visit all year round but come in winter to enjoy this fabulous city without the summer crowds or humidity.

How to get there: After heading east out of Chicago on I-90, turn south onto I-65 and continue through Indianapolis and Louisville.

At Louisville, change onto I-64 and follow it towards Lexington onto I-75 which takes you across into Tennessee. Then, take I-40 from Knoxville to Asheville then join I-26 south passing Spartanburg and Columbia.

This leads you eventually onto I-95, which you'll follow south to Savannah.

Our highlights: There might not be snow and ice on the ground, but Savannah manages to fill the holiday season with its very own brand of festive charm.

At Coastal Georgia Botanical Gardens, you can follow the beautiful light trail through the magical gardens, for example, or take a holiday trolley tour or boat trip to see the city decked out in festive finery while enjoying a wonderful warm cider.

Then, follow the Christmas Parade, which makes its way through the city's streets and squares in early December.

All through the winter, you can also enjoy the shops and restaurants on fabulous River Street, the perfect place to spend some time whether you're looking for gifts to take home or just something special for yourself.

The city was offered up to President Lincoln as a Christmas Gift during the Civil War. As Christmas gifts go, a whole city is one we wouldn't mind receiving!

Our travel tips: Winter weather in Savannah is changeable, but the year-round humidity can make even warm days feel chilly when you're outdoors for a while.

READ MORE - Road Trip from Chicago to Savannah

15. Orlando, Florida

17 hours 30 minutes from Chicago (1,130 miles)

Why you should visit: Orlando is known as a winter sun favorite – so pack your sun cream and enjoy some time outdoors.

The theme parks of Orlando are popular year-round, but during the winter you get to experience them all dressed up for the holiday season, and without the heat and humidity that can be a feature at other times of the year.

How to get there: Follow I-90 out of Chicago then merge onto US-41 at the southern tip of Lake Michigan and continue south past Terre Haute and Vincennes.

Just after crossing the Ohio River at Evansville, turn onto I-69, continuing south on I-169 where the interstates divide. After Hopkinsville, join I-24 and follow it through Nashville to Chattanooga, where you'll switch onto I-75 which runs all the way to Florida.

After Gainesville, join the Florida Turnpike which takes you the last stretch of the drive into Orlando.

Our highlights: Florida is the warmest part of the continental US through the winter - perfect for escaping the sub-zero temperatures of the Midwest on this road trip from Chicago to Orlando !

Visit the theme parks in their holiday finest – whether your first choice is Walt Disney World, Universal Orlando, SeaWorld or Legoland Florida, each one will be suitably festive with parades and events to match.

You can see Cinderella's Castle made even more magical at Walt Disney World, or visit EPCOT's International Festival of the Holidays to take a whistle-stop tour around the world's traditions.

One that stands out for its festive themes is the Grinch-mas Who-liday Special at Universal Islands of Adventure. And of course, the Wizarding World of Harry Potter comes into its own during the winter.

If you have time to head out of town, make your way to Tampa to see Christmas Town at Busch Gardens. You'll find yourself in a warm weather wonderland with trees, lights, skating and fireworks.

Outside of the theme parks, you can enjoy the Winter Park Christmas Parade, a long-standing Florida tradition, with dozens of troupes followed by Santa.

And if you're missing that traditional winter vibe, visit Now Snowing in Celebration, where frosty views meet the Florida sun – including hourly snow flurries.

Our travel tips: Pack layers, as even Florida can experience cooler days, but rest assured that with heated pools and plenty of daytime sunshine, you can enjoy yourself outdoors right through the winter.

READ MORE - Road Trip from Chicago to Orlando

Join our email list!

By joining our email list, you give LazyTrips permission to use your email for sending you newsletters, emails and updates including for marketing purposes. Your email will not be provided to third parties.

Related posts

14 Things To Do In Rockford: Complete Guide To The Illinois City Just Outside Chicago

L ocated to the north of the state of Illinois, the Midwestern city of Rockford offers a less crowded holiday destination compared to Chicago . Rockford is the seat of Winnebago County and is perched on the banks of Rockford River. This geographic advantage further elevates the touristic quality of the city, providing scenic waterfront attractions to explore. In addition, the city is renowned for its forests, symbolic and scenic gardens, arboretums, parks, as well as museums that preserve fascinating history.

For visitors with a love for unique or vintage architecture, Rockford offers a number of interesting attractions, among them the Tinker Swiss Cottage. The growth of the city’s tourism sector is impacted by its proximity to Chicago, particularly as travelers consistently seek more non-traditional tourism locations.

Gradually stamping its profile as a worthy, non-traditional travel destination in Illinois like Chesterfield , Rockford offers diverse attractions and activities ideal for both solo travelers and family groups.

UPDATE: 2023/08/03 08:56 EST BY BARRY JUMA

An Expanded List Of Things To Do In Rockford, Illinois

Although Rockford may not elicit as much excitement as its larger Illinois counterpart Chicago, it certainly has a number of attractions that are bound to keep visitors busy. This expanded list includes some options within a short drive from the city, including the scenic White Pines Forest State Park and Rock Cut State Park, with the latter located just 10 miles from Rockford.

Top Things To Do

From discovering and savoring diverse nature to getting in touch with Rockford’s history and heritage, there is no shortage of things to do in the city.

Visit The Klehm Arboretum And Botanic Garden

The garden and arboretum offer 155 acres of unique gardens and fountains with sculptures, creating picturesque and tranquil spots for sightseeing and outdoor relaxation. One may also opt to hike along the cleared hiking trails or try out the forest routes.

The arboretum has some rare, unique trees including a variety of maple, oak, pine, elm, spruce, and fir species from Europe, Asia, and North America. One of its highlights is a bur oak grove with trees as old as 300 years.

One has several gardens to explore, with popular ones including the daylily, children’s, pre-historic, and butterfly gardens.

