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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

Harrison Pierce

María Casbas

CNT Editors

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.

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24 Top Weekend Getaways From Chicago

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

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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

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3 Days in Chicago: The Ultimate Weekend in Chicago Itinerary

Chicago is a vibrant city that feels very alive, and with the perfect 3 days in Chicago itinerary, it’s possible to sample the best of the city over a long weekend!

The city is always on the move, and there isn’t an hour in the day that you won’t find at least 10 unique and adventurous things going on around town.

Music and food festivals pull out all the stops in Chicago, on top of the arts and cultural events that dot the city throughout the year.

Are you into food and drinks, lake views, and most of all, fun? Then Chicago is the place to be. There is enough here to explore for months, and we are going to pack all of the best events and activities into a 3 day long weekend itinerary to experience the essence of Chicago. 

Note: this Chicago blog post was written for Our Escape Clause by former Chicago locals Zach & Julie Ruhl, the travel couple behind Ruhls of the Road . Thanks for joining us, guys!

Table of Contents

Day 1 in Chicago Itinerary: The Bean, Skydeck & Great Chicago Food

Day 2 in chicago itinerary: lincoln park, wrigley field & beyond, day 3 in chicago itinerary: magnificent mile, navy pier & an afternoon adventure, where to stay for 3 days in chicago, where to eat during your chicago weekend getaway, getting around during 3 days in chicago, when to spend a long weekend in chicago.

Some links in this post may be affiliate links. If you make a purchase through one of these links, we may earn a small commission at no extra cost to you. Please see our disclosure policy for more detail.

Chicago is an enormous place. The city covers miles in each direction, with awesome things to do located all over the map. Therefore, this Chicago itinerary is going to thoughtfully take you from place to place, minimizing travel time and maximizing adventure.

Your first day in any new city should no doubt include some of the most signature sightseeing highlights there–and this Chicago itinerary is no exception, starting with a popular activity that is relatively new in Chicago: the Riverwalk. The current version of the Riverwalk was completed in 2017 and is an excellent place to start your Chicago weekend getaway.

Start your weekend in Chicago with a walk on the Chicago Riverwalk.

The Chicago Riverwalk starts at Wolf Point, near where the Chicago River turns from East/West to North/South. From there, the Riverwalk continues for over a mile, to the point where the Chicago River meets Lake Michigan.

Along this beautiful walk, you’ll pass a few awesome cafes and restaurants. This is a great place for a morning coffee, watching the morning hustle and bustle of America’s third-largest city. On top of that, the morning walk counts as your exercise for the day!

If you fall in love with the Riverwalk, then come back for a happy hour one evening. Riverside wineries and bars open up during the evening, complete with sets of outdoor games, live music, and some great entertainment! 

Check out Millennium Park.

At the end of the Chicago Riverwalk, you’ll reach Lake Michigan. Turn right here and head South to Millenium Park, where you’ll find an excellent location for soaking in the Chicago skyline from a beautiful park in the huge city center.

Millennium Park is an awesome Chicago sightseeing destination for two reasons. First off, it is just a great park full of fun things to do in Chicago !

There is an awesome playground for kids to play on, a great dog park for your four-legged friends, a huge green space to sprawl out for a picnic, a live music amphitheater, the Crown Fountain with a reflecting pool, endless gardens, and so much more!

You could spend a whole day at Millenium Park and not grow bored.

The second reason Millenium Park is so great is its proximity to everything. The park is great, but what makes it so impressive is that you are literally in a natural oasis amidst the concrete jungle of downtown Chicago.

Look around you while in the park, and you’ll see the towering structures of the Willis Tower, the Aon Center, and the rest of the enormous Chicago skyline.

Snap photos at The Bean.

At the edge of Millenium Park is The Bean, AKA Cloud Gate, Chicago’s most photographed (unofficial) monument.

The Bean is a huge monument, standing over 30 feet tall and 60 feet long, that is made of polished chrome and has no visible seams. This structure is truly unique and is an awesome downtown Chicago sight. 

The Bean is perfectly reflective, and due to its shape, the reflections can make for very fun images. It is essentially a gigantic magic mirror, placed in the middle of a bustling downtown environment.

Spend some time enjoying the fun reflections you can see as you walk in a circle around and under The Bean, then head for some food.

Downtown Chicago should have plenty of options on your way to your next stop: the Willis Tower. 

Admire views of Chicago from the Willis Tower Skydeck.

The Willis Tower is Chicago’s tallest building and the second tallest in the United States. At one point, this skyscraper was even the tallest building in the whole world, and held that title for 25 years! There’s no doubt that this is a must-see spot on any 3 day Chicago itinerary.

When you visit the Willis Tower, there are really two things you need to do. First off, admire the size of this monstrosity from below. The building literally reaches into the sky, and from the bottom seems impossibly huge. Walk around it marveling upwards, just make sure to lose your attention and wander into the city streets!

The other way to see the Willis Tower is, of course, from the top. The Skydeck is at the very top of the building, where you can see Chicago stretch beneath you for miles and miles in each direction into the horizon.

If you have the stomach for it, there is even a glass-bottomed section where you can literally step out into the sky, or at least it looks that way. From the glass floor, you can see down over 1,000 feet to the streets beneath you. This is quite an incredible experience and one that you won’t get anywhere else in the United States!

Book your Skydeck tickets for the Willis Tower today!

Finish your first day in Chicago in West Loop on Randolph.

The West Loop is an up-and-coming neighborhood in Chicago. This area seemingly has a great new restaurant pop up each week and has some of the most delicious food and one of the most fun atmospheres in the city.

Randolph Street in the West Loop is the culinary center of the neighborhood and is where you should head for dinner and drinks on your first day in Chicago. If you have the time and energy, the very best activity is to have a drink at a few different places, hopping from place to place and soaking up as much of this wonderful neighborhood as you can.

Each restaurant will have a unique vibe and atmosphere, so keep hopping around until you find the one you love best.

Want to make sure you experience the best food in the neighborhood? Add this popular West Loop Food Tour to your Chicago itinerary!

Close out your first night in Chicago at an Irish pub.

Chicago has a huge Irish population, and therefore quite a few Irish pubs located around the city. Our best recommendation is to find one close to your hotel and pop in for a Guinness as a night-cap. Enjoy the Chicago atmosphere, and then head to your hotel to get some sleep before heading off on your second day’s worth of fun things to do in Chicago!

Day 2 in Chicago is going to be a day full of exploring Chicago’s famous North Side. The North Side is awash with classic Chicago food options (Chicago loves its food…) as well as awesome sites to see and things to do. First up is the famous Lincoln Park.

Start the day with a stroll through Lincoln Park.

Lincoln Park is a huge and sprawling greenspace alongside Lake Michigan for 7 long miles. This is, in fact, the largest park in all of Chicago! And it also may very well be the most beautiful.

Alongside Lake Michigan, Lincoln Park has a few different beaches, as well as seemingly endless biking and walking trails. If you would rather bike than walk, then there are many bike rental options scattered all around the park, and around Chicago as a whole.

While strolling or biking through Lincoln Park, make sure to stop and see the Belmont Rocks, North Pond, and the Signal of Peace Monument. Along the way, admire the natural beauty and enjoy the sounds of birds singing as you bring on your second day in Chicago.

Soak up the sun at North Avenue Beach.

North Avenue Beach is one of Chicago’s largest and most popular beaches. Located right alongside Lake Michigan, this vast expanse of white sand makes for a great place to enjoy the beautiful Chicago summer sun.

If you are traveling with a group, then there are opportunities for some beach volleyball at North Avenue Beach! At the beach, you can rent a net and a ball (rentals are by the hour) and play some volleyball on the sand in view of the Chicago skyline!

While at North Avenue Beach, you must make a stop at the famous beach house that is shaped like a boat. This is also the location of Castaways, a bar and grill on the roof of the beach house serving yummy drinks with an incredible view. 

Head to Wrigley Field & Wrigleyville.

You can’t visit the North Side of Chicago and not see Wrigley Field. As one of the most famous baseball stadiums in existence, and the home of the Chicago Cubs, this is a must-see stadium, especially for sports fans.

Wrigley Field is located right in the heart of Wrigleyville on the North Side. Surrounded by residential areas and a huge bar and restaurant scene, this area is a magnet for good times, especially when the hometown Cubs are lacing up their cleats for a game.

If you are fortunate enough to be in Chicago while the Cubs are playing, head to Wrigley just for the experience of people watching and cheering on the hometown team. If you’d like, you could even try and buy some tickets, and usually, you can get a good deal on seats if you are okay purchasing them after the game is already in the 2nd or 3rd inning.

Wrigleyville, the neighborhood surrounding Wrigley Field, is an excellent place to hang out, have a drink, and hop around a few of the local establishments. Each of them has a great atmosphere, delicious, food, and of course a wide array of beers on tap.

Sample some Malort.

Malort is a Chicago specialty liquor and is something anyone over 21 should try when they visit the Windy City.

The liquor itself is not good because of taste, in fact, it tastes pretty bitter, and most people find it awful. However, it is all about the experience of trying something the locals love! If you’d like to experience the local culture of Chicago, then you have to try Malort at least once.

Finish the Day at the John Hancock Center Signature Lounge.

The John Hancock Center is the best building in Chicago. That may be a controversial opinion, but it is so true. The enormous slanted walls of the Hancock reach over 1,000 feet into the Chicago sky, with huge beams in a crisscrossing X pattern the entire way up. The building is an architectural masterpiece and is a wonder to see from the base.

The best place to experience the Hancock Center, however, is not from the base. It is from the Signature Room.

What is the Signature Room? It is an incredible 95th-floor bar and restaurant with an absolutely stunning view of Chicago. The Signature Room offers a 360-degree view of Chicago from above and is especially breathtaking as the sun sets and the sea of lights emerges beneath you.

Experiencing an evening at the Signature Room is a wonderful experience, and will be a highlight of your visit to Chicago. If you are visiting on a budget, just order a drink here, as dinner can be expensive!

Day 3 is going to be spent exploring more awesome sites and destinations in downtown Chicago. It is going to be a day where you can see as much as you want, and take it all in at your own pace. Choose your own adventure and make today special as you finish up your long weekend in Chicago!

Walk down the Magnificent Mile.

Start the day with a trip down the Magnificent Mile. This is a section of Michigan Avenue that is the retail center of Chicago. The street is lined on both sides with tons and tons of flagship stores, boutiques, and shopping malls.

Along the Magnificent Mile, in addition to all of the premier shopping, there are a few awesome sights you’ll see during this part of your Chicago weekend getaway.

The Wrigley Building is an awesome structure located right where Michigan Avenue meets the Chicago River. The Tribune Tower and the Chicago Water Tower are also wonderful landmarks along this stretch.

Explore Navy Pier.

Just a few blocks from the Magnificent Mile is Navy Pier, an absolute must-visit destination on any Chicago visit. The Navy Pier is, as the name suggests, a large pier, formerly used by the Navy, that extends straight out into Lake Michigan. 

These days, Navy Pier is an awesome destination that is used for a wide variety of attractions. First off, there is almost always some form of live entertainment or shows that are happening over a weekend at Navy Pier. On top of that, the pier is lined with awesome bars and restaurants, as well as shops and boutiques.

The view from the end of Navy Pier is excellent. First off, you’ll get to see the vast expanse of Lake Michigan on 3 sides of the pier. However, when you look back at the city, you’ll get a view of the full skyline including the Willis Tower and the Hancock Center. Do you want an even better view? Because there is one way to get it… There is a HUGE Ferris wheel that you can ride to get a stupendous view of the entire Chicago skyline and Lake Michigan!

Visit Buckingham Fountain in Grant Park.

After exploring Navy Pier, head to Grant Park, another of Chicago’s excellent downtown parks. Here you’ll have the chance to explore a huge area of green space, complete with monuments, statues, and a great lakeside walkway. At the heart of Grant Park, you’ll see Chicago’s most famous and beautiful fountain: Buckingham Fountain

Buckingham Fountain is at the center of Grant Park and is a great place to sit and enjoy a coffee or picnic. The fountain itself is beautiful, but it is made even better by the great Chicago skyline in front of you, and Lake Michigan behind.

Further South in Grant Park you’ll find three other excellent Chicago sightseeing spots to consider adding to your 3 day Chicago itinerary:

Field Museum, Shedd Aquarium + Adler Planetarium

On the south side of Grant Park are 3 beautiful buildings, each of which houses an awesome adventure. The Field Museum is one of the largest natural history museums in the world and is home to some of the best exhibits you can possibly imagine. When we visited in the past, the dinosaur exhibit left us astounded, as they had a full-size Tyrannosaurus Rex named Sue!

The Shedd Aquarium is a world-class aquarium located just east of the Field Museum on Lake Michigan. This aquarium is stunning both from the outside and inside and offers hours of exploration as you make your way through the grounds.

Finally, the Adler Planetarium, America’s FIRST planetarium, is a wonderful place. This place offers the chance to explore things that are out of this world, literally. If you are at all interested in space, astronomy, or astrophysics, then you will have the time of your life at the Adler Planetarium.

Finish your long weekend in Chicago at River North.

River North is the area just north of the Chicago River. Whoever named it wasn’t very creative, but they were very accurate.

River North is absolutely FULL of awesome bar and restaurant destinations. As with many neighborhoods in Chicago, the best way to experience it is by hopping from place to place. When you find a place you love, stay as long as you’d like, then move along to the next place! That is the Chicago way of experiencing the nightlife.

Chicago is an enormous place, sprawling for miles and miles. The downtown area has many neighborhoods, each of which has pros and cons for visitors to the Windy City.

The best places to stay for 3 days in Chicago are near the Chicago River, specifically River North, Gold Coast, Streeterville, and The Loop.

In addition to those, a few more great neighborhoods are Lakeview, Lincoln Park, West Loop (which is home to great Chicago street art ), Near North, and Old Town.

Here are a few great hotel recommendations for budget, mid-range, and luxury travelers.

Godfrey Hotel — The Godfrey Hotel is in the River North neighborhood, and is right in the middle of many of the best activities on your 3 day Chicago itinerary. On top of the great location, the hotel is beautiful on the inside and gets excellent reviews. The Godfrey Hotel is a wonderful place to hang your hat while exploring Chicago.

Check rates & book your stay at The Godfrey Hotel today!

Hyatt Regency Chicago — The Hyatt Regency Chicago is located in The Loop neighborhood, right on the Chicago River.