• Address: 2715 S Main St, Rockford, IL 61102
• Hours: Daily from 9 am to 4 pm

The last batch of visitors is allowed entry at 3:30 pm

Head To The Famed Anderson Japanese Gardens And Laurent House

This is among the most visited attractions in Rockford, and it features numerous, diverse species of flora and fauna. Aside from plant species like magnolias and azaleas, the gardens also have ponds, cascading waterfalls, streams, rocks, and a Japanese-style teahouse.

The 12-acre park showcases nature, but there are a number of wellness services offered within the gardens including yoga classes, gong baths, tai chi, and meditation. Visitors can also opt to sample the fascinating cultural and educational events hosted at the gardens.

To grab a bite, head to Fresco, which is within the gardens. There is also a gift shop onsite.

For a more in-depth exploration of the gardens, visitors have the option of private or public tours. These tours include a stop at the Sukiya-style guest house with its marvelous post and beam construction style and Laurent House, which was designed by Frank Lloyd Wright and is about 3 miles from the gardens.

• Address: 318 Spring Creek Rd, Rockford, IL 61107
• Hours: Open daily

Reserve a tour at least two weeks in advance. The tour cost is $60 per person.

Check Out Nicholas Conservatory & Gardens, Sinnissippi Gardens, And Sinnissippi Park

The Nicholas Conservatory and Gardens features a wide variety of exotic plants including tropical flowers conserved mostly in a beautiful indoor setting. The 11,000-square-foot conservatory routinely hosts intriguing plant exhibits, among them the annual orchid display.

The butterfly house is another fascinating exhibition that showcases the lifecycles of butterflies and moths, including when they emerge from their chrysalises.

Outdoors, the environment is even more stunning with more plant and tree species, a scenic Eclipse Lagoon, a waterfall, and fountains. There are also patio areas to take a break at, and a riverfront path that offers scenic views of Rock River while directly leading to the adjacent Sinnissippi Rose Gardens.

At the rose gardens, there are thousands of rose flower plants of different varieties which create a truly magnificent scene when they bloom. Just across the road (east of N 2nd Street) is Sinnissippi Park which is a public park. It offers a tranquil ambiance with its lush greenery and is a good spot for leisurely strolls.

The park typically hosts concerts in summer, including at the open-air Sinnissippi Park Music Shell which is a uniquely-designed amphitheater.

The Festival of Lights is another popular event typically hosted at the park in the winter months.

Induce An Adrenalin Rush At Six Flags Hurricane Harbor, Rockford

The spot packs numerous adventure and activity-packed attractions ideal for a family day out and was formerly known as Magic Waters Park.

Just off Interstate 90/39, Hurricane Harbor located in Cherry Valley offers water slides, a lazy river for some water-based fun and relaxation, and several play areas.

The Typhoon Terror, a tube water slide, is one of the hot favorites in the park. It has exhilarating twists and turns, which are experienced on a 4-person raft taken through the whooshing waters and wind action.

For adrenaline junkies, the Riptide Rush is just the right stop, with its near-vertical speed slide of 75 feet. On its part, the Abyss takes sliders on a descent of five stories in darkness, treating them to unpredictable twists and turns before they land in the pool below.

If visiting with young swimmers, the Caribbean Cove with its small water slide and spraying waterfalls will keep them actively entertained as they explore. Little Lagoon is another option for kids, with floating replicas of ocean animals and colorful water sprinklers to soak in as much fun as possible.

• Address: 7820 N Cherryvale Blvd, Cherry Valley, IL 61016
• Hours: Vary frequently; check the calendar before visiting
• Cost: Single-day tickets start at $30

Purchase passes for unlimited entry into the park for pre-determined durations and numerous other benefits.

Learn At The Burpee Museum Of Natural History

The Burpee Museum offers an appreciation of natural history in different aspects, and its exhibits and programs are curated for both adults and minors.

Classes suitable for adults include natural history art classes which offer fun ways to explore topics of the evolution of plant and animal species. To make learning interesting and interactive, art is thrown into the works with supplies provided for some exploration.

In terms of displays and exhibitions, there is enough to peak one’s imagination and curiosity. Dinosaur fossils, replicated forests, and re-enacted living environments of indigenous communities are some of the displays in the museum.

For travelers fascinated by topics of dinosaurs and evolution from the pre-ice ages, the Burpee Museum of Natural History is a place to visit.

• Address: 737 N. Main Street Rockford IL, 61103
• Hours: Monday-Sunday: 10:00 am - 5:00 pm. Closed over Christmas Eve and Christmas Day, Independence Day, Labor Day, Thanksgiving Day, and Easter

RELATED: What To Do In The Windy City: The Ultimate Travel Guide To Chicago

Sample More History At The Historical Discovery Center Museum

The museum definitely deserves a spot in the list of the most family-friendly museums in the US . It is an ideal spot for a fun-laden family outing where children get to learn a lot of scientific concepts from hundreds of interactive exhibits. It is a place to raise the interest of children in Science Technology Engineering and Math concepts in a hands-on, but entertaining way.

Visitors are able to discover fascinating exhibits showing human anatomies, space travel devices, a broad range of machinery, intricate electricity and lighting concepts, and other diverse scientific creations . This makes the museum a great spot for student visits.

Located on the banks of Rock River, the museum also features the Rock River Discovery Park which has a water play area, a fascinating maze, and dinosaur pits for some playful exploration.

The museum is housed at the Riverfront Museum Park complex which is a humanities and arts complex in downtown Rockford. The complex also houses the Rockford Art Museum and is connected to the Burpee Museum of Natural History by a walkway tunnel.

Visit The Tinker Swiss Cottage Museum And Gardens

Like the other attractions in Rockford, this museum also offers a reason to skip Chicago and try other Illinois destinations . It features the famed house museum, carriage house, and barn which belonged to the Tinker family. The attraction bears remarkable history relating to the foundation of the city and stores thousands of items documenting the life of the famous family.

The vintage Swiss architectural style which captivated Robert Tinker in his tour of Europe in the 1860s is among the few remaining in the US. The family also planted immaculate gardens around the cottage, creating a quaint and serene environment outside.

The museum depicts what the Victorian lifestyle was like in Rockford. Appreciate the cottage’s original furnishings, clothing used by the family in that era, diverse pieces of art, and general household items which are splendidly preserved.

The museum grounds also hold a pre-Columbian conical mound which is associated with the burial rites of Native American communities.

In addition to guided tours, visitors can explore the museum and gardens through open-house events, family game days, lectures, and members-only days.

• Address: 411 Kent St, Rockford, IL 61102
• Hours: Tours are offered between Tuesday and Sunday at 1 pm and 3 pm
• Cost: $9 for adults; $8 for seniors aged 65+; $5 for children aged between 6–17 years; free for children aged 5 years and below.

Visitors need to book guided tours to be allowed entry into the museum. The walking tours may take anything from 60 to 90 minutes.

Ethnic Heritage Museum And Graham-Ginestra House Museum

With its shared campus, the Heritage Museum Park connects the two fascinating museums, making it a convenient location to immerse oneself in a history-themed exploration.

The Ethnic Heritage Museum offers six galleries stashed with remarkable artifacts documenting the lives of the immigrant groups that primarily settled to the south of Rockford. It takes visitors through some of the important aspects of African-American, Lithuanian, Polish, Italian, Hispanic, and Irish immigration.

The galleries include some of the earliest maps of Rockford, vintage clothing, and diverse photography which tell the stories of the entry of these communities into Rockford.

On its part, the Graham-Ginestra House is symbolic of the industry of prominent families which established successful enterprises in Rockford in the 1800s. The architectural style of the house features both Greek and Italian influences and is on the National Register of Historic Places in Illinois.

• Address: 1129 South Main Street in Rockford, IL 61101
• Tour Hours: Guided tours are offered on Sundays from 2.00 pm to 4.00 pm. For private weekday tours, prior booking is required.

RELATED: 14 Quirky Roadside Attractions In Illinois Worth A Road Trip

Check Out The Fascinating Midway Village Museum

This museum takes you back to life in the Midwest in the era between the late 19th and early 20th centuries. Guided tours of the 13-acre Victorian-era village take visitors through historical interpretations of life in a typical village in northern Illinois. Self-guided tours of the village are also permitted, though access to the buildings may be limited without a guide.

At the main museum center, there are interactive exhibits further exploring the history of Rockford, and these too can be experienced by self-guided tours.

The “Many Faces One Community” exhibition is outstanding in its depiction of the earlier lives of immigrants from various backgrounds who settled in Rockford to create the thriving community that the city is today.

If interested in the technologies of the early 1900s, venture out to the Woodward Millhouse by Lake Severin to see the waterwheel.

• Address: 6799 Guilford Rd, Rockford, IL 61107
• Hours: Vary with seasons. Confirm the hours online to avoid inconvenience
• Cost: Range from $9 to $13 depending on the age of visitors, the exhibits targeted, and whether the tours are guided or not. Special events are charged separately

RELATED: 11 Interesting Things to Do in Illinois (That Aren't in Chicago)

Catch A Concert At Coronado Performing Arts Center

The 2,400-seat theater built in 1927 is a historic and significant entertainment hub in Rockford. Musical concerts, Broadway performances, comedic shows, and symphony orchestras are some of the events that revelers can catch here.

Another remarkable feature of the theater is its architecture. Its gilded interiors are reminiscent of the Spanish and Italian styles common in theater designs at the beginning of the 20th century.

To appreciate this style and ambiance, one may book a tour of the theater spaces and its stage.

• Address: 314 N. Main St. Rockford, IL 61101-0476

To enjoy a performance or show at the theater, browse the theater’s website for upcoming events and purchase tickets in advance.

Explore Rock Cut State Park

Nestled in the outskirts of Rockford about 10 miles away, Rock Cut State Park is a sprawling 3,092-acre park that offers an array of outdoor activities. The park is home to two lakes, perfect for fishing and boating, and over 40 miles of trails for hiking, horseback riding, and cross-country skiing.

Its diverse wildlife and picturesque landscapes make it a haven for nature enthusiasts. The park is open year-round, allowing visitors to enjoy the changing seasons.

• Address : 7223 West Lane Rd, Loves Park, IL 61111, United States
• Hours : Winter: 8 am - 5 pm (daily) Summer: 6 am - 10 pm (daily)

Visit The Rockford Art Museum

The Rockford Art Museum is located in the heart of the city, and it houses a remarkable collection of contemporary and modern art. The museum, established in 1913, features over 1,900 works, including paintings, sculptures, and photography.

Visitors have the chance to immerse themselves in the world of art through the museum's changing exhibits and educational programs.

• Address : 711 N Main St, Rockford, IL 61103, United States
• Hours : Thu - Sun: 10 am - 5 pm (closed From Mon - Wed)
• Admission : Free

Venture To White Pines Forest State Park

White Pines Forest State Park is a tranquil retreat known for its towering white pine trees. The park's scenic beauty is complemented by the Rock River that meanders through it, offering opportunities for fishing and canoeing.

The park also features cabins for those who want to extend their visit, making it a perfect weekend getaway.

White Pines Forest State Park is found about 34 miles from Rockford, about a 45-minute drive.

• Address : 6712 W Pines Rd, Mt Morris, IL 61054, United States
• Hours : 6 am to 6 pm (daily)
• Cost : Free

Visit Macktown Living History Education Center

The Macktown Living History Education Center is a historical gem that transports visitors back to the 1830s. This site was once the hub of Stephen Mack Jr., a fur trader, and his wife, Hononegah, a Native American woman from the region.