Many of the rooms in the Hyatt Regency have beautiful views of the Chicago River, the skyline, and the city streets.

The rooms are wonderful, the price is good, and the location is excellent. Additionally, the fitness center, meeting rooms, an on-site bar and restaurant, and access to Chicago activities make the Hyatt Regency one of the best places to stay in Chicago.

Check rates & book your stay at the Hyatt Regency Chicago today!

The Langham — Now, to the creme de la creme. If you’re a luxury traveler looking for the best hotel in Chicago, look no further than The Langham.

First off, the location could not be better. Located right on the Chicago River in River North, you’ll be within walking distance of nearly everything on your itinerary.

Additionally, The Langham pulls out all the stops when it comes to amenities. The on-site spa, fitness center, pool, and deluxe bar and restaurant are all five stars. Of course, the rooms are wonderful as well, and nearly all have stunning views of the cityscape.

Check rates & book your stay at The Langham today!

Chicago and food go hand in hand. You could explore a new food destination in Chicago every night for the rest of your life, and not eat at the same place twice. Not going to fact check that, but it is probably true. There are awesome restaurants on every corner, all across the city!

Here are four must-visit restaurants in Chicago that we love. 

Chicago-Style Pizza – Giordano’s

You can’t come to Chicago and not try some Chicago-style pizza. You literally can’t, it is impossible. The best Chicago-style pizza is at Giordano’s. The pizza here is absolutely LOADED with cheese and toppings, more than you have ever had, guaranteed. One slice and you’ll be satisfied, two slices and you’ll be stuffed. Be prepared to have leftovers!

Portillo’s is a Chicago institution. This started as The Dog House, a hot dog stand, and grew into Portillo’s, a delicious restaurant serving beef, burgers, and Chicago-style hot dogs all across the city. Portillo’s is yummy, quick, and is a Chicago must. Try the chocolate cake shake, you’ll be glad you did.

Happy Camper

Happy Camper is an excellent classic pizza place located in the Near North neighborhood, which offers an excellent atmosphere. This is a great place to watch sports, meet friends, enjoy a happy hour, and of course, try some pizza!

The toppings are creative at Happy Camper, and the pizza is DELICIOUS. There is also a huge selection of local and imported beers to try.

Girl and the Goat

Girl and the Goat is an absolutely EXCELLENT restaurant located in the West Loop neighborhood on Randolph Street. T he food here is delicious and is very creatively and expertly prepared.

Call ahead for a reservation at Girl and the Goat, as there may be a long wait if you just show up asking for a table. If you do just show up, however, this is worth the wait.

And you can walk across the street to one of the many bars on Randolph while you wait for a table at Girl and the Goat!

Bonus: take a Chicago food tour!

In a city as centered around food as Chicago, taking a food tour is one of the best ways to explore the city’s cuisine. 

Not only will you be able to sample a wide variety of classic dishes without committing to a whole portion, you’ll also learn plenty about Chicago’s history and culture along the way!

This popular food tour gets rave reviews and is an excellent addition to your long weekend in Chicago.

Book your food tour in Chicago today!

Getting around for 3 days in Chicago is in most ways easy, but can sometimes be challenging.

The public transport system is the easiest and most inexpensive way to get around, followed by cabs/Uber/Lyft, and finally driving yourself.

Much of the 3 days in Chicago itinerary laid out above, however, can all be completed by exploring on foot, especially from the recommended hotels. The awesome destinations and great parks are relatively close together and can be reached with a nice walk in the Chicago air.

Chicago has one of the best public transport systems in the US. The elevated train, AKA the ‘L’, brings people across Chicago east, west, north, and south. The ‘L’ stops at all of the amazing sites in the city, as well as O’Hare Airport, Midway Airport, and all the major thoroughfares.

If you would rather avoid public transportation, then the best way to travel around during this 3 day Chicago itinerary is with a cab/Uber/Lyft. Traveling this way is likely the fastest if you can avoid rush hour, and the most convenient. However, it will be more expensive than using the ‘L’ trains.

Finally, you, of course, have the option of driving yourself around town. In our opinion, this is the most stressful way to get around, as you’ll have to worry about parking in the busy downtown streets. This is a challenge and is made worse considering that many hotels offer parking fees.

The best time to plan a long weekend in Chicago is during the summer. The weather during the summer is absolutely perfect, and it’s definitely the easiest time to pack light for a Chicago vacation (if you visit during the blustery winter, be sure to carefully consider what to wear in Chicago !). This is also the best time to explore the awesome parks, beaches, and outdoor destinations in the Windy City.

Each year in the summer, Lollapalooza brings huge crowds looking for an awesome time and great music. Lollapalooza draws many of the best music acts in the world, so traveling to Chicago during the music festival is a great opportunity. On top of this festival, many great music artists perform regularly at Wrigley Field, Soldier Field, the United Center, and the other great venues across Chicago.

Coming in a close second to the Chicago summer is the spring when the city defrosts after its long Chicago winter and comes alive. There is nothing quite like spending 3 days in Chicago when the atmosphere is on the rise, as it is in spring.

Also during this time is St. Patrick’s Day, one of the largest holidays in Chicago. On St. Patrick’s Day the river is dyed bright green, and the partygoers are out in force.

4 thoughts on “3 Days in Chicago: The Ultimate Weekend in Chicago Itinerary”

I’d like to follow for future information

Thanks for this comprehensive guide! It made planning a trip to Chicago so much easier!

As a frequent traveler to Chicago, who lives just a few hours away, I want to mention a few places that truly make Chicago iconic. The Palmer House Hotel is the best in the City. Right outside the doors of the Palmer House is a Chicago favorite, with a long history, called Miller’s Pub. Grab an Allagash White beer on tap – a local favorite. Don’t miss a food tour of Chinatown. There is so much history there, and the food is really amazing! Other amazing foodie spots in Chicago are Bongo Room for brunch and Cafe Babareba for Spanish style tapas (do not miss the baked goat cheese in tomato sauce). An architectural tour on the Chicago River is a lovely way to spend the day and if that isn’t your thing, the water taxis are a fun way to get around.

Agrred with the other poster–This itinerary is hugely missing the architecture tours! Best thing to do in the city. River north is fine, but kind bro-y for lack of a better descriptor. Bongo room is in Wicker Park which I describe as our Williamsburg. Not quite as artsy and cool as it was 5 years ago but still very fun!

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The 25 best weekend getaways from Chicago

Eat, play and explore a different city (without venturing too far) by booking an amazing weekend getaway from Chicago.

Although we adore our city’s endless restaurants , museums  and attractions , a change of scenery is always nice.  Luckily for us, the Midwest has plenty to offer with exciting destinations only a few hours’ drive from Chicago. You can lounge in transparent waters and hike sand dunes in the “Malibu of the Midwest,” recharge at a bed and breakfast on a farm surrounded by friendly sheep, and marvel at modernist architecture in a small southern Indiana town. Many of these places are also great for a day trip  or family-friendly getaway . So if you're looking to skip town, here are the best weekend getaways from Chicago.

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Top weekend getaways from Chicago

1.  Milwaukee, WI

Driving time from Chicago:  One and a half hours

Our neighbors to the north will make you feel right at home with a seemingly endless supply of craft beer and cheese. Leave time to explore world-class cultural institutions before hopping on the Amtrak for a stress-free ride back to Chicago.

Do this:  Start your day at the Milwaukee Art Museum , an architectural masterpiece along the shores of Lake Michigan that houses almost 25,000 works of art. Quite honestly, the building itself—designed by Spanish architect  Santiago Calatrava— is a masterpiece in its own right, even if you don't want to splurge on admission.

Stay here: Sleep in the heart of the city   when you check into the Kimpton Journeyman Hotel in Milwaukee's Third Ward. Located within walking distance of some of the city's best restaurants and bars, this beautiful boutique hotel also has a jaw-dropping rooftop terrace and rooms that are outfitted with lavish touches—perfect for a weekend away.

2.  Kohler, WI

Driving time from Chicago: Two hours and 15 minutes 

New York City’s Central Park architect Frederick Law Olmsted left his legacy in several places in the Midwest, including rural Wisconsin when the Kohler Company commissioned him in the early 1900s to design its new planned “industrial garden community” five miles west of Sheboyan. Today, this community of 2,000 is ideal for unplugging. 

Do this: Climb the dunes at Kohler-Andrae State Park before indulging in a spa service at Kohler Waters Sp a , the only five-star spa in the Midwest. After your treatment, take advantage of the hydrotherapy circuit, a combination of cold plunges, steam room and sauna visits, and a relaxation pool.

Stay here: Splurge on one of the three Destination Kohler lodging options—a luxury resort, a lakeside inn or one of the cabins—or opt for the more moderately priced and equally exciting  Velvet Sheep Farms Bed & Breakfast and Fiber Farm , just a ten minute drive north of Kohler. Embrace the slower pace of life as you get to know the farm’s beloved sheep by name and take a tour of their fiber production facilities.

3.  Galena, IL

Driving time from Chicago:  Three hours

A charming, small Illinois town known for its history, 19th-century architecture and resorts. 

Do this: Make your way through over a hundred shops and boutiques in the downtown area. History buffs can head over to the Ulysses S. Grant Home  to tour the city’s proudest attraction. Once you’ve worked up an appetite, stop into Log Cabin Steakhouse , which has been in operation since 1937. During the third weekend of June, tourists and locals alike gather for the annual Great Galena Balloon Race .

Stay here: The 6,800-acre Eagle Ridge Resort & Spa has everything you could need for a relaxing vacation. Play a round of golf on any of the four courses (there are 63 holes in total), book a spa treatment or go for a swim. The resort also offers 22 miles of hiking and biking trails, three restaurants on site and lodge-style rooms outfitted with jacuzzi bathtubs.

4.  Indianapolis, IN

Driving time from Chicago: Three hours 

Indianapolis’s nickname may be “Naptown,” but there’s nothing sleepy about the locally-owned and farm-to-table restaurants, busting jazz clubs, bookstores and quirky gift shops found around Indy. Fanning out from Monumental Circle, the heart of downtown Indy, Indianapolis’s neighborhoods are home to a friendly and welcoming cultural scene.

Do this:  Spend your time browsing the stores, spotting art (and fairy homes!) and eating in the Fountain Square Cultural District, a diverse and LGBTQ+ friendly neighborhood just south of downtown. By day, make time for coffee and snuggles at Nine Lives Cat Cafe and at night, see a drag show at White Rabbit Cabaret or coincide your visit with swing dancing at the historic Fountain Square Theater Building, a longstanding Indy tradition. 

Stay here: Housed in the restored art-deco architecture of a former Coca Cola Bottling Plant, Indy’s Bottleworks Hotel was used by Indianapolis Public Schools for years before becoming one the city’s most unique luxury accommodations. The Bottleworks grounds also includes a food hall and several small businesses.

5.  Madison, WI

Driving time from Chicago: Two and a half hours

Life in “Lake City,” as Wisconsin’s second largest city is often referred to, is undeniably beautiful—and full of year-round water-focused recreation. Between the parks and shorelines of lakes Mendota, Monona, Waubesa, Kegonsa and Wingra, visitors can expect to be in close proximity to nature and green living. In fact, wherever you live in Madison, you’re no further than 10 minutes from a park. 

Do this: Spend a day at Olbrich Park along the shores of Lake Monona. In the summer, rent a kayak, canoe, or stand-up paddle to relax on the water, and in the winter, opt for snowshoes and remind yourself there’s no bad weather—only bad clothing. After, head to Giant Jones Brewery , one of the best boozy destinations from Chicago . 

Stay here: One of Madison’s newest hotels is the centrally-located boutique Hotel Indigo Madison Downtown , housed in the former Mautz Company Paint Building. It’s a short walk from Giant Jones. And as far as we’ve heard, the fumes are gone.

6.  Door County, WI

Driving time from Chicago:  Four and a half hours

The 300 miles of shoreline separating Green Bay and Lake Michigan offers vacationers a mix of natural beauty, history and locally sourced food.

Do this: Start with breakfast at Blue Horse Cafe , where you can dig into eggy breakfast sandwiches and delightful baked goods. That should provide you with the energy for hiking on the Ice Age National Scenic Trail, which features dramatic landscapes carved by glaciers 12,000 years ago.

Stay here: Historic bed and breakfast White Gull Inn   is a quaint experience that dates all the way back to 1896. All of the rooms have been meticulously restored with modern amenities through the years, ensuring guests get a comfortable night’s rest. In the morning, wake up to French toast stuffed with Wisconsin cream cheese and Door County cherries, served with Door County maple syrup.

7.  Detroit, MI

Driving time from Chicago: Four and a half hours

The renaissance of Detroit has brought with it a vibrant downtown area, oodles of amazing restaurants and bars and several destination-worthy boutique hotels—all the makings of a weekend trip away.

Do this: Plan your visit around award-winning restaurants like Selden Standard and Sister Pie . Between bites, hit up John K. King Used & Rare Books , a four-floor emporium of old tomes, as well as Belle Isle Aquarium along the Detroit River.

Stay here: Book an affordable room at the Siren Hotel , a 106-room property in the historic Wurlitzer Building. You don't have to go far for a great cocktail—downstairs watering hole, the Candy Bar , serves funky creations in an all-pink, chandelier-adorned room.

8.  Des Moines, IA

Driving time from Chicago: Five  hours

Iowa’s capital city doesn’t get the love it deserves, but you’ll find plenty to do in a weekend, with tons of art, food and breweries and a packed summer calendar of local events and festivals. 

Do this: There’s a lot of beauty in Des Moines, including at the sprawling indoor-outdoor Greater Des Moines Botanical Garden , and the six-mile  Art Route  connecting more than 80 pieces of public art. Plan your trip around one of the city’s many massive summer festivals, like the packed indie music celebration 80/35 , the inspiring Des Moines Arts Festival and Interrobang Film Festival, and—you guessed it—the Iowa State Fair . 

Stay here: For luxe accommodations, it’s hard to beat the  Surety Hotel , featuring modern rooms and the elegant Mulberry Street Tavern downstairs. Grab a martini at the bar at the punnily-named Des Lux Hotel before an evening on the town, or just curl up in your room with a fireplace. 

9.  Traverse City, MI

Driving time from Chicago: Four hours and 50 minutes 

Situated in Grand Traverse Bay’s 180 miles of Lake Michigan shoreline, Traverse City is a small town with arts, culture, water recreation and summer street festivals. There's also easy access to the Old Mission Peninsula, Leelanau Peninsula, Sleeping Bear Dunes and the strings of other small towns dotting the pastures and hills of what Michiganders call “Up North.” 