Today, the center is a living history museum that offers visitors an opportunity to experience life as it was in the 19th century. The center's grounds are home to several original and reconstructed buildings, including the Mack house, a trading post, and a blacksmith shop.

Tourists can stroll through these structures, absorbing the atmosphere of a bygone era.

• Address : 2221 Freeport Rd, Rockton, IL 61072, United States

Members get free admission to events and discounts at the museum shop. Those who often visit these parts may consider becoming members to enjoy these benefits.

Best Time To Go

With its location in the Midwest, Rockford has four distinct seasons. Winters in Rockford can be extremely cold with the possibility of snowstorms. January is the city’s coldest month, and temperatures can dip to just above freezing.

The period between March and June generally sees increased rainfall potential, often with the possibility of thunderstorms.

The peak times for visits to the city’s attractions are summer and the fall; as the weather is warm and fairly humid at this time. In particular, the period between July and October is an appropriate time to visit given the fall in rainfall intensity.

RELATED: Heart Of The Midwest: The Ultimate Guide To Ames & Things To Do

Nevertheless, the best time to visit is probably best determined by the attractions targeted. If interested in outdoor botanical gardens and parks, the period towards the end of spring may see the plants and flowers start to bloom beautifully. However, the high probability of rainfall may dampen outings, and visits to indoor attractions like museums are more appropriate.

In summer and towards the beginning of the fall, outdoor activities are generally more enjoyable, though charges may marginally increase because of higher demand.

What To Know When Visiting

• After the decline of its manufacturing industry starting in the 1950s, Rockford has sought to steadily diversify its economy. Service sectors such as tourism play a key role in this regard.
• The city’s rail system is largely dysfunctional. However, public bus transportation covers many routes and serves the city pretty well.
• Winters may be bitterly cold, and visitors ought to take sufficient precautions if they choose to travel through Rockford at this time. Take advantage of the winter visit to Rockford to venture further to the southeast for the fancy holiday attractions in Chicago .

RELATED: Midwest United States Travel Guide - Top Sights, Restaurants & Accommodations

Best Ways To Get Around

There are several options for getting to and from Rockford’s attractions. In terms of travel from locations outside the state of Illinois, the Chicago O’Hare International Airport is the most used option by passengers. It offers connections to and from various locations both in and outside the US.

Chicago's Midway International Airport is another popular option for travel to Illinois before proceeding to Rockford. There are bus shuttle services ferrying passengers into Rockford City from both Chicago airports.

Rockford also has an airport, the Chicago-Rockford International Airport, but it is mostly served by Allegiant Air which offers travel to limited destinations. One can also travel to or from the airport aboard chartered flights.

Once within the city, there are plenty of transportation options. The Rockford Mass Transit District provides public transportation, with the Downtown Transfer Center acting as the main stop, with connections to approximately 14 routes. The eastern parts of Rockford are served by the East Side Transfer Center.

The stops provide restrooms, vending machines, and waiting areas, and travelers can also catch Van Galder Buses to destinations like Chicago.

For more private travel, there are car rental services, and ride-hailing apps can also come in handy.

Where To Stay

There are plenty of both affordable and pricey accommodation options in Rockford. Some hotels to try out include:

Hilton Garden Inn Rockford

The accommodation is located just 2.1 miles away from the Midway Village Museum and less than 20 minutes away from downtown Rockford. It also offers direct access to the Anderson Japanese Gardens which is about 25 minutes away.

A number of restaurants, parks, golf clubs, and convenience stores are within a radius of 10 miles from the inn, with Rockford Casino less than a mile away.

• Address: 7675 Walton Street, Rockford, IL 61108
• Amenities: internet, indoor pool, meeting rooms, pet friendly, EV charging, parking, fitness center
• Cost: Rooms start at above $100

Radisson Hotel & Conference Center Rockford

This is the ideal accommodation for both business travelers and vacationers seeking to explore Rockford’s attractions. Its rooms provide a relaxing feel, with sufficient amenities to plan one’s adventures or work.

• Address: 200 South Bell School Road, Rockford, IL 61108
• Amenities: Wi-Fi, indoor pool, business center, on-site pub

Embassy Suites by Hilton Rockford Riverfront & Conference Center

A luxury hotel that puts guests right at the center of all the action in downtown Rockford, offering views of the Rock River. Moreover, it is close to attractions such as Rockford Theater, Rockford Art Museum, Discovery Center Museum, and Burpee Museum of Natural History all of which are less than 1 mile away. It is also right next to Davis Park which borders Rock River.

• Address: 416 S Main St, Rockford, IL 61101
• Amenities: Wi-Fi, fitness center, meeting rooms, golf simulator, indoor pool, hot tub, onsite restaurants
• Cost: Suites start at above $100

Red Roof Inn Rockford East-Casino District

The family-friendly establishment is strategically located to offer proximity to various comforts like restaurants. It is a walking distance away from Rockford Casino, and just 1.7 miles from Midway Village Museum.

• Address: 7434 E State St, Rockford, IL 61108
• Amenities: pet friendly, Wi-Fi, free parking, snack center
• Cost: Rooms start at below $100

Alpine Inn and Suites

This affordable accommodation is located centrally to offer easy access to plenty of Rockford’s attractions. It is near downtown Rockford at the junction of E State St and N Alpine Road, and is within easy reach of a number of conveniences such as restaurants, stores, and medical facilities. It is also close to Alpine Park and Alpine Hills Golf Park.

• Address: 4404 E State St, Rockford, IL 61108
• Amenities: Wi-Fi, parking

Where To Eat In Rockford

Rockford has plenty of dining options for visitors to enjoy.