Do this: Meander by car or bike around the wineries of Leelanau Peninsula Wine Trail. Featuring over 20 award-winning Michigan wineries, you’ll pass rolling hills with views of Lake Michigan. Stop for lunch at  the tranquil Farm Club for a selection of al dente pastas, local meats, pan-seared vegetables and leafy salads straight from the garden.

Stay here: Cozy up in one of the six rooms at downtown boutique hotel The Flats and Iron + Union . The 1890s-era building housed many beloved local businesses throughout the past century and is now a prime location for visitors.

10.  Louisville, KY

Driving time from Chicago: Four hours and 45 minutes

Kentucky’s largest city, just across the Ohio River from southern Indiana, is steeped in bourbon and long on charm.

Do this:  The home of the old-fashioned and the mint julep embraces its role as the gateway to Bourbon Country. The city has a number of tourable distilleries, including Evan Williams , Angel’s Envy and Old Forester .

Stay here:  True to its name, 21c Museum Hotel is part boutique hotel, part contemporary art locale. With more than 75,000 square feet of exhibition space, there's bound to be something for everyone. The hotel is also home to one of Louisville’s finest restaurants, Proof on Main , where chefs craft Southern fare using seasonal ingredients sourced from the Ohio River Valley. 

11.  Ann Arbor, MI

Driving time from Chicago: Four hours

Situated just west of Detroit, Ann Arbor is home to University of Michigan, a slew of breweries and a handful of phenomenal restaurants. If you’re a roaming foodie or beer nerd, this is the low-key vacation spot you’ve been searching for.

Do this:  You’ll want to make it a point to visit Spencer , an exquisite neighborhood spot that offers pastries and coffee in the morning and a selection of seasonal small plates, cheese and wine when the sun goes down.

Stay here: Graduate Hotels  is a collection of boutique properties that celebrate the youthful feel of college days past, and Ann Arbor is one of the group’s many locations in the country. The space is outfitted in Persian rugs, plaid chairs, velvet couches, reclaimed wood and gorgeous chandeliers. Think of it as the prep school of hotels.

12.  St. Louis, MO

If you only know the big Arch, Busch Stadium and deep-fried ravioli, we assure you there’s a lot more of STL to explore. 

Do this: Like Chicago, one of the best ways to get to know St. Louis is by visiting its neighborhoods—browse local makers and antiquers on Cherokee Street , explore a host of breweries like Side Project and Schlafly , and savor a traditional red-sauce meal on The Hill. The 1,300-acre Forest Park , one of the most stunning urban green spaces in the country, is a must. If you’re traveling with kids (or kids at heart), don’t miss the interactive, immersive City Museum , an educational playground with slides, sculptures you can play on and even vintage pinball machines. 

Stay here: The art deco Royal Sonesta Chase Park Plaza St. Louis   offers views of Forest Park and renovated guest rooms in the popular Central West End. The quirky Moonrise Hotel on the Delmar Loop leans into the lunar theme and offers an enticing all-seasons rooftop bar. 

13.  Peoria, IL

Once a small riverfront European settlement in early Illinois history, Peoria is now a safe haven for the Midwest LGBTQ+ community looking for affordable housing. Plan a visit during the River City Pride Festival to support local LGBTQ+ artists and vendors and enjoy arts, culture and food.

Do this: Drive the two and a half mile scenic Grand View Drive , one that Theodore Roosevelt famously reported was the “Most Beautiful Drive in the World.” The panoramic views of the Illinois River are stunning no matter the season, but visitors flock to Peoria for fall foliage spotting.  

Stay here: There are plenty of small, historic bed and breakfasts in and around Peoria, but for a unique experience, opt to stay 20 minutes west of downtown Peoria at Wildlife Prairie Park’ s converted Santa Fe train caboose or old grain bin.

14.  Eau Claire, WI

Driving time from Chicago: Five hours

You’ve been to Madison and Milwaukee, but a trip to the Chippewa Valley in northern Wisconsin is an experience unto itself. You’ll find rolling hills and colorful foliage, plus plenty of beer and cheese to smuggle back to Chicago.

Do this:  Hiking is nice and all, but if you really want to see what autumn looks like here, hit the Chippewa River. Head to Riverside Bike & Skate in downtown Eau Claire, where you can rent kayaks and hire a shuttle service to drive you upstream.

Stay here:  Bon Iver frontman and Eau Claire native Justin Vernon is one of the partners behind the Oxbow Hotel , so it’s no surprise that it’s easily the trendiest joint in town. The renovated motel has its own bar and restaurant, and each room contains a turntable. You probably won’t write a hit indie-rock album in your room, but at least you can listen to one.

15.  Iowa City, IA

Driving time from Chicago: Three and a half hours

Nothing says fall like holing up in a college town and reminiscing about football tailgating, dorm food and campus crushes.

Do this: Starting in September, the walkable University of Iowa campus turns into a postcard-worthy scene that spans from the downtown pedestrian mall to the darling surrounding neighborhoods. Start your self-guided tour in the epicenter of it all, the Pentacrest, where four buildings on the campus surround the Old Capitol Museum.

Stay here: Bunk up at the super-modern Hotel Chauncey , which has 51 spacious suites outfitted with sleek furniture, floor-to-ceiling windows and minimalistic accents. Toss in a rooftop deck, gym and in-room kitchens, and it’s no wonder this place books up early during football season.

16.  St. Joseph, MI

Driving time from Chicago:  One hour and 45 minutes

This Michigan beach town and its twin city Benton Harbor offer picturesque sandy shores, as well as plenty of wine.

Do this: Soaking up the sun on beaches is the most obvious attraction, but once you’ve gotten your fill of vitamin D, hit up the nearby Lake Michigan Shore Wine Trail . It’ll take you to wineries up and down the coast, and you can easily spend an entire weekend just swirling, sniffing and sipping.

Stay here: Located along the St. Joseph River, the Inn at Harbor Shores boasts waterfront views and amenities like a spa and a golf course that’s close by. If you don’t feel like leaving the hotel, grab a seat on the patio of the in-house restaurant, Plank’s Tavern on the Water , for a relaxing meal.

17.  Spring Green, WI

Quiet and quaint, it’s easy to see why the scenic village of Spring Green on the Wisconsin River attracted the likes of Frank Lloyd Wright, who made his summer home here at the must-see Taliesin.

Do this:  Get weird and head to the House on the Rock , a curious wonderland of oddities and artifacts that’s set quite literally on a giant rock surrounded by panoramic views of towering trees. Don’t miss the massive indoor carousel or the Infinity Room, an engineering wonder with 3,264 windows that juts out 218 feet over the valley.

Stay here:  Step back in time at Spring Valley Inn , designed by the Frank Lloyd Wright School of Architecture. The small inn on 10 acres of wooded prairie offers unbeatable views of the valley, plus a relaxing bar, patio, fire pit, indoor pool, hot tub and workout room.

18.  Bloomington, IN

This next-level college town has all the big-city amenities you crave, but it’s tucked in the middle of hills, forests and nearby lakes. 

Do this:  Fill up at the intimate Feast Market and Cellar , a family-owned kitchen with a lovely corner porch. The restaurant makes everything from scratch daily, so you know you’re consuming fresh eats, from the mayonnaise to the bread to the macarons.

Stay here: Grant Street Inn , which is within walking distance of downtown and the attractive Indiana University campus, has four-star hotel accommodations with bed-and-breakfast charm. Choose from the main house, built in the 1890s, or any of the other four buildings, each with unique themes and features, from those done up in traditional antique decor to the newest space, a LEED-certified addition.

19.  Toledo, OH

Once a popular stop on the railway line between Chicago and New York, Toledo is still worth a visit, full of Great Lakes history, native greenery and other surprises.

Do this:  Toledo is a paradise for flâneurs—wander the Old West End to take in beautiful Victorian homes that line the peaceful streets, or take a nice, pastoral break in the Swan Creek Preserve . The National Museum of the Great Lakes   offers a fascinating look at the region's history. For a livelier evening, take in some minor league baseball with the Toledo Mud Hens .

Stay here:  Get a room with a view of Lake Erie at the Maumee Bay Lodge , located amid 1,336 acres of natural splendor in Maumee Bay State Park. When you’re not enjoying the private balconies and patios, grab food from the Lodge’s restaurant, hit the links at an 18-hole golf course or go for a hike on a nearby trail.

20.  Fort Wayne, IN

Driving time from Chicago: Three hours

Indiana’s second largest city was once a booming industrial hub with more than 300 churches. But make no mistake—there’s no shortage of small-town charm and plenty of places to let loose.

Do this: Spend an afternoon at Promenade Park where locals congregate on the riverfront for festivals, picnics and water recreation. Grab pizza and beer from local favorite Pint & Slice and don’t miss the photo opportunities in front of murals in the alley.

Stay here: Located in the heart of downtown, The Bradley   is a 124-room, nine-suite boutique hotel featuring murals and decor from local artists. Get great views of the city from the hotel’s rooftop bar, Birdie’s .

21.  Dubuque, IA

This historic Mississippi River settlement’s attraction goes far beyond a visit to the Field of Dreams. It’s easy to get lost in the vivid murals, craft breweries and outdoor art galleries.

Do this: What’s a weekend getaway without a ride up the world’s shortest and steepest scenic railway? Head to Fenelon Place Elevator Co for a 189-foot trip from Fourth Street to Fenelon Place, where you can take in an aerial view of the city.

Stay here:  The century-old Hotel Julien Dubuque  is full of elegance, blending modern luxury with historic charm. It offers 133 rooms and amenities like an indoor pool, spa and fitness center.

22.  Carbondale, IL

This Southern Illinois university town was developed as a result of the railroad, but today is a great jumping off point for exploring Shawnee National Forest and nearby wineries.

Do this: With Carbondale as your home base, take your time exploring the 11 wineries that make up the 40-mile Shawnee Hill Wine Trail . Between wineries, pick up one of The Iron Whisk’s famous Dutch babies (a puffy pancake made in a cast iron pan) from a converted auto garage kitchen in Cobden.

Stay here: Referencing Carbondale’s past as a railroad destination, the  Train Inn is a four-room bed and breakfast in a renovated early 1900s bungalow featuring art deco styling and train memorabilia. Owner Paul Lewers will make your breakfast according to any dietary preferences, but he encourages those willing to venture outside their typical palate to try his red-eye gravy, a speciality made from country ham and coffee.

23.  Columbus, IN

In the heart of Southern Indiana, Columbus is an unexpected center for boundary-pushing architecture—in fact, the American Institute of Architects ranked the city sixth in the nation for architectural innovation.

Do this: Take an Architectural Highlights Tour  of more than 30 of Columbus' structures and learn how this city became the state's award-winning arts and design destination. Once you’ve worked up an appetite, stop by Columbus Bar , the oldest bar and restaurant in town.

Stay here:  Columbus’  Hotel Indigo is a perfect place for architecture- and design-lovers to rest their heads, outfitted with an in-house gallery featuring pieces by regional artists.

24.  Davenport, Iowa

Driving time from Chicago: Two and a half hours

You’ve tried Quad Cities-style pizza, but now it’s time to explore Davenport’s museums, gardens, parks and charming riverfront.

Do this: Glimpse permanent and rotating exhibitions of international and regional works at the Figge Art Museum situated downtown just blocks from the river. Then, make you way to the German American Heritage Center to learn about German immigration and culture—and why some consider Davenport to be the most German city in the U.S. Stay here: Built on the site of Davenport’s first hotel, the city’s industrial and agriculture roots mingle with modern art and design at The Current Iowa , decorated with split canvas photographs of freight cars and colorful paintings of pastoral scenes. Sip the hotel’s namesake cocktail with gin, elderflower, lavender and mint and relax at the  UP Skybar as you watch the sun set over the river.

25.  Kalamazoo, MI

Western Michigan boasts spectacular fall foliage and, in turn, excellent apple-picking conditions. Make Kalamazoo your home base for an excursion and reap the benefits of the lively Midwestern town.

Do this: Husted's Farm Market & Cider Mill is one of several autumnal havens in the region, featuring fresh, pickable produce June through October. When the asparagus, rhubarb and strawberries are gone, you’ll find pumpkins, apples (23 varieties) and gourds in their place.

Stay here:  Enjoy the royal treatment at the Henderson Castle Inn , a bed-and-breakfast in a historic 19th-century mansion. The inn features 12 ornate rooms, spa amenities, a steakhouse, a craft cocktail lounge and high-tea service.

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Hit the road on these easy day trips from Chicago, where affordable fun awaits busy city dwellers

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

Weekend In Chicago: An Epic 3 Days In Chicago Itinerary

August 16, 2022 by //  by  Midwest Explored Leave a Comment

If you’re planning to spend a weekend in Chicago, then you’ve come to the right place!

Chicago is the biggest city in Illinois and it’s easily one of the most vibrant cities in the Midwest too!

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.)

You can explore Chicago in a few days , but I suggest planning a fun weekend trip to Chicago if you have the time!

On this Chicago itinerary, I’ve made sure to include all of the top sites in Chicago as well as a few more unique activities.

Each of these 3 days in Chicago is packed with fun things to do in Chicago that you won’t want to miss.

Plan to spend all day, into the night, exploring! Chicago, like New York City, is a city that never really sleeps.

That means you’ll find things to do well into the night in Chicago, and they’re definitely worth the late bedtime.

I’ve also made sure to include my favorite tips on how to plan a trip to Chicago, like the CityPass.

If you plan to visit a lot of the museums or popular attractions in Chicago that require tickets, you may want to consider getting a Chicago City Pass !

At the end of this Chicago itinerary, you’ll feel prepared to plan the ultimate weekend in Chicago.

So, let’s take a look at my Chicago tips and itinerary for Chicago to help you have a fun weekend trip to Chicago!

Getting To Chicago

It’s really easy to get to Chicago from pretty much anywhere.

If you’re planning to fly into the city, you’ll want to use Chicago Midway International Airport.

Because it’s an international airport, there are direct flights from all over the country.

You can also fly right into the city if you’re traveling from around the world too.

For those who are planning to drive to Chicago, you can do that too.

This is an especially good option if you are planning to extend your trip to explore some of the best day trips from Chicago .

Chicago is easily reached from several highways, so you’ll be able to get there by car or bus.