Breakfast Options:

• Eggsclusive Café, Johnny Pamcakes, Fresco at the Gardens (at Anderson Japanese Gardens), The Norwegian, Lydia’s Café, Swedish Pancake House, Alpine View Restaurant, IHOP, Stockholm Inn

Lunch, Dinner and Drink Options

Lino’s Rockford

The eatery serves various Italian delicacies, including mouthwatering pizzas and delectable wines, as well as some varieties of seafood. Moreover, one can have their special event hosted at the restaurant, or get catering services brought to their destination.

• Address: 5611 E State St, Rockford, IL 61108
• Hours: Sunday-Thursday
• Cost: Main dishes start at $16 per serving

Sister’s Thai Café

The café is a great spot to sample Thai food varieties like curries and fried rice or noodles. One can get combinations of dishes made from light, but delicious and healthy ingredients.

• Address: 514 E. State Street Rockford, IL 61104
• Hours: Open daily, except for Sunday
• Cost: Main dishes start at $15 per serving

Uncle Nick’s

The restaurant services Greek and American cuisines, with several fast food options for takeout. Their Gyros sandwiches are a favorite, and there are delicious appetizers on the menu too.

There are two Uncle Nick’s eateries in Rockford.

• Address: 918 E State St, Rockford, IL 61104; 5404 E. State Street Rockford, IL 61108
• Cost: Dishes start at $3

Irish Rose Saloon

The restaurant prepares delicious Irish and American dishes from fresh ingredients sourced in Chicago every week and prides itself on serving preservative-free delicacies. The downtown restaurant and saloon provides a cozy ambiance, plus a variety of cocktails, wines, and beers to choose from.

• Address: 519 E State St, Rockford, IL 61104
• Cost: Dishes start at $11

Hai Quynh Restaurant

If seeking Asian delicacies, this is the restaurant to go to for some amazing Vietnamese dishes. One can choose from rice cuisines to various soups and noodles, and the prices are pretty affordable.

• Address: 324 7th St, Rockford, IL 61104
• Cost: Dishes start at $2.50

How To Spend A Perfect Day In Rockford

Start the day with a mid-morning visit to the Six Flags Hurricane Harbor for some adrenaline-packed water slide activities.

Head to the Typhoon Terror slide or the Abyss with its twists and turns. Submit to the whooshing water action before plunging into the pool below. After soaking in enough fun, head to the nearby Alvarez Restaurant for some Mexican bites and drinks to replenish the lost energy.

Once done with lunch, head to the Nicholas Conservatory & Gardens on the banks of Rock River to enjoy the tropical plants and flowers on display. Be sure to check out the butterfly and orchid exhibits.

When done with the conservatory, stroll outdoors and revel in the magnificent views. Walk along the riverfront path towards the adjacent Sinnissippi Rose Gardens.

Enjoy the variety of rose flowers and take pictures. If the weather and time permit, stroll along the riverfront path some more while enjoying the beauty of Rock River.

Afterward, head to the Embassy Suites by Hilton Rockford Riverfront & Conference Center where a suite had been reserved. Shower and freshen up then head to the hotel’s restaurant for dinner.

Once done, change into something chic and comfortable and walk to the Rockford Performance Arts Center to catch a performance.

After enjoying the concert or show, head back to the hotel to retire for the night.

Q: What is Rockford IL famous for?

Rockford is the seat of Winnebago County and is located on the banks of Rock River. It is renowned for its beautiful gardens that rival Chicago's famous botanic garden , museums preserving its fascinating history, and cultural entertainment spots. Rockford was also given the nickname "Forest City" because of its greenery and parks.

Some of its top tourist attractions include Anderson Japanese Gardens, Coronado Performing Arts Center, Burpee Museum of Natural History, and the Tinker Swiss Cottage Museum.

Q: Is Rockford IL worth visiting?

Rockford is one of the cities in the state of Illinois , and it is located to the northwest of Chicago. It is in Winnebago County and is largely out of Chicago metropolitan area.

Because of the proximity, however, the city's profile is significantly impacted by Chicago. For instance, many travelers into Rockford use the Chicago O'Hare International Airport.

Q: What is there to do in Rockford, IL at night?

Nightlife in Rockford, IL is pretty vibrant, and there are a number of activities to try out. One can catch a concert, comedy, or Broadway show at the Coronado Theater. AMC Theaters also shows interesting movies of different genres and can be a nice spot to spend part of the night at.

If seeking a bit of rum and relaxation, head to the city's sports bars and nightclubs which routinely host musical events featuring various local talents.

Alternatively, one can head over to Hard Rock Rockford Casino or Mabel's Jackpot to try their luck at the slot machines and game tables available.

Awesome, you're subscribed!

Thanks for subscribing! Look out for your first newsletter in your inbox soon!

The best of Chicago for free.

Sign up for our email to enjoy Chicago without spending a thing (as well as some options when you’re feeling flush).

Déjà vu! We already have this email. Try another?

By entering your email address you agree to our Terms of Use and Privacy Policy and consent to receive emails from Time Out about news, events, offers and partner promotions.

Love the mag?

Our newsletter hand-delivers the best bits to your inbox. Sign up to unlock our digital magazines and also receive the latest news, events, offers and partner promotions.

• Things to Do
• Food & Drink
• Time Out Market
• Coca-Cola Foodmarks
• Attractions
• Los Angeles

Get us in your inbox

🙌 Awesome, you're subscribed!

The best weekend getaways from Chicago for families

Take a break from the city and find family-friendly activities throughout the Midwest on these weekend getaways.

Chicago boasts plenty of kid-friendly activities  and restaurants , but if you're planning a family vacation, there are many approachable, fun and memorable destinations close by for a weekend away. Cities, state parks and lakes across the region are full of hiking for all ages and engaging, hands-on ways to learn about history, ecology and wildlife. Along the way, discover quirky shops, longstanding eateries with decadent desserts and recreational activities that kids of all ages will enjoy. From wacky and weird to active and relaxing, here are the best  weekend getaways from Chicago for families.