The city also has several train stations if you prefer to travel by rail.

Getting Around During Your Chicago Weekend Getaway

Chicago’s streets are organized by a grid system, similar to New York City.

So, it’s really easy to get around the city and not get lost.

It’s also a very walkable city, and on this itinerary for Chicago, you’ll be able to walk to just about every stop. However, if you don’t want to walk the enter weekend in Chicago, don’t worry.

Chicago has a great public transit system that includes buses, the subway, and taxis. In fact, it’s the second largest public transportation system in the US.

You can also use ride-share programs or rent bikes to ride around the city. Or you can get tickets for the Hop-On Hop-Off Bus in Chicago .

There’s even a water taxi that you can ride to get around the city!

No matter how you choose to travel around, you’ll find it’s very easy to explore Chicago.

Book Your Hop-On Hop-Off Bus Tickets Here: Getyourguide.com

The Ultimate 3-Day Weekend In Chicago Itinerary

Day 1: iconic chicago.

For the first day of your 3 days in Chicago, I suggest seeing some of the most iconic sites in Chicago.

You’ll see some of the oldest buildings and areas in the city along with some newer Chicago icons.

This first day is very walkable although most of the walks are about 20-minutes long.

But, you’ll only need to drive or get public transportation towards the very end of the day.

Stop 1: Window Shop At Chicago’s Magnificent Mile

Start your day with a walk around the Magnificent Mile .

The Magnificent Mile is the nickname that’s been given to the northern end of Michigan Avenue.

That’s because it’s full to the brim with luxury shops, restaurants, and boutiques.

Even if you can’t afford to purchase anything from some of these stores, it’s still a really cool thing to do during your Chicago weekend trip.

The area is pretty iconic and it’s one of the things most people want to at least experience during their first time in Chicago.

But even if it’s your twentieth time in Chicago, it’s still fun to walk along the Magnificent Mile.

The front of the shops and restaurants are always elaborately decorated, especially if you’re visiting Chicago during Christmas !

It’s also where you’ll find some of the tallest skyscrapers in the city.

Book Your Chicago Loop Tour Here: Magnificent Mile.

Stop 2: The Navy Pier Is A Must-See Attraction During A Weekend In Chicago

After exploring the Magnificent Mile, you’ll walk about 20-minutes to your next destination, which is the Navy Pier.

The Navy Pier is a huge pier located on the shoreline of Lake Michigan.

There, you’ll find even more things to do in Chicago in a weekend.

The pier has shops, restaurants, and amusement park-style rides.

You can see the city and the lake from the top of the Centennial Ferris Wheel , or spend some time playing games in the pier’s arcade.

During summer nights in Chicago , the Navy Pier has a fireworks show every Wednesday night.

The Navy Pier is a ton of fun during the day, but if you want to see it at night, it’s great too.

Book Here: Centennial Ferris Wheel

Stop 3: Enjoy Beautiful Views Of The City On The Chicago Riverwalk

Next, you’ll head to the Chicago Riverwalk for a walk.

The general starting point of the Chicago Riverwalk is about a 20-minute walk away from the Navy Pier.

However, there are several different entrances to the Riverwalk along the path that you can use to access it.

The Chicago Riverwalk is a pedestrian path that is right alongside the Chicago River.

While you walk, you’ll be able to get some incredible views of the city.

There are also restaurants, small shops, and areas where you can just sit and enjoy the view.

So, if you need a break from walking, you’ll find plenty of spots to rest at this stop on this Chicago itinerary.

Book Your Tickets: Self-Guided Riverwalk Tour

Stop 4: Learn More About Chicago’s History At The Chicago Cultural Center

After spending some time on the Chicago Riverwalk, head to the next stop on this itinerary for Chicago in a weekend.

Your next stop is The Chicago Cultural Center and it’s just over 15-minutes away from parts of the Riverwalk.

The Chicago Cultural Center originally opened in 1897 as the central library building.

Today, it’s where the Mayor of Chicago welcomes visitors like the President of the United States and foreign dignitaries.

When the Mayor isn’t greeting guests, the space is used to house a revolving schedule of unique exhibits.

You can also take tours to learn more about the history of the building itself and its incredible architecture.

It’s open daily from 10 am to 5 pm, so it’s the perfect last stop before you find somewhere to have dinner.

Book Your Tickets: Gilded Age Architecture Walking Tour

Stop 5: Take A Break From Walking While You Enjoy The Open-Top Panoramic Bus Night Tour

After dinner, you’re probably going to want to take a break from all the walking you’ve done on your first of 3 days in Chicago.

However, there are still tons of fun things to do in Chicago in a weekend.

So, I suggest taking one of the Open-top Panoramic Bus night tours .

These buses are completely open on the top level, so on a beautiful night, it’s a great activity.

As you ride around on the bus, you’ll have an expert guide telling you about the different historic buildings you’ll pass.

It’s also a great way to see the city all lit up at night.

While you rest your feet, you’ll get a great tour of the city, and even learn something new.

Book Your Tickets: Panoramic Night Bus Tour

Stop 6: End The Night With Drinks And Live Music At The Green Mill During Your First Of 3 Days In Chicago

Now that you’re rested up a bit, head to your last stop of the night.

For this last stop, you’ll most likely need to take public transportation or get a ride to reach it.

However, it’s totally worth it.

The Green Mill is an iconic jazz bar in Chicago and it’s one of the best things to do in Chicago at night.

If it’s your first time in Chicago, you’ll definitely want to make a trip out to The Green Mill.

They play live music daily, and they also have a full bar.

One thing to keep in mind though is that The Green Mill is strictly cash only. So make sure you stop by the ATM before you get there.

Book Tickets Here: Chicago Food Tour

Day 2: Explore The Heart Of Chicago

For day 2 of your 3 days in Chicago, you’ll be staying in the heart of the city.

Everything on this day of the itinerary for Chicago is really close to each other.

In fact, some of the stops are less than a 10-minute walk away.

You won’t need a car or public transportation at all to enjoy your second day during your weekend in Chicago.

There are so many things to do in Chicago, so let’s get going!!

Stop 1: Explore Millennium Park

Start your second day during your weekend in Chicago exploring Millennium Park .

Millennium Park is probably one of the most popular, if not the most popular, attractions in Chicago.

Each year, the park sees an average of 25 million visitors.

Part of that is because the park is beautiful and because most of the things to do within the massive park are free.

It’s an absolutely massive park that is over 24 acres total and it’s full of a variety of attractions.

In fact, you’ll spend most of day 2 just exploring the different attractions in Millennium Park and the attached Grant Park.

So, that’s where you’ll start the day, to give yourself plenty of time to explore.

Most of the heart of downtown Chicago is situated around Millennium Park.

This makes it easy to exit the park and find a great restaurant or shop and then go back in to explore again.

Book Your Tickets: Millenium Park Self-Guided Tour

Stop 2: See Cloud Gate, Or ‘The Bean’

You probably know about ‘The Bean’, a pretty popular sculpture in Millennium Park .

While it’s known as ‘The Bean’, the sculpture’s actual name is Cloud Gate.

When you get to Millennium Park, after exploring the entrance area of the beautiful park, I suggest heading to Cloud Gate.

Cloud Gate can be found just 400 feet away from the entrance to Millennium Park.

So, you really can’t miss it and if it’s your first time in Chicago, you’ll definitely want to stop by for a picture.

After you get your pictures and admire Cloud Gate, head to your next stop on this itinerary in Chicago.

Book Tickets: Self-Guided Millennium Park Tour

Stop 3: Admire The Artwork At The The Art Institute Of Chicago

Just a short walk away from Cloud Gate, and just outside of Millennium Park is the Art Institute of Chicago .

The Art Institute of Chicago is one of the best things to do during a weekend getaway in Chicago, especially if you’re an art lover.

It’s been voted ‘Downtown Chicago’s #1 Museum’ for a reason!

The museum is open Friday through Monday, from 11 am to 5 pm, and on Thursdays from 11 am to 8 pm.

You’ll need to purchase entrance tickets in advance, and for non-Chicago residents, they are $25 per adult.

Inside the museum, you’ll find artworks by famous artists like Cezzane, van Gogh, Joan Mitchell, Picasso, Monet, Renoir, and de Kooning.

The bulk of their collection is art pieces from Impressionist, Modernist, and Post-Modernist art movements.

However, they also have an extensive collection of historic world art from Mexico, Japan, Egypt, and India.

Make sure to plan to spend plenty of time exploring this amazing Chicago itinerary stop.

Book Tickets Here: Art Institute of Chicago

Stop 4: See The Light Show At The Buckingham Fountain

From the Art Institute, take a short 10-minute walk to Grant Park and the Buckingham Fountain.

The Buckingham Fountain puts on a water show daily, from 9 am to 11 pm, from May to October.

You can catch the show every hour, and it lasts about 20 minutes.

At dusk, the water show turns into a water and light show.

You can see the light show all throughout the night. The last light show starts at 10:35 pm.

That means you have plenty of time to make it to this stop.

You can head to the Buckingham Fountain before dinner, but it also makes for a great after-dinner activity.

Especially if you want to catch the light show too.

Book Tickets: Chicago Night Tour

Stop 5: Go On A Walking Gangsters And Ghosts Tour During Your Weekend In Chicago

A great way to end the second day of your 3 days in Chicago is with a gangsters and ghost tour .

Chicago has a unique history, thanks to the gangsters and bootleggers that called the city home in the early 20th century.

If you want to learn more about this history and look for ghosts at the same time, then this is a super fun weekend trip to Chicago activity.

There are a variety of companies that offer ghost tours throughout the city.

Most of them are walking tours, but there are a few companies that have bus tours as well.

You’ll walk the historic city loop, and based on historical details, learn all about the seedy Chicago underbelly and the ghosts that now haunt the city.

It’s a fun way to end the day and you’ll learn some really cool historical facts too!

Book Tickets: Gangsters and Ghosts Tour

Day 3: Explore The Chicago Skies And The City’s Science Museums

For your last day in Chicago, you’ll be exploring the Chicago skies and some of the best science attractions in the city.

While you can walk to most of these attractions, I suggest using Chicago’s massive public transit system to get around for your last day of 3 days in Chicago.

Plus, your feet are probably pretty tired from your first two days!

Stop 1: See The Views From The Skydeck Chicago And The Willis Tower

Start the last day of your weekend getaway in Chicago at the Skydeck Chicago and Willis Tower .

The Willis Tower was originally known as the Sears Tower, until 2009 when it was renamed.

What makes the Willis Tower so cool is that it’s one of the tallest buildings in the world and it’s the second-tallest building in the US.

It is 1,450 feet high and is 110 stories. At the top of the Willis Tower is the Skydeck Chicago.

The Skydeck Chicago has 360-degree views of the city and a clear skybox that you can walk out onto.

You’ll be able to see the ground below you through the clear floor as well as the full city skyline.

It’s a really cool activity when you’re visiting Chicago for a weekend.

Book Here: Willis Tower Skydeck & The Ledge Tickets

Stop 2: Learn About Space At The Adler Planetarium

From Willis Tower, head to the Adler Planetarium.

The Adler Planetarium is a 45-minute walk away, so you’ll probably want to use public transit to get there.

It is a public museum that is open daily from 9 am to 4 pm. However, on Wednesday, the museum is open late until 10 pm.

Entry to the museum is $19 per adult and includes a wide variety of exhibitions.

You can also choose to add planetarium shows to your ticket, for an additional fee.

Exhibits include images of the Chicago night sky, artifacts from the moon landing and the Mar’s Rover, and tons more.

You’ll want to give yourself plenty of time exploring the Adler Planetarium before you head to your next stop on this Chicago itinerary.

Book Tickets: Eastside Chicago City Exploration Game

Stop 3: Explore The Field Museum Of Natural History

The Field Museum of Natural History is just a short 10-minute walk away from the Adler Planetarium.

It’s a natural history museum, and is actually one of the biggest natural history museums in the world!

For adults, general admission to this cool Chicago museum starts at $29.

You can also add tickets to the various shows and special exhibits the museum hosts as well.

The Field Museum is open daily from 9 am to 4 pm.

Included in the general admission ticket are several unique exhibits.

You can see the Granger Hall of Gems, step inside the Pawnee Earth Lodge, or meet Sue the T-Rex!

Outside of the museum, there is also a large native plant garden that you can stroll through.

Before you head to the next Chicago itinerary stop, you may want to grab a bite to eat. There are food carts near the museum and some great restaurants nearby too.

Tickets Here: Field Museum Of Natural History

Stop 4: Visit The Chicago Museum Of Science And Industry

After you are done exploring the Field Museum, head to the Chicago Museum of Science and Industry.

You’ll want to take public transit to get to The Chicago Museum of Science and Industry from the Field Museum.

The museum is open daily from 9:30 am to 5:30 pm and tickets for adults are $21.95 each.

If you want to see some of the special exhibits, you’ll need to add a ticket to the general admission ticket. But they are always very cool and definitely worth the extra cost.

The exhibits that are included with general admission are super cool too, so you don’t have to see any of the special exhibits to enjoy the museum.

While you’re there, you can explore a German U-boat submarine, learn about tornadoes and avalanches, or step into a fairy castle.

You’ll want to give yourself plenty of time to explore this fun museum on your last of 3 days in Chicago.

Stop 5: Have A Romantic Dinner On A Chicago River Cruise

This next stop on your Chicago itinerary is a great date night in Chicago option if you’re on a couples trip to Chicago.

There are a few different companies that offer romantic sunset dinner cruises on the Chicago River.

As you sail along the river, you’ll get to enjoy a delicious dinner as well as some stunning views of the city skyline.

Some of the cruises also include live music and drinks along with dinner.

If you choose a cruise that doesn’t, don’t worry. Your last stop during your weekend in Chicago includes drinks and stunning views!

Tickets Here: Romantic Sunset Cruise

Stop 6: Drinks At A Rooftop Bar

Your weekend in Chicago is coming to an end, and what better way to end a weekend getaway in Chicago than with drinks on a rooftop bar?

There are several rooftop bars scattered around the city.

Many of them are on hotel rooftops, but there are some independently owned rooftop bars in Chicago as well.

As you enjoy a beverage and look out at the Chicago skyline all lit up at night, you’ll be able to enjoy live music or play games like cornhole.

It just depends on what kind of atmosphere you prefer.

But one thing is for certain, it’s an excellent way to wrap up your trip to Chicago in a weekend!

Where To Stay For A Weekend In Chicago

Acme hotel company chicago.

One of the coolest hotels in Chicago is the Acme Hotel Company Chicago .

It’s a boutique hotel located in the heart of Chicago’s River North Neighborhood.

You’ll be just two blocks away from all the excellent shopping and restaurants on the Magnificent Mile.

Each of the rooms is uniquely decorated and many of them have views of the city.

They have a variety of room styles, including rooms with one queen-sized bed or one king-sized bed.

Their suites have two-queen-sized beds or a king-sized bed and come with views of the city and a larger floor plan.

The hotel also has a cocktail lounge, gym, and custom-brewed coffee room delivery services available.

Check Rates Here: Acme Hotel Company Chicago

Hotel Felix

Another great hotel in Chicago is the Hotel Felix .

The Hotel Felix is also in the River North neighborhood and is just a 14-minute walk from the beach.

It’s also just a quick walk away from Chicago’s Magnificent Mile.

The rooms are decorated in neutral tones, which makes it a very calming space to come back to after a day spent exploring the city.

They offer rooms with one queen-sized bed, one king-sized bed, or two queen-sized beds.

The hotel doesn’t have any dining options on-site, but it is very close to plenty of great restaurants in Chicago.

Check Rates Here: Hotel Felix

The Buckingham Hotel

You’ll find The Buckingham Hotel in the heart of Chicago’s Financial District.

In fact, it’s actually located on the 40th floor of the Chicago Stock Exchange building.

This luxurious hotel in Chicago includes access to an indoor pool, hot tub, and a fitness center within the Buckingham Athletic Club.

When you stay at The Buckingham Hotel, you’ll be just a 5-minute walk away from the Willis Tower and the luxury shops on State Street.

Plus, Grant Park and the Art Institute of Chicago are within a mile of the hotel.

They have a few different room options to choose from.

There are rooms with a king-sized bed or queen-sized bed that have views of the lake and deluxe double rooms, which have two full-sized beds.

They also have a beautiful one-bedroom suite with views of the city, a king-sized bed, a sitting area, and a small kitchenette.

Check Rates Here: The Buckingham Hotel

Where to Eat During Your 3 Days In Chicago

Enjoy breakfast at batter & berries in lincoln park.

One of the best places for breakfast in Chicago is Batter & Berries.

You’ll find Batter & Berries in Lincoln Park, which makes it a pretty convenient stop first thing in the morning.

The restaurant is probably best known for its ‘French Toast Flights’.

On the menu, you’ll find a wide variety of different French Toast concoctions for you to try.

Along with their French Toast, they also serve breakfast classics like breakfast sandwiches, omelets, and sausage biscuits and gravy.

Batter & Berries can get pretty busy, so if you plan on starting your day there, you might want to try and get there early.

Grab A Beer And A Meal At Revolution Brewing

Revolution Brewing is a really cool Chicago brewery and is actually the largest craft brewery in Illinois.

It’s independently owned and there are actually two locations in Chicago.

At the original location on Milwaukee Street, you’ll find the brewpub and restaurant.

You can stop by Wednesday through Monday for lunch and dinner.

On their menu, they have dishes like cheese curds, a large selection of burgers and sandwiches, and apple-wood smoked wings.

It’s very much a pub-style menu, but everything is delicious and perfectly pairs with the many brews they have on tap.

The Purple Pig Restaurant

One of the most highly rated restaurants in Chicago is The Purple Pig Restaurant.

With over 5,000 reviews on Google, where most of them are at least 4-stars, it’s clear this is a restaurant in Chicago you should visit.

The Purple Pig Restaurant is a fine dining experience located on Michigan Avenue.

Since opening in 2009, The Purple Pig Restaurant has been recognized for its excellence in some of the most prominent food publications. It’s even been Michelin recognized 8 years in a row.

The Purple Pig Restaurant is open daily for lunch and dinner, and reservations are highly suggested.

On their exquisite menu, you’ll find dishes like tuna tartare, salt-roasted beets, squid ink chittara, beef short ribs, and pan-seared Atlantic salmon.

The menu is pretty extensive and there is an entire section of just vegetarian dishes.

So there’s something for just about everyone to enjoy at The Purple Pig Restaurant.

Here are great tips on how to pack light on your next trip using only a carry-on!

There are so many great things to do and see during a weekend in Chicago! It makes for the perfect Midwest weekend getaway.

I hope you’ve found my Chicago tips helpful and now feel ready to plan your weekend getaway in Chicago.

Chicago is an amazing city that has something to interest everyone when you’re exploring Chicago in a weekend.

If you use this weekend guide to Chicago to plan your trip, I’d love to hear about your favorite parts in the comments!

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The Perfect 3-day Weekend in Chicago

Here's what to see, do, and eat on a long weekend trip to Chicago.

Meena Thiruvengadam is a lifelong traveler and veteran journalist who has visited more than 50 countries across six continents. Her writing has appeared in The Wall Street Journal , Departures , TripSavvy , and other publications.

If you’re looking for a quick escape, there's nowhere better than Chicago to spend a few days. It’s easy to get to Chicago from almost anywhere in the U.S., and there’s plenty more to do and eat than you'll have in terms of time — and appetite.

Here’s how to have the perfect three-day weekend in Chicago.

Valerie de Leon/Travel + Leisure

Kick off your long weekend in Chicago with a trip to Cloud Gate in Millennium Park. The sculpture, known colloquially as “The Bean,” is made of 168 pieces of stainless steel pieced together without any visible seams. The Bean is one of the most photographed spots in the city and has a 12-foot arch with an underside that warps and multiplies reflections.

Once you’ve got your perfect selfie, walk over to the Art Institute of Chicago to explore almost one million square feet of art, including Picasso's The Old Guitarist , Edward Hopper's Nighthawks, and Grant Wood's American Gothic . When you’re done, wander through Grant Park and check out Buckingham Fountain, as well as Chicago's public art scene .

Head across the river for an Italian Beef sandwich from Portillo’s for lunch. Then, hit the deck — the Skydeck Chicago at the Willis Tower that is. Formerly known as Sears Tower, this 110-story skyscraper held the title of the tallest building in the world for almost 25 years. Enjoying the view from its observation deck is arguably one of the best things to do in Chicago .

For dinner, grab a table at Quartino for a lively, family-style Italian meal. Don’t miss the eggplant parmesan, and do make a reservation ahead of time.

Start your Saturday in Hyde Park with brunch at Valois Restaurant, former President Barack Obama's favorite diner in the city (try one of his go-to dishes, the steak omelet with hashbrowns). Then, head to the University of Chicago campus to visit Robie House, designed by the famous architect Frank Lloyd Wright, who called the Chicago area home for the first 20 years of his career.

Afterward, ride the iconic “L” train north to pay Sue the Tyrannosaurus rex a visit at the Field Museum. As one of the largest natural history museums in the world, it's a dinosaur geek's paradise. While you’re there, walk over to Soldier Field, the picturesque home of the Chicago Bears, for a stadium tour . A VIP tour for $25 allows visitors to spend 15 minutes on the field.

Next, head to Giordano’s, Gino’s East, or Lou Malnati’s for a deep-dish pizza for dinner, then make your way uptown for a jazz show at The Green Mill. Al Capone was once a regular at the lounge, and his favorite booth is still standing. If the Green Mill looks familiar, it’s because you may have seen it in "High Fidelity," "Prelude to a Kiss," and "Soul Food."

Make a quick stop at the Doughnut Vault in River North for a sweet start to your Sunday. Doors open at 7:30 a.m. — you’ll want to get there early because the doughnuts never last long.

Afterward, head to the corner of Michigan Avenue and Wacker Drive for the Chicago Architecture Foundation’s river cruise . This 1.5-hour boat tour is well worth the $54 price tag and is one of the best ways to see Chicago and learn about the city's architectural history. The cruise passes by icons, including the Merchandise Mart, a building so big it once had its own zip code, and Marina City, a pair of residential towers known as "the corn cobs."

Stroll by the Chicago Theatre, then stop for lunch at Rick Bayless’ flagship Mexican restaurant, Frontera Grill. The restaurant won a James Beard Award in 2007 and has been a local favorite for decades.

Catch an afternoon comedy show at The Second City, which has hosted celebs including John Candy, Joan Rivers, Stephen Colbert, and Bill Murray. Then head to dinner in Andersonville, a Swedish enclave on the northern edge of the city that’s a rare oasis from national chains. Cap off your weekend in Chicago with a meal at Hopleaf, known for its mussels and fries, expansive craft beer selection, and CB&J — a cashew butter, raclette cheese, and fig jam sandwich.

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]

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3 Days in Chicago: The BEST Weekend Itinerary (By a Local!)

Planning 3 days in Chicago and seeking the perfect itinerary? I have lived in Chicago almost my entire life so I have created the perfect detailed Chicago 3 day itinerary with the best things to do, best places to eat, where you should stay, and all of my top tips, so that you can spend less time planning and more time enjoying the Windy City.

There is so much to do in Chicago but three days is enough to see most of Chicago’s top attractions . I have grouped each day by neighborhood so you don’t have to waste time getting around.

3 Days in Chicago Itinerary

3 Days in Chicago – Day 1

Lets start Day 1 in Chicago by enjoying some of the best views Chicago has to offer.

360 CHICAGO

For panoramic views of Chicago, head to 360 CHICAGO (formerly John Hancock Observatory), a public observatory on the 94th Floor of 875 N Michigan that offers breathtaking 360 degrees views of the city skyline and Lake Michigan.

The 360 Chicago observation deck is also home of TILT – Chicago’s highest thrill ride – an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th Floor.

Tip: 360 Chicago tends to be less busy and has shorter lines that the taller Willis Tower (on Day 2) but it is still best to visit in the morning to avoid crowds. (Click here to buy a skip the line ticket ).

Shop (or Window Shop) on the Magnificent Mile

After visiting 360 Chicago, walk south on Michigan Avenue and join the throngs of visitors and locals shopping (or window shopping) on The Magnificent Mile. The Magnificent Mile (or The Mag Mile), is an upscale section of Michigan Avenue, running from Oak Street to the Chicago River. Although some of the stores on Michigan Avenue are pricey, it is totally free to window shop. Landmarks on the Mag Mile include the historic Chicago Water Tower, the Tribune Tower and the Wrigley Building skyscraper.

Take an Architecture River Cruise

Chicago has amazing architecture and the best way enjoy it is by taking an architecture river cruise . Because the water sometimes freezes, river cruises don’t usually run in the winter.

If you are visiting Chicago in the summer, you can do a longer combined architecture river and lake cruise to see the skyline from the lake as well.

An alternative to a river cruise is to take a walk along the Chicago Riverwalk . The Riverwalk is one of the best spots in Chicago for people watching and there are also restaurants , shops and places to sit along the way. You can see a map of attractions on the Riverwalk here .

Go on a Gangsters Tour

Chicago has a long  history of organized crime and is famous for being the home of mafia figure Al Capone. There are many mob tours for those that want to learn more about the history of organized crime.

Food or Drinks with a View

Chicago has several rooftop bars and restaurants with amazing views of Chicago.

Cindy’s (12 S Michigan Ave) is a restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located across Millennium Park which offers panoramic instagram worthy views of Millennium Park and Lake Michigan. This is a popular spot and the wait for the elevator can be long but if you visit around the time it opens (10 am on the weekends and 11 am on some weekdays) you can enjoy the great views without the crowds.

LH ON 22 (85 East Wacker Drive) -Enjoy classic cocktails and small bites from the outdoor LH terrace of LondonHouse Chicago which offers great views of the Chicago River, Lake Michigan and the Magnificent Mile.

The J. Parker (1816 N Clark St) is a stylish bar and restaurant on the rooftop of the Hotel Lincoln with great views of Lincoln Park.

3 Days in Chicago – Day 2

From the highest vantage point of the city to the famous Bean, Day 2 in Chicago will take you to Chicago’s best and most famous attractions.

Skydeck at Willis Tower

The Skydeck at Willis Tower (formerly known as the Sears Tower and what locals still call it) is the most well known of Chicago’s two tall skyscrapers with public observatories. The Willis Tower is the tallest building in the Western Hemisphere and was the tallest building in the world from 1974 until 1998.

If you are not scared of heights, you can stand on the Ledge’s glass boxes that extend out over 4 feet from the Skydeck.

Tip:   Lines for the Skydeck can get very long (especially on weekends) so avoid the crowds it is best to visit first thing in the morning as soon as it opens or in the evening. (Click here to buy a skip the line ticket ).

See The Bean at Millennium Park

If you have seen photos of Chicago on social media, chances are you have seen photos of Cloud Gate (also called The Bean), the famous mirrored sculpture in Millennium Park.

Please note that due to construction, public access and views of Cloud Gate are limited through spring of 2024.

Although The Bean is very touristy, don’t skip it. It is one of the most instagrammable places in Chicago and it is a great spot to take photos to remember your trip to Chicago.  The Bean is usually crowded especially in the summer and on weekends so if you don’t want other people in your photos visit early in the morning.

The free Millennium Park is part of Grant Park and also includes the Jay Pritzker Pavilion, the Crown Fountain sculpture and Lurie Garden. In the winter, there is a free ice skating rink right in front of the park. On hot summer days, kids (and some adults) love to splash in the water from the Crown Fountain .

If you are visiting Chicago with toddlers and young kids, you might want to also visit Maggie Daley Park , a large public park connected to Millennium Park that has play areas for kids of various ages, a fieldhouse, climbing wall and another ice-skating ribbon in the winter.

Art Institute of Chicago

Chicago has many great museums which are worth visiting but my top pick is the  Art Institute of Chicago conveniently located next to Millennium Park. It is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. (Click here to buy a skip the line ticket if you want to avoid long lines).

Some locals consider Navy Pier a bit of a tourist trap, but it is a not to missed attraction especially for those visiting Chicago with kids. Navy Pier is full of fun things to do including a large Ferris wheel, rides and games, the Chicago Children’s Museum and several shops, restaurants (including Giordano’s and Garrett Popcorn Shops) and bars. Navy Pier is also the starting point for various sightseeing cruises and boat rides.

Tip: If you are visiting Chicago in the summer, stay or come back for the free fireworks at Navy Pier every Wednesday at 9 pm and Saturday night at 10 pm. You can even watch the show from the water on a sightseeing cruise .

3 Days in Chicago – Day 3

Here are my suggestions for your third and final day sightseeing in Chicago. If you are visiting Chicago on a Sunday morning, head to Maxwell Street Market , one of the best places for Mexican food.