RECOMMENDED:  The best day trips from Chicago  RECOMMENDED:   The most unique day trips from Chicago

An email you’ll actually love

Family weekend getaways from Chicago

1.  Wisconsin Dells, WI

Driving time from Chicago: Three hours The waterpark capital of the world—what's not to love? It doesn't matter if the weather is sunny or rainy, though, because this Wisconsin town offers both indoor and outdoor parks. Mt. Olympus is one of the biggest and most popular, with both water and theme park attractions (and rides for the really little ones as well). Those looking to do something a little different can visit MagiQuest in the Great Wolf Lodge to participate in a live-action role-playing game. If the little ones come up for air long enough to eat, head to Buffalo Phil's , where kids get their food delivered on a train before spending some coinage in a giant arcade. Paul Bunyan's is a fun, themed spot for an all-you-can-eat breakfast.

If you're looking for animals, look no farther than Timbavati Wildlife Park for behind-the-scenes tours with exotic animals. Or let the kids feed gentle deer at Wisconsin Deer Park .

2.  Hamilton County, IN

Driving time from Chicago: Three hours Take a trip back in time at the Conner Prairie Interactive History Park  and explore 1836 Prairietown, see a Civil War reenactment or stroll along the nature walk. There’s also a large Swiss Family Robinson–esque tree house called Treetop Outpost for the whole family to enjoy. Then, of course, there's Conner Prairie’s tethered helium balloon, which elevates guests 377 feet above the prairie for unbeatable views over Indiana.

Nearby, you can take to the more than 300 miles of trails in the county, including paved paths that lead to shopping, dining and sightseeing. Bring your bike or rent one during your stay.

3.  Lake Geneva, WI

Driving time from Chicago: One and a half hours At a sprawling resort like the Grand Geneva , you can count on plenty of activities to keep the family busy. Explore the Dan Patch Stables , where the kids can go on pony rides and feed the animals in the free petting zoo. Waterpark lovers will clamor for Moose Mountain Falls , a 50,000-square-foot waterpark. For dinner, check out Popeye's (not the chain with an amazing fried chicken sandwich): It's super family-friendly with great views of the water and a large menu.

4.  Door County, WI

Driving time from Chicago: Four hours

A longtime favorite of Chicagoans seeking a bit of R&R, Door County has more to do than your family will be able to fit into just one weekend. Kids will make some amazing memories with the host of experiential activities, like feeding a baby goat at The Farm ,  making their own crafts at Hands On  or ziplining, gem mining or go-karting at Egg Harbor Fun Park . More active families will love exploring the stunning Cave Point County Park --you can even get kayak cave tours or stand-up paddleboards through Gravity Trails . 

The region isn't short on kid-friendly restaurants either -- go for highly cutomizable wood-fired pizzas at Wild Tomato or watch goats graze on the roof at Al Johnson's Swedish Restaurant and Butik . And don't forget to stop at Door County Creamery for some indulgent gelato. 

5.  Indianapolis, IN

Driving time from Chicago: Three hours Indianapolis has enough indoor and outdoor activities for a fun-filled weekend. Head to  The Children's Museum of Indianapolis  for top-notch exhibits like the planetarium and the Dinosphere, where kids can dig for dinosaur bones. It also has a great play area for toddlers. For some fresh air, walk or bike along the Monon Trail, a 10.5-mile path that runs through most of Indy. Stop in the Broad Ripple neighborhood to browse some shops and grab a scoop of ice cream at Brics .

Rest your weary heads at the Crowne Plaza Downtown Indianapolis Union Station , and be sure to call ahead to check for family packages that may include lodging plus tickets to attractions like the Children's Museum and  Indianapolis Zoo .

6.  Holland, MI

Driving time from Chicago: Two and a half hours Since the mid-19th century, the small city of Holland has been home to wooden shoes and tulips. Whether you're there in time for the Tulip Time Festival in May or want to visit the Windmill Island Gardens , the family will have a blast. Check out a working 250-year-old Dutch windmill—”De Zwaan,”—or stroll 36 acres of pristine lawns; bring your picnic blanket and a camera for a vibrant family photo op. During the day, catch a tour of the 125-foot windmill from a guide in traditional plaid Dutch garb. Need even more flowers? See more than 5 million in bloom in April and May at Veldheer Tulip Gardens . To take home a piece of Holland, though, you must not miss De Klomp Wooden Shoe and Delft Factory , where you can also enjoy a free tour of the famous, centuries-old pottery maker from the Netherlands. Once you've worked up an appetite, take the kids out for an authentic Dutch dessert like sugar bread from deBoer Bakkerij . If you need to burn off some energy, a 20-minute drive takes you to Saugatuck Dunes State Park . Surrounded by 300 acres of nature and dunes that rise up to more than 200 feet tall, you won’t have a care in the world running and playing along this long, sandy shore.

7.  St. Louis, MO

Diving time from Chicago:  Five hours

Brimming with attractions, St. Louis is perfect for families. The iconic Gateway Arch is an absolute must—you’ll understand why when you reach the top of the 630-foot-tall monument—but don’t miss the interactive, immersive City Museum , an educational playground with slides, sculptures you can play on and even vintage pinball machines. If nature’s your thing, the Missouri Botanical Garden has one of the largest Japanese gardens in North America, the Saint Louis Zoo is free and home to more than 600 species of animals and the St. Louis Aquarium features a 250,000-gallon shark habitat.