Visit One or More Museums

Chicago has many great museums which are worth visiting. The Field Museum , the  Shedd Aquarium and Adler Planetarium are all located close to each other on The Museum Campus. The Adler Planetarium Skyline Walk has one of the best skyline views of Chicago .

The Museum of Science and Industry is located in Hyde Park and is a bit out of the way from downtown Chicago but it is a really fun museum with hands-on activities and interactive exhibits. If the weather allows and you have extra time in Hyde Park, you might want to check neighboring Jackson Park . This park has cherry blossom trees in the spring and it also has a free Japanese garden.  Promontory Point is about a half mile away and has great skyline views of Chicago.

Tip:   If you are visiting a few museums and indoor attractions, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.

Explore the Lakefront Trail and Beaches

Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan and it is a great spot to people watch and get some exercise.  In the summer and weekends, the lakefront is packed with locals and visitors walking, running and riding bikes.  You can find a map with the access points here .

Most people don’t think of Chicago as a beach destination but Chicago has many beaches on Lake Michigan.   Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions. North Avenue Beach is more of a party beach and is located close to Lincoln Park.

More Things to Do in Chicago

If you have more time or not a fan of museums or tall buildings, here are some more fun things to do in Chicago:

Find Street Art

Chicago is full of street art and there are always new murals popping up.  One of the most famous Chicago murals is “Moose Bubblegum Bubble” (pictured above) by Jacob Watts which located at 33 E. Ida B. Wells Drive (formerly 33 E. Congress Parkway). It is part of the Wabash Arts Corridor which is walking distance to Millennium Park, The Art Institute of Chicago and other well known tourist attractions. You can find more detailed mural walks in the Loop here .

Another famous mural is The Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and other street art on this street art tour .

Another neighborhood that has a high concentration of street art (as well as great Mexican food) is Pilsen.

Watch a Cubs Game at Wrigley Field (or attend another sporting event)

Chicago is known for their love of their sports teams, so if you are visiting during the season you might want to attend a sporting event. To those unfamiliar, historic Wrigley Field is home to one of the city’s baseball teams – the Cubs.  Whether a fan of the Cubs, baseball in general or just a fun atmosphere, a day at the 100 year old ballpark is a must for locals and tourists alike.  You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere while drinking and eating. (There are also tours of the stadium offered during the off season).

Enjoy One of Chicago’s Many Festivals

Chicago always has at least one or more festivals or events happening every weekend especially in the summer .  Some Chicago festivals are very well known and attract thousands of tourists, but there are many festivals and events in Chicago where you will mostly find locals. For great food, music and people watching, check to see if there are any festivals or events  going on while you are in town.

Walk The 606

The 606 is Chicago’s version of The Highline in NYC , an elevated trail goes through 2.7 miles of the city’s northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square.  It is a bit off the beaten tourist path but it great place to walk, run or bike.  There are several access points so you can get off the trail to explore the various neighborhoods.

Where to Eat in Chicago

Chicago is known for its food so get ready to eat! Chicago is one of the best cities in the world for food and I could easily write a whole post just about the food! Although Chicago is famous for food like deep dish pizza and Chicago-style hot dogs – there is so much more great food in Chicago.  Don’t limit yourself to just deep dish pizza and hot dogs, but you should try those if you are visiting Chicago for the first time.

Lou Malnati’s and Giordano’s  are two of the best restaurants for deep dish pizza. Giordano’s can be found in several spots throughout the city including Navy Pier, near Michigan Avenue and near Millennium Park.

Many locals consider Pequods in Lincoln Park to have the best deep dish pizza in Chicago. Their version has a caramelized crust.

For Chicago style hot dogs (remember, no ketchup allowed) try Portillos , a popular chain.

Al’s Italian Beef (169 W Ontario St.) is famous for its Italian beef sandwiches.

For original Chicago-style popcorn head to Garrett Popcorn Shops, with a location near Millennium Park and Navy Pier.

To get an overview of the food scene consider a food tour:

Where to Stay in Chicago

Most people visiting Chicago stay in the downtown area including the Loop, River North, Gold Coast, Streeterville and Michigan Avenue since they are close to most of the major tourist attractions. If you are visiting during the weekend, the Loop is a great option as it is more quiet at night. River North (where I live) is close to nightlife and restaurants, but noise can be a problem especially during the weekends. Here are some of my top picks for the best hotels in Chicago :

The Peninsula Chicago.   If you are looking for a luxury hotel, The Peninsula Chicago is one of the best hotels in Chicago with a world renown spa and a half-Olympic length swimming pool overlooking the Chicago skyline. It has a central and convenient location right off the Magnificent Mile, close to shopping and less than a block from the Water Tower and 360 Chicago. Click here to see the latest prices and click here to read reviews .

Hilton Chicago/Magnificent Mile Suites.  Recently renovated all-suite hotel with fridge and microwave in room. Great location just steps from Michigan Avenue and one block from Lake Michigan.   Click here to see the latest prices and click here to read reviews .

ACME Hotel Company. This modern, stylish and unique hotel is located in downtown Chicago 2 ½ blocks from the Magnificent Mile in River North. Offers great value and great service. Click here to see the latest prices and click here to read reviews .

Best Western River North Hotel. Convenient located in the heart of River North close to the Chicago River as well as many restaurants and bars. Amenities include free high-speed Wi-Fi, deeply discounted parking, room service, fitness center, indoor pool and sun deck.  Click here to see the latest prices and click here to read reviews .

The Best Time to Visit Chicago

Chicago has plenty of things to do year round whatever the season. Summer is one of the best (and busiest) times to visit Chicago as the city comes alive and there are always outdoor festivals, concerts and events going on where you can take advantage of the warm weather. Restaurants and bars open their rooftops and sidewalk patios so you can dine outside. The temperature in the summer is usually hot but not unbearable (but some days can be very hot and muggy).

Winter can be very cold and snowy but some years can have mild winters with hardly any snow. Late November and December are busy with holiday events and festivities and the temperatures are usually still not that cold.  January and February tend to be the coldest months but attractions are less crowded. Even if you hate cold weather, there are enough indoor attractions to keep you entertained in Chicago during the winter .

Fall and spring are generally great times to visit Chicago – the popular attractions are not as busy as summer and the weather is usually more pleasant (but temperatures can be very unpredicable). The weekend before St. Patrick’s Day and the weeks during spring break can get very busy but the rest of spring is considered shoulder season.

Personally, I think the best time to visit Chicago is September and early October because students are back in school but temperatures are still warm but not as hot and humid as summer.

If you still need help deciding when to visit Chicago, check out The Best Time to Visit Chicago – A Month By Month Guide  for more details regarding weather and events by month.

Getting Around in Chicago

Chicago is an easy city to get around in with many public transportation options. Both Chicago airports – Chicago O’Hare (ORD) and Chicago Midway (MDW) – are connected to downtown Chicago by train.

For longer distances you can use public transportation , taxi, rideshare or rent bikes through Divvy (Chicago’s bike share program).

Taxis are plentiful and very easy to find downtown and at popular tourist attractions. You can also use the Curb app (for taxis) or ridesharing apps ( Lyft and Uber) to get around Chicago .

A hop on hop off bus is a great way to see all the attractions without having to figure out how to get around.

These are my top choices for the best things to do if you have 3 days in Chicago .

Planning a trip to Chicago? Check out more of my Chicago guides and itineraries:

• Best Things to Do in Chicago in the Summer
• 24 Hours in Chicago: A Perfect One Day Itinerary (From a Local)
• Most Instagrammable Places in Chicago
• Best Free Things to Do in Chicago
• Best Day Trips From Chicago

Related Posts

savvyglobetrotter

One comment.

Hi, I have also lived in Chicago and yes, although Summer is great, the best time to visit I’d also say it’s Aug/Sept. This is one, if not THE one, of the best places on Earth. I’d even say, if you can stay longer than 3 days in Chicago, do so. You are not going to regret it, since the city offers so much to do year round. Lovely post!

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Chicago style Weekend

Planning a weekend in Chicago? From film buffs to sports fans, there’s a Chicago style weekend for everyone. Here’s how to spend a jam-packed 48 hours in the city.

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• 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.

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Home » North America » Chicago

Weekend in CHICAGO – INSIDER GUIDE (2024)

Chicago is one of the largest cities in the United States. Located on Lake Michigan in Illinois, the “Windy City” is famous for its bold architecture, world-renowned museums, and classic American cuisine. A weekend in Chicago will keep you busy, active & well fed!.

Chicago is home to some of the most iconic, and tallest buildings in the world! In fact, Chicago is actually the birthplace of the modern skyscraper which makes it an absolute must-visit city for any budding architects!

The city is also filled with some of the country’s best museums ranging from amazing art museums to fully interactive science museums.

This city on the shore is a great place to visit and definitely worth exploring on your next weekend break! Here are our top recommendations of the best things to do in Chicago this weekend!

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Insider Tips for an AMAZING Weekend in Chicago

Chicago nightlife guide, chicago food guide, sporting events in chicago, weekend cultural entertainment in chicago – music/concerts/theatre, chicago weekend travel faqs.

A weekend trip to Chicago is a great amount of time to explore the city, and you can easily get   to see a lot. Check out our top tips to get the most out of your stay in the Windy City!

With a Chicago City Pass , you can experience the best of Chicago at the CHEAPEST prices. Discounts, attractions, tickets, and even public transport are all standards in any good city pass – be sure invest now and save them $$$ when you arrive!

Know Where to Stay in Chicago

When choosing a place to stay in Chicago , do be mindful of its location as well as its amenities. To get around the city conveniently and to be nearby some iconic Chicago attractions, we recommend downtown or in a central location.

Downtown Chicago (known locally as The Loop) is one of the best places to stay in Chicago, for first-time visitors! It’s utterly central, houses Chicago’s most popular landmarks and is well connected by the city’s public transportation system; it’s the perfect base for spending 2 days in Chicago!

The Windy City is huge so and it can be a bit overwhelming trying to choose your accommodation. In case you are in a hurry though, here are three of the best accommodation options we recommend for a great weekend stay in Chicago!

Our Favorite Hostel – HI Chicago

• Ideally located right in the city center
• There are options for gender-separated dorms with en-suite bathrooms

This hostel is close to all of the city’s top tourist attractions, including art galleries, museums, shops and restaurants. It has over 500 comfortable beds, and offers free breakfast and walking tours throughout Chicago.

Our Favorite Airbnb – Artsy Apartment with Funky Vibes

• With some wicked deco choices!

With this basic, convenient and well-priced studio apartment, you have access to a comfortable, queen size bed, full kitchen, on-site laundry facility, free wifi, and an awesome host who will recommend you places to visit, attractions to see in Chicago.

Our Favorite Budget Hotel – Freehand Chicago

• Located in the heart of Chicago!
• Just a short walk from the Magnificent Mile!

Housed in a classic 1920’s building, Freehand Chicago is a charming and stylish hotel. The decor has an industrial modern theme. In addition to the usual hotel amenities there is also a cocktail bar, gym and laundry facilities.

• AMAZING Airbnbs in Chicago
• Chicago’s Best Hostels and Budget Accommodation

Know How to Get Around in Chicago

Walking is a great way to explore Chicago and a lot of the best places to see are conveniently located in the central downtown area. Most Airbnbs in Chicago are also located centrally.

However,  Chicago is a big city that’s spread out over a large area so walking between the various neighbourhoods can be very time-consuming. 

For moving between Chicago’s neighbourhoods, there is a vast network of public transport options. The L Train has stations all over Chicago and is a great way to explore the city! There is also an army of efficient buses that connect the train stops to most Chicago points of interest. 

If you don’t fancy spending time on the public transport system, then bicycles are a great option! There are a few bike rentals in Chicago as well as the city’s bike-sharing system known as “Divvy Bikes” with bases around the metro stations 

The Divvy bikes are an easy and affordable way to get around, especially over a weekend in Chicago. Plus, it’s probably one of the most fun you can have while visiting Chicago !

Most hotels in Downtown Chicago have some sort of bar attached, which makes for an easy choice for a quick drink. If you want to experience the authentic atmosphere of Chicago’s nightlife, it’s best to venture out into the suburbs. Here are three great options for a good night out!

River North

• Close to Downtown and well connected by public transportation
• The most popular bars in the area are El Hefe, Howl at the Moon and Mother Hubbard’s 
• Be sure to hit up Hubbard Street to experience an authentic Chicago Saturday night!

Head down to Hubbard Street in River North for a wild night out! Whether it’s a weeknight, or the weekend, the bars in this area are a hive of activity! This is Chicago’s top nightlife district, and it attracts just about everyone! It’s also the best area in the city to go bar hopping with friends!

Wrigleyville

• For a unique Chicago experience head to Clark Street and catch a Cubs game 
• Cubs fans fill up most bars, and it can get rowdy!
• Irish Oak, Deuces and the Diamond Club and Sluggers are three great options! 

Head to Clark Street in Wrigleyville and experience the nightlife with the locals! This long street is full of bars and watering holes; it may even be the longest cluster of bars in the city! The energy is especially high during Cubs games and Saturday nights. This area attracts a slightly younger crowd, and the bars can get festive!

Wicker Park

• Head to North Milwaukee Avenue and you’ll find an eclectic mix of bars, pubs and clubs 
• Some of the more popular spots include Whiskey Business, SWIG and Debonair
• Around Logan Square, just a few blocks up Milwaukee, is another small cluster of bars with good vibes 

Wicker Park provides a more alt scene for people looking for more unusual things to do in Chicago . The main artery is North Milwaukee Avenue. You’ll find a funky mix of pubs, clubs and bars that attracts a colorful bunch of party-goers! While this area is well serviced with public transport, it may be a good idea to catch a taxi when returning home.

If you’re a fan of pizza, then you must try the famous Chicago-style deep dish pizza which is now a hit across the US! The Chicago-style hot dog is another dish Chicagoans take great pride in. 

Here are some stellar recommendations for where to eat in Chicago.

Lou Malnati’s Pizzeria

• You can find this popular pizza chain in almost every neighborhood of Chicago!
• Order online and have your food delivered, or sit down and eat in the restaurant
• Don’t leave Chicago without trying some of their world-famous pizza!

Widely regarded by locals as the best place to get a deep-dish pizza, Lou Malnati’s is one of Chicago’s best-known pizza chains! It is, therefore, no surprise to learn that it was founded by the son of Rudy Malnati, the guy who helped developed the recipe for Chicago-style pizza!

Gene & Jude’s

• Well-known for serving the best Chicago-style hot dogs in the city! 
• This popular food stand is packed with customers all day long
• Each hot dog is served with fries, whether you like it or not!

Another icon of the city is the Chicago hot-dog, and it’s no secret that Gene & Jude’s make them best! The true Chicago dog comprises a Vienna sausage in a poppy seed bun with mustard, relish, chopped onions, hot peppers, tomatoes, dill pickles and a dash of celery salt. You won’t find ketchup anywhere on-site!

Take a Food Tour in the City

• Enjoy deep-dish pizza, the original brownie, a Chicago-style hot-dog and local craft beer!
• See some of Chicago’s most famous spots, including Millennium Park, Palmer House Hotel, the Art Institute and the Bean
• 2.5-hour food themed walking tour through the streets of Chicago

For a comprehensive understanding of the city’s cuisine, take a food walking tour and taste all the iconic dishes that have come out of Chicago! This tour combines an enjoyable walk around Chicago’s Downtown area with plenty of stops to sample some of the city’s famous tastes!

Sport is definitely one of the Chicago highlights and you can get out and be active no matter the season! Whether you prefer taking part in an activity, or just watching, there are always plenty of options on offer!

Wrigley Field

• First opened in 1914, this is one of America’s most iconic baseball parks 
• Home of Major League Baseball team the Chicago Cubs
• Known for its ivy covered home-run wall, it’s the second oldest stadium in MLB!

If your weekend getaway to Chicago coincides with a baseball game, do your best to rustle  up some tickets and soak in the festive atmosphere of America’s favorite pass time! Wrigley Field baseball stadium is located on the north side of Chicago and is easily accessible by public transportation.

Chicagoland Speedway

• Head to Chicagoland Speedway to test your high-speed driving skills and get your adrenaline going! 
• Choose between a range of heart-pumping driving experiences
• Set your fastest lap on a real NASCAR speedway!

If your racing addiction demands more than just a seat on the sidelines, check out Chicagoland Speedway ! This fun location offer exciting options that will definitely satisfy your need for speed! Get behind the wheel of a NASCAR and take it for a spin on Chicago’s NASCAR speedway!

Fame Play Ping Pong at Acebounce

• Challenge your friends to a game, or three of ping-pong
• Work up a thirst, then enjoy some drinks from the on-site bar
• A great social source of fun on a weekend trip to Chicago!

If you’re looking for an indoors activity in Chicago, look no further than Acebounce where you can enjoy games of ping-pong, or beer pong! Sink a few pints and dance to the beat from live DJ’s! This is a fun way to spend a chilled-out Sunday in Chicago. 

Wanna know how to pack like a pro? Well for a start you need the right gear….

These are packing cubes for the globetrotters and compression sacks for the  real adventurers – these babies are a traveller’s best kept secret. They organise yo’ packing and minimise volume too so you can pack MORE.

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Your Chicago itinerary should include some nocturnal fun and the city has plenty of great music and theatre options. Here are three of Chicago’s best venues for entertainment!

Green Mill Jazz Club

• A great venue to listen to jazz all night long 
• Arrive early, grab a cocktail and settle in for a relaxing evening of free jazz and bebop!
• This was a local hangout for Al Capone and other gangsters during the 1920s

Green Mill Jazz Club in Uptown Chicago is a former speak-easy dating back to 1907. It’s the longest continuously running jazz club in the country! Slip into one of the glamorous curved booths and listen sultry singers, big band and bebop! This is one of the most entertaining things going on in Chicago this weekend! 

The Hideout

• A great place to go for live music on a Saturday in Chicago 
• An intimate prohibition-era bar that host all sorts of live music and dancing 
• Check out their line-up on their calendar page

This beloved Chicago hangout has a bar in the front and a stage in the back. It offers a cozy vibe and casual aesthetic. After you find the obscure industrial side-street it’s hidden on, you’ll join a welcoming crowd. The outside patio is also used for eclectic music sets, weekly bingo, and comedy and dance nights! 

Andy’s Jazz Club & Restaurant

• Enjoy live jazz music 7-nights a week at this superb venue!
• A lively atmosphere that lends itself well to enjoying live music
• Food is also available at their restaurant 

This mainstream jazz club runs regular, low-key residencies with some of Chicago’s most respected jazz musicians! There are regular performances that showcase the local jazz talent. This venue is a comfortable, intimate space where you can drop by for a cocktail and a bite to eat. Andy’s is sure to draw a crowd any day of the week, especially in Chicago on Sundays! 

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8 Other Awesome Things to do in Chicago This Weekend

So, you’re still looking for more fun stuff for your trip to Chicago ? Need more Chicago weekend events and attractions? Not to worry, we’ve got you covered!

Here are 8 more activities, attractions and events in Chicago this weekend! 

#1 – Stop in at the Field Museum

The Field Museum is Chicago’s premier natural history museum and one of the largest of its kind in the world!

Founded with an endowment from Marshall Field, it has since gone on to house one of the finest collections of artefacts in the United States. Everything from precious gems to a Tyrannosaurus-Rex skeleton are found here.

Permanent exhibits range from animal dioramas to interactive displays that engage all ages. There are also cultural displays, walk-throughs detailing the planet’s evolutionary processes, and exhibits delving into cellular-level research and technology!

#2 – Stand Above the City Skyline at Chicago Sky-deck

SkyDeck Chicago is located at the very top of the Willis Tower, which is one of the tallest buildings in the world! After a short ride to the top, you’ll be amazed by the sheer height of the viewing deck, and just how far you can see beyond the city! 

There are windows on all sides of the observatory that offer unparalleled panoramic views of the surrounding city, and beyond! There’s also an all-glass enclosure that looks straight down onto the busy streets of Chicago! Enjoy a movie detailing the 45-year history of the Willis Tower and Chicago’s other architectural wonders.

#3 – Go Shopping Along the Magnificent Mile

The Magnificent Mile is a row of exclusive shops, department stores and boutiques that line the northern half of Michigan Avenue. If you’re spending 3 days in Chicago, make sure to visit one of the best shopping districts in town!

Originally designed by 19th-century architect Daniel Burnham, this famous section of Michigan Avenue has a plush assortment of historic buildings in various architectural styles. Among its jewels are the Tribune Tower, the Wrigley Building, the John Hancock Center, the Drake Hotel, and the Historic Water Tower; one of the few structures that survived the Great Fire of Chicago.

This hostel is close to all of the city’s top tourist attractions, including art galleries, museums, shops and restaurants.

• Free Breakfast
• 24 Hour Reception

#4 – Admire the Grand Works of the Art Institute of Chicago

The Art Institute of Chicago is located in the center of Grant Park along Michigan Avenue. It’s the country’s second largest art museum and everything about this art institute is impressive! Most notable are the two famous lion statues that were sculpted by Edward Kennys for the museum’s opening in 1893.

The museum has an incredible collection of French Impressionist paintings and other artworks from around the world! A visit to this museum is a must for art-lovers, who will especially enjoy this addition to their Chicago itinerary. 

Some of the most famous pieces include Chagall’s America Windows , Matisse’s Bathers by the River , and Georgia O’Keeffe’s Black Cross, New Mexico.

#5 – Visit Navy Pier

Navy Pier extends out into Lake Michigan at the mouth of the Chicago River. It boasts a newly-redesigned Ferris Wheel, called the Centennial Wheel, as well as a handful of other amusement park rides. 

The pier is also home to the Children’s Museum, Chicago Shakespeare Theater, weekly fireworks, numerous eating options, and live concerts! Stroll around the pier to enjoy everything it has to offer, or take a Chicago river cruise on one of the many boat tour companies that moor at the pier during the warmer months.

#6 – Take an Architectural River Cruise

A Chicago architecture river cruise is a great way to view Chicago’s hidden gems and iconic landmarks from the water! Architecture and building design play a big role in Chicago’s culture. Many of the world’s most famous architects have hailed from Chicago, and some of the most famous buildings are part of its skyline. 

Take a cruise and admire some of the most famous and unique buildings along the river. Learn about the history and creation of over 50 Chicago skyscrapers. This cruise is one of the coolest things to do this weekend in Chicago!

If you’re looking for a more memorable way to see the river and Lake Michigan, you might consider renting a boat in Chicago , which will take you and your party anywhere you want to go!

#7 – Visit the Museum of Science and Industry

The Museum of Science and Industry is located in Hyde Park which is a little bit further out from the city center, but absolutely worth the trip! This museum was part of the Columbian Exposition of 1893.

The institution’s collection includes many unique artefacts and displays, including Colleen Moore’s Fairy Tale Dollhouse , made from precious gems and materials. Also on display is a WWII German submarine and a Pioneer locomotive. Definitely go check it out if you have extra time on your weekend trip to Chicago!

#8 – Snap a Photo at the Cloud Gate Sculpture at Millennium Park

Don’t miss a chance to visit Cloud Gate, the famous sculpture by Anish Kapoor. This attraction is located in Millennium Park, at the north end of Grant Park. Also known as “The Bean”, its curved, mirrored finish creates fascinating reflections and captivates everyone that passes by!

This famous Chicago landmark is an absolute must-see when visiting! This park is also home to a two glass tower fountain. The tower fountains have faces projected onto them to make them look as if their mouths are streaming water into the pool!

Even a weekend trip requires some research to get the most out of your visit. To keep that research time to a minimum for you, we’ve compiled some of the most frequently asked questions about a weekend trip to Chicago! 

What should I pack for a weekend in Chicago?

In addition to the essentials, here are a few things we recommend you pack before embarking on your Chicago weekend. – As many of Chicago’s points of interest are concentrated in a few suburbs, it’s often best to walk between them. Therefore make sure to pack some comfortable  walking shoes  with support! Don’t forget to also pack some  formal shoes  if you plan on hitting up a jazz lounge or two! – Chicago’s weather can get pretty extreme ranging from howling blizzards in winter to steamingly humid days in summer! Make sure you pack some  layered clothing , and be prepared to expect the unexpected any time of the year! Even in summer, the nighttime temperatures can get a bit chilly.  – Pack a  reusable water bottle  to keep hydrated if you plan on walking around a lot. There are many water fountains in the city where you can fill up, so there is little need to buy bottled water. Not only will you be saving money, you’ll also be doing your part to save the environment!

Can I get an apartment in Chicago for the weekend?

Most definitely! Airbnb is the perfect option for booking your accommodation in Chicago. You can easily filter whatever amenities you prefer (kitchen, parking on-site, TV, etc) and enjoy all the luxuries of having your own place for the weekend! This is a great money-saving option for larger groups, as you can find larger accommodation and split the cost without having to pay for separate hotel rooms!  Staying in an Airbnb also comes with the added bonus of being able to stay with a local. There are plenty of friendly hosts who are willing to provide visitors with insider tips and useful insight on how to make the most of a two-day stay in Chicago!  Booking.com  also has apartment listings on their website to choose from, and often in premier locations. A perk to this is that you go through a company for booking accommodation, and not a private individual. 

Is Chicago safe for a weekend trip?

Chicago is largely a safe city , and tourists shouldn’t have too much to be worried about when walking around downtown or when visiting well-known landmarks. However, it is always a good idea to do some research or ask locals before venturing out to the peripheral neighborhoods of the city. Chicago does experience violence and crime, but this is predominantly confined to specific hotspots, such as the far West Side of Chicago and the South Side of Chicago. While these areas are clearly dodgy, and gang violence and crime does occur, they are well away from Downtown Chicago.  Be aware of your possessions when in crowds or around busy areas as pickpockets do frequent popular sights in the city. At night, it is best to keep to well-lit streets and populated areas as muggings do occur in dark side streets after dark. Be sure to check the weather forecast for potential natural hazards, which can occur during the particularly harsh Chicago Winter.

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ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

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Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

Final Thoughts on a Great Weekend in Chicago

Now that you have the best information on what to do in Chicago this weekend, all that’s left to do is pick the weekend that suits you and enjoy an incredible Chicago trip!

This city has a rich history, vibrant music scene, impressive architecture, and delicious food! There’s an array of impressive sights dotted throughout the city, and although it’s a large city, getting around without a car should be pretty easy!

Be sure to take in all the quirkiness and nuances that the Windy City has to offer! It’s possible to see a lot of Chicago in 3 days if you plan correctly.

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

Aiden Freeborn

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• 1 Door County, Wisconsin
• 2 Indianapolis, Indiana
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• 4 Grand Rapids, Michigan
• 5 St. Louis, Missouri
• 6 Lake Geneva, Wisconsin
• 7 Milwaukee, Wisconsin
• 8 Galena, Illinois

8 Best Chicago Weekend Getaways

With slick boutiques, a handful of the country’s hottest kitchens, and more than a few rapidly-evolving neighborhoods, Chicago to-do lists are easier to add to than cross off. But given it’s within driving distance of so many other Midwestern gems, Windy City residents should step outside Chi-Town limits every once in awhile. Here, 8 easy weekend getaways, from midsize cities like St. Louis, Missouri, to quaint, unincorporated villages like Saugatuck, Michigan.

A Brooklyn-based writer and editor, Chelsea's work has appeared in Matador Network, The Huffington Post, the TripAdvisor blog, and more. When not planning her next trip, you'll usually find her drinking way too much iced coffee (always iced—she’s from New England) or bingeing a Netflix original series.

See recent posts by Chelsea Stuart

Door County, Wisconsin

3 hours and 45 minutes by car from Chicago

With nearly 300 miles of Lake Michigan and Green Bay coastline, it only makes sense that Wisconsin's Door County picked up the nickname “The Cape Cod of the Midwest." Along with sandy sheltered beaches and rugged limestone cliffs, the peninsula is known to harbor extensive cherry orchards, hyper-local farm-to-table restaurants, and five state parks. If you only have time for one of the latter, don’t miss Whitefish Dunes, with its mile-long shore, towering dunes, and 14 miles of trails which crisscross the eastern end of the county. Of course, Wisconsin’s great outdoors can also be admired in a different, more adult way: on the Door County Wine Trail . Start your crawl in southern Algoma, and work your way through the region’s eight fruit-wine-producing vineyards ending in Fish Creek. Before the cherry and apple varieties get the best of you, head just a little further north to Wickman House in Ellison Bay. Situated in a village of just 165 people—and supplying its kitchen with produce from an onsite garden, the historic restaurant is as quaint as they come, but don’t let its looks fool you—the innovative menu (think: kimchi-stuffed grilled trout) is refreshingly big city.