8.  Peoria, IL

Driving time from Chicago: Two and a half hours

There’s plenty of family-friendly history, recreation and adventure in Illinois’s oldest European settlement. Enjoy the scenic views and watch the barges go by along the RiverFront District before making a stop at the The Peoria Riverfront Museum to immerse yourself in space shuttle launches, solar systems and eclipses in the domed planetarium. Then fill up on smoked meats and burgers at The Blue Duck Barbecue Tavern , housed in a repurposed train depot utilized from 1899 to 1978. Sleep close to the activities at the Mark Twain Hotel , a quaint and understated 111-room accommodation 10 minutes walking from the RiverFront.

You’ll also find lots of greenery and wildlife to experience, even within city limits. Spend time at the 60 square miles of parks—the oldest park district in Illinois. Wander around the 5-acre Luthy Botanical Garden for year-round floral beauty or hike through seven miles of trails in Forest Park .

9.  Harbor Country, MI

Driving time from Chicago: One hour and 15 minutes With a population of less than 2,000 permanent residents, the small lakefront city of New Buffalo is charming for all ages. If traveling by train, Amtrak will drop you off near The Harbor Grand , where a stay feels like home but cozier, with an in-room fireplace and harbor view (or glimpse of a frozen lake). During warm months, you can hop on one of the hotel's bikes for a quick ride around town. And kids will always get a kick out of the nearby Hesston Steam Museum and Captain Mike's Fun Park . For lunch, Redamak’s is the popular burger joint in the area, filled with fun activities for kids, including a mini firetruck. And what would a visit to a beach town be without ice cream? Don’t miss funky Oink's Dutch Treat Ice Cream & Yogurt Shop . For dinner, visit the hotel’s Terrace Room  for a comforting Italian dish like spaghetti and meatballs (described as Grandma’s family recipe with sweet marinara) that everyone will love. Or pop over to Bentwood Tavern for wood-fired pizza.

10.  Gurnee, IL

Driving time from Chicago:  45 minutes

If you’re taking the family up north for a day of fun and games at Six Flags Great America , why not make a weekend out of it? Aside from the amusement park, the village of Gurnee is also home to Great Wolf Lodge —a resort with an 80,000-square-foot indoor water park. Once you’ve dried off, shop ‘til you drop at outlet mall Gurnee Mills .

For even more activities, make the short drive across the border to Kenosha for America's Action Territory Fun Park , where you'll find everything from bumper boats and cars to laser tag and batting cages. The youngins’ can gaze at dinosaur fossils and learn about the link between the prehistoric reptiles and birds at the Dinosaur Discovery Museum , or climb to the top of Southport Lighthouse for sweeping views. There are also a ton of adventures to be had at the Bristol Renaissance Faire during the summertime, when fairgoers dressed in costumes converge on a recreated 16th century port city.

11.  Ottawa, IL

Driving time from Chicago: One and a half hours In just an hour and a half, you'll be transported to a beautiful setting filled with both water and land activities to keep your family entertained. Hike at nearby Starved Rock State Park  or Buffalo Rock State Park ; bike along the I & M canal trail that runs for more than 60 miles; take a dip in the on-site pool or build sandcastles and pack a picnic at the aptly named Picnic Grove. You can also rent a variety of boats, kayaks, water skis and canoes at a nearby private beach. Renting a cottage is the way to go, and you can find a lovely place to rest your head at Heritage Harbor .

12.  Battle Creek, MI

There are no picturesque tree-lined streets or Michelin-starred restaurants in the manufacturing hub nicknamed “Cereal City,” but it’s full of wacky family adventures. The home of Kellogg’s and Post Consumer Brands honors its origins with an annual CerealFest each June. If you miss it, venerate America’s favorite breakfast any time of year with a visit to The Calhoun County Visitors Bureau’s  "Cereal History" exhibit to journey through the history, manufacturing, and culture significance of Battle Creek native John Harvey Kellogg’s invention.

After some cereal nostalgia, meet rescued gators at the Critchlow Alligator Sanctuary twenty minutes south of Battle Creek. There are more than 180 alligators on site, including the 11-foot "Godzilla."( Don’t worry—staff only let the kids touch the small ones.)

Grab dinner a turkey buffet dinner at Cornwell’s Turkeyville USA and then stay for one of the venue’s rotating musicals or theatre performances. For those who prefer more traditional animal encounters, you can glimpse lions, zebras and giraffes at Binder Park Zoo .

As the sun sets over Goguac Lake, you can pretend you’re miles away from Southwestern Michigan at the ostentatious McMansion Paradise Island the Fantasy of the Nouveau Riche . Filled with regionally inappropriate nautical decor, this rental on the lake’s Clark Island sleeps 12, is only accessible by boat and features big windows that offer lake views.

13.  Northern Indiana

Driving time from Chicago: One hour and 40 minutes

With the charming university town South Bend as your home base, spend time exploring Northern Indiana’s outdoor expanses and Amish culture. Start with a visit to St. Patrick’s County Park , a 398-acre preserve with activities for any season. The park features year-round bird watching opportunities and hiking along the numerous trails of varying lengths, canoeing and kayaking along St. Joseph River in the summer and cross country skiing in the winter.

During summer visits, make time to browse outdoor markets running May through September. The South Bend Farmers Market and the Mishawaka Market  are both go-to spots for sampling local produce and artisanal cheeses and meats.

You can easily spend an entire day at Shipshewana Auction & Flea Market —the largest in the Midwest—located an hour drive east from South Bend. The size of more than 30 football fields, you’ll find antiques and vintage furniture, decor, apparel, food stalls, and even plants. On your way back to South Bend, make a stop in Middlebury, a town of around 3,500 with a strong Amish presence. Visit the original Rise ‘n Roll Bakery and Deli and grab a box of the notoriously addictive cinnamon caramel doughnuts.

14.  Springfield, IL

Driving time from Chicago: Three hours and 15 minutes

The capital of Illinois is full of history and things to do with the family. Tour the Old State Capitol —the spot where Abraham Lincoln announced his candidacy for the presidency—or visit the Abraham Lincoln Presidential Library and Museum to learn more about the nation’s 16th president and the American Civil War. Hit up sporting goods store SCHEELS for much more than just athletic apparel—the popular attraction also houses a Ferris wheel, 16,000-gallon aquarium, arcade and cafe. For some outdoor activities, the Henson Robinson Zoo is home to over 300 animals while Knight’s Action Park is a 62-acre water park with a mini golf course. 

15.  Walworth County, WI

If you’re looking for an off-the-beaten track destination to unplug and reconnect with nature, the Walworth County lakes within thirty five minutes of Lake Geneva are a no-brainer. At Delavan Lake, Whitewater Lake, Rice Lake, Lauderdale Lakes (comprised of three interconnected lakes) and nearby Lake Wandawega to the south and Pleasant Lake to the north, visitors can canoe, kayak, fish, swim and hike. Head south to the 12-mile White River Trail  for hiking, biking and horseback riding.

Whitewater Lake’s Scenic Ridge Campground  offers wooded or grassy campsites along the water, access to volleyball nets, horseshoe pits and hiking trails, plus an extensive calendar of sports, entertainment and activities for folks of all ages.

16.  Columbus, IN

Driving time from Chicago : Four Hours

You might be thinking “why would any kid enjoy a hub of modernist architecture?” However, this vibrant ode to inventive constructions can be appreciated by all ages. The vibrant pavement in the city center and colorful bridges are just enough to keep the kids captivated. If that’s not enough, a three-story children’s museum is always an option. 

A must visit in this eccentric town is Zaharakos Ice Cream Parlor and Museum , an authentic ice cream shop that opened in 1900. For dinner, family-friendly ZwanzigZ Pizzeria and Brewery has something for everyone. 

17.  Brown County, IN

Brown County State Park is famous for its vibrant fall colors, but this nature oasis 30 minutes northeast of Bloomington is fun during any time of the year. Indiana’s largest state park often referred to as the “Little Smokies” has 11 hiking and 14 mountain biking trails of varying lengths and difficulty levels—plus, 20 miles of roads for when your legs get tired—you can mix and match for your desired adventure, whether it's to see stunning views of rolling tree-covered hills and waterfalls or to feel immersed in the backcountry. If you need to rent two-wheeled transport, stop by Q’s Bikes .

There are plenty of campsites around the park, but for indoor stays head just outside the park boundaries to Nashville, a small town full of mom-and-pop craft stores, fudge shops, ice cream and restaurants with live entertainment. Cornerstone Inn has a campus of 41 affordable accommodations around town and a cabin in the woods. The delicious pizzas and craft beer at Big Woods are much needed fuel after an active day—and don’t skip the sizzling skillet cookie topped with ice cream.

18.  Galena, IL

Driving time from Chicago: Three hours

Words people use regularly to describe Galena include “quaint,” “charming” and “historic,” but none of those have to also mean “boring.” One of the best all-ages options for more active families is the Chestnut Mountain Resort , a 100-room lodge featuring skiing and snowboarding in the winter and ziplining and a 2,050-foot alpine slide in the summer. 

If you don’t want to go the resort route, there’s still plenty to do in the great outdoors with the whole family, from kayaking or canoeing down the Galena River with a rented vessel from Nuts Outdoors to a scenic trail ride with the Shenandoah Riding Center to strawberry picking at Terrapin Orchards . For a fun, family-friendly evening activity, catch some thrilling illusions at the P.T. Murphy Magic Theater or get your nostalgia on with a drive-in movie at the Midway Drive-In in nearby Sterling. And if you’re browsing through downtown Galena, don’t forget a stop for some sweets at Galena Kandy Kitchen . 

19.  Ann Arbor, MI

There are plenty of reasons to take a family road trip to Ann Arbor, even when it isn’t Michigan football or basketball season. Kids can spend hours at the interactive Ann Arbor  Hands-On Museum or the Leslie Science and Nature Center, where they can run around the Nature Playspace and get up close with birds of prey in the raptor enclosure, or snakes and frogs in the Critter House. The whole family will find something to love exploring the shops and restaurants on colorful Main Street—the little ones will be particularly drawn to the nostalgic soda and sweet shop Rocket Fizz and the countless shelves of books, comics, toys and games at Vault of Midnight .

As for going out to eat with your whole crew, even the breweries here cater to craft beer enthusiasts with kiddos— Blue Tractor BBQ & Brewery and Jolly Pumpkin offer award-winning brews and hearty, creative food for the parents, with solid kids menu options and crowd-pleasing desserts. Speaking of dessert, a trip to Zingerman’s Deli for their decadent brownies is also a must.

20.  Casey, IL

Just under a four hour drive from Chicago, the small town of Casey is home to some of the world’s largest items. From a 28-foot Chevy truck Key to a 46,000-pound rocking chair, these public sculptures are best seen in person. Stop by to see 12 of the record-holding world’s largest items. It’s a great day whenever kids feel like they’ve been shrunken down to the size of an ant.

Stay at the quaint and comfy Eighteen-Nineteen Sleepover Hotel while planning your sightseeing around the city. Locals love the Wildflower Bakery and Candy Company and it’s a great treat to keep the kids happy. For any java-dependent parents running on fumes, the Casey Coffee Company is conveniently located right between the World’s Largest Rocking Chair and the World’s Largest Mailbox.

Family-friendly day trips

Family-friendly day trips from Chicago

With new states to explore just a short drive away, Chicago is perfectly situated for a quick jaunt to regional wonders with the little ones in tow.

[image] [title]

Discover Time Out original video

• Press office
• Investor relations
• Work for Time Out
• Editorial guidelines
• Privacy notice
• Do not sell my information
• Cookie policy
• Accessibility statement
• Terms of use
• Copyright agent
• Modern slavery statement
• Manage cookies
• Advertising

Time Out products

• Time Out Worldwide

Time Out magazine