Indianapolis, Indiana

3 hours by car from Chicago

Indianapolis may have more than a million less residents than Chicago, but make no mistake, the gentle-mannered Midwestern city is still “big” in its own way. Even beyond its sport mecca status, the Indiana capital has a lot under the hood, including a thriving culinary scene and renowned cultural institutions left and right. Of course, first-time visitors have to hit the Canal Walk—a three-mile loop that runs along Indy’s downtown waterfront. But once you’ve squeezed that in, make a meal-time detour to The Vanguard . With tempting large plates like half a fried chicken with honey slaw, peach butter, hot sauce, pickles, and a biscuit, the Broad Ripple restaurant weaves sometimes subtle, sometimes obvious southern flavors throughout its New American dishes. Before your weekend comes to end, drop by the IMA—aka the Indianapolis Museum of Art —for a lesson in African, American, Asian, and European art. The encyclopedic museum is filled with more than 54,000 pieces; with works from Neo-Impressionist paintings to 19th-century Irish embroidery, everyone’s bound to find something that interests them.

Saugatuck, Michigan

2.5 hours by car from Chicago

If you’re like us, the cornerstone of any great day is killer cup of coffee. In Saugatuck—a tiny beach town of roughly 1,000 on Lake Michigan’s eastern shore—Saturday’s are best started with cold brew or Costa Rican drip from Uncommon Coffee Roasters . Caffeine safely secured, make for Oval Beach , a pristine public stretch just minutes from another one of the town’s main attractions: Mount Baldhead Park . Visitors who pant their way 300+ steps up to the top of Mt. Baldhead are rewarded with panoramic views of Saugatuck and Douglas just to the south. Once you’re properly tuckered out, unwind at the Wickwood Inn . With an owner that doubles as a cookbook author, the romantic B&B prides itself on fresh (and free!) farm-to-table breakfasts, evening hors d'oeuvres, and sweet treats. Pair stellar onsite dining with French country decor, plush featherbeds, and roaring open fires, and you may just find yourself calling in sick on Monday to extend your trip a day or so.

RELATED : 9 Best Hotels in Chicago

Top Images courtesy of Frederik Meijer Gardens & Sculpture Park

Grand Rapids, Michigan

When it comes to Chicago weekend getaways, Michigan’s second-largest city is an easy choice. Just a 3-hour drive north (along Lake Michigan’s shore), Grand Rapids rolls out the welcome mat with a surprising number of acclaimed art and history institutions, and more than 60 craft breweries (which lend it its “Beer City” moniker). While you’re in town, you’ll want to grab a bite at one of Downtown Market’s 21 vendors (think: Neapolitan-inspired pizzas and slow BBQ) and follow it up with a drink at Brewery Vivant . Go for a Plein de Vie pour like the Harvest Breed or Stone Fruit Sour to get a taste of something traditional; undergoing wild fermentation, the series pays homage to early Belgian brewing processes. Once you’ve satisfied your epicurious side, take a drive to the outskirts of town to spend an afternoon at Frederik Meijer Gardens & Sculpture Park . With 158-acres of indoor and outdoor sculptures (including a piece from Dale Chihuly), highly-curated gardens, and exhibits of works from illustrious French artists like Auguste Rodin and Edgar Degas, it’s easy to lose track of time.

St. Louis, Missouri

4.5 hours by car from Chicago

St. Louis may play second fiddle to nearby hubs like Chicago and Philly, but the second-tier city is worthy of at least one of your weekends. Last spring, Vicia —a veggie-centric spot with casual counter-service lunches, a la carte dinners, and 15-course tasting menus—made waves when it opened with STL native and former Blue Hill at Stone Barns chef de cuisine Michael Gallina at the helm. Drop by the lauded kitchen—it’s topped many best 2017 openings lists—for wood-fired family dishes like milk brined cauliflower with romesco sauce and curried almonds, and Berkshire pork with grilled apple puree. Once you’ve overstuffed yourself, skip the Arch and head for a walk at Laumeier Sculpture Park in Sunset Hills. The free and open to the public park was one of the country’s first and largest, and today, it shows 60 large-scale works across 105-urban-meets-pastoral-acres.

RELATED : What to Do in Chicago Now

Lake Geneva, Wisconsin

1.5 hours by car from Chicago

Give us a few days in Lake Geneva and we’ll spend the first at Black Point Estate and Gardens , an 1888 Queen Anne-style summer home that once belonged to Chi-Town brew mogul Conrad Seipp. Today, visitors come to relax on wicker chairs lining the wrap-around porch, explore the cottage's collection of Victorian furnishings, and stroll through its intimate gardens. To catch a glimpse of the resort town's other waterfront estates, walk a portion of the 21-mile-long, shaded Geneva Lake Shore Path . When it's time for dinner, off to Oakfire you should go. Start with imported burrata paired with grilled crostini before moving on to a wood-fired pizza— say, the Sorrento with arugula, shaved parmesan, mozzarella and prosciutto. There's also a bambini menu if you're day-tripping with picky kiddos.

Milwaukee, Wisconsin

Ask anyone about Milwaukee's major claim to fame and they'll likely tick off a laundry list of beer manufacturers—Schlitz, Pabst, and Miller among them. If you're looking for a beer-centric trip, there are always the typical tours and tastings, but might we suggest checking out a beer baron's Renaissance Revival-style estate? The Pabst Mansion is right downtown, full of Captain Pabst and his wife Maria's personal art collection as well as all the PBR merch you could ever want. For a different taste of the city, hit up the Milwaukee Public Market , where artisanal producers and demo kitchens serve everything from vegan Indian to made-to-order sushi.

RELATED : The Weekender's Guide to Chicago

Galena, Illinois

Galena may be a little bit of a hike from Chi-Town, but its charming, historic, quaint downtown feel (the population rings in at under 4,000) and chocolate-dipped cones from the American Old Fashioned Ice Cream Parlor (the vintage black-and-white awning is unmistakable) make it well worth the scenic drive. Main Street is the shopping thoroughfare of choice, so stick around long enough to bob in and out of its historic brick buildings housing a hundred or so boutiques, galleries, and cafés. Afterwards, head to the Blaum Bros. Distilling Co. and Cocktail Bar for a tour and a snarky drink like the Billy Fitz ("It's like Wrestlemania in a glass") with gin, fresh lemon, simple syrup, and lavender bitters before chomping down on some poulet roti or other German/French bistro-style grub at the husband-and-wife-run Fritz and Frites .

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10 Easy Weekend Getaways from Chicago—No Flights Required

Escape chicago for a few days with one of these 10, drivable weekend getaways and short road trips starting in chicago..

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Door County, Wisconsin, is one of the many easy-to-reach day trip destinations from Chicago.

Photo by Bailey Berg

Despite cries about that winter weather, Chicago is inarguably blessed with a little something we like to call location, location, location : With prime real estate on Lake Michigan, the Midwest city is about as far by car from Minneapolis (six hours) as it is Toronto (eight hours) and Nashville (seven hours). In this sense, it’s an ideal jumping-off point for a drivable trip. There are several weekend getaways from Chicago, whether you want to put some serious miles on your car or be somewhere new by the time your kids are done watching Cars. Read on for ten easy weekend getaway ideas from Chicago.

What cities are under three hours from Chicago by car?

• Milwaukee, Wisconsin (1 hour, 30 minutes)
• Madison, Wisconsin (2 hours, 25 minutes)
• Grand Rapids, Michigan (2 hours, 47 minutes)
• Peoria, Illinois (2 hours, 41 minutes)
• South Bend, Indiana (1 hour, 39 minutes)
• Indianapolis, Indiana (2 hours, 56 minutes)

The Dane County Farmers’ Market in Madison is one of the largest in the U.S.

Photo by MarynaG/Shutterstock

Geneva, Illinois

• Distance: An hour by car
• Best for: Singular art and great shopping

OK, OK. Geneva is technically a suburb of Chicago, but it feels worlds away, thanks to its small-town charm. Drop your bags at the boutique Herrington Inn & Spa , located on the Fox River, and set out to explore the city’s walkable downtown on foot. Public art abounds here, as do independent shops and restaurants (all told, there are more than 150 of them in the historic district).

Michigan City is a breath of fresh air not far away.

Photo by Andy Konieczny / Shutterstock

Michigan City, Indiana

• Distance: An hour and a quarter by car
• Best for: Hiking (and swimming for the brave)

On a clear day from Michigan City, you can see Chicago’s skyline across the water. Enjoy towering sand dunes, the cool waters of Lake Michigan, and nearly 50 miles of trails at Indiana Dunes National Park ; in Michigan City proper, attractions include the 19th-century Barker Mansion —listed on the National Register of Historic Places—and family-friendly Washington Park Zoo .

A lighthouse in New Buffalo, Michigan

Photo by Suzanne Tucker/Shutterstock

Harbor Country, Michigan

• Best for: A beach and wine combo trip

Comprising the eight towns of Michiana, Grand Beach, New Buffalo, Three Oaks, Union Pier, Lakeside, Harbert, and Sawyer, Harbor Country is a favored weekend escape from the Windy City, thanks to its beach and country offerings. There are also a number of world-class wineries and breweries in the area, including the popular Lehman’s Farmhouse and Dablon Vineyards and Winery , in nearby Baroda.

Milwaukee is home to one of the largest German populations in the U.S.

Photo by Jayne Lipkovich / Shutterstock

Milwaukee, Wisconsin

• Distance: An hour and a half by car
• Best for: Brats and brews

Milwaukee has a rich German heritage, which means the city is full of places to get a good beer and brat (and more beer, if that’s your thing). Both Pabst Blue Ribbon and Miller are based here, but don’t sleep on the smaller guys, including Milwaukee Brewing and Lakefront .

Mary stands atop the Golden Dome of the University of Notre Dame Main Administration Building.

Photo by Jonathan Weiss/Shutterstock

South Bend, Indiana

• Distance: An hour and forty minutes by car
• Best for: Whitewater rafting

There’s more to South Bend than Fighting Irish football, though we absolutely cosign the idea of a walk around Notre Dame’s scenic campus. Hit the rapids on East Race Waterway , North America’s first artificial white-water course, which cuts through the city, or visit the historic Robinson’s department store to throw your own pottery at the Pigeon and the Hen . Play arcade games—for free!—at the Garage Arcade and Bar , which has all the classics, Galaga and Ms. Pac-Man included.

The Fredrick Meijer Gardens spans 158 acres and features a host of outdoor art exhibits.

Photo by SNEHIT PHOTO / Shutterstock

Grand Rapids, Michigan

• Distance: Around three hours by car
• Best for: Beer, of course, but also outdoor sculptures

Voted “Beer City USA” in several national polls, Grand Rapids is known for its suds: Check out the Beer City Ale Trail , a map showcasing all of the options in the city. For food, we’re partial to strolling Downtown Market , which counts more than 20 vendors in the hall south of Heartside Park (a perfect picnic location, if you ask us). For an outdoor experience that requires a bit more activity, head to the 158-acre Frederik Meijer Gardens & Sculpture Park : here, you’ll find art by Auguste Rodin as well as a hall dedicated solely to carnivorous plants.

A dinosaur breaks out of the Children’s Museum in Indianapolis.

Photo by James Kirkikis/Shutterstock

Indianapolis, Indiana

• Distance: Three hours by car
• Best for: Museums, both traditional and quirky

Indianapolis is an incredible museum city. Although two of its most popular attractions are the Children’s Museum and the sprawling indoor-outdoor Indianapolis Museum of Art , don’t miss some of the city’s quirkier options: the Indiana Medical History Museum (not for the faint of heart) and the Kurt Vonnegut Museum and Library . Visit Indy’s famed City Market to sample more than 25 locally owned eateries; when you’ve had your fill, descend underground on a public catacombs tour, which takes place on the select Saturdays, May through October, between 10 a.m. and 3.15 p.m. (Private tours can be booked with Indiana Landmarks .)

Ann Arbor is known for its university, but a host of delights awaits all visitors.

Photo by Dark Vader / Shutterstock

Ann Arbor, Michigan

• Distance: Around three hours and 45 minutes by car
• Best for: Adventures on the river

Activities for all seasons abound in Ann Arbor, best known as the home of the University of Michigan. Tube, kayak, SUP, or canoe down the peaceful stretch of the Huron River—accessed from the 69-acre Gallup Park—or stroll U of M’s famed Matthaei Botanical Gardens and Nichols Arboretum . Be sure to make time for the city’s Kerrytown Market and Shops , a picturesque neighborhood full of independent boutiques and restaurants. ( Zingerman’s Deli , one of the best spots in Ann Arbor for a sandwich, is here.)

An aerial view of Door County, Wisconsin

Photo by Matt Sampson Photography/Shutterstock

Door County, Wisconsin

• Distance: Four and a half hours by car
• Best for: Exploring rugged coastline

A 70-mile-long peninsula, Door County is often called the “ Cape Cod of the Midwest” —and rightfully so. Just 50 miles northeast of Green Bay, Door County has stunning coves, cherry orchards, harbors, lighthouses, wineries, and some 300 miles of coastline. Newport State Park is an International Dark Sky Reserve , and the 900-acre Rock Island State Park has no cars; for a dose of small-town charm, stop by Ephraim, a Scandinavian-style village .

Traverse City might be a bit further away, but it’s worth the drive—especially in the fall.

Photo by Gary R Ennis Photos / Shutterstock

Traverse City, Michigan

• Distance: Five hours by car
• Best for: Exploring shops and galleries in a justifiably popular small town

No wonder Traverse City was named one of the sweetest small towns to visit in summer : a lakeshore beauty with art deco architecture, the city is beloved by many Chicagoans (including Oprah herself). One of Traverse City proper’s most popular attractions is the Village at Grand Traverse Commons: a hospital complex from the 19th century, the historic venue has since been reborn into a mixed-use space, with shops, restaurants, footpaths, and art galleries. Northwest of Traverse City is Leelanau Peninsula, which is home to the striking Sleeping Bear Dunes National Lakeshore .

Where can I go by train from Chicago?

No car? No problem. You can get virtually anywhere from Chicago by train: Memphis is 10 hours by rail; Seattle is 46. But for a weekend getaway, we’re partial to these picks:

• Indiana Dunes National Park (the South Shore Line from Chicago’s Millennium Station stops at four stations in the park )
• Milwaukee, Wisconsin (about 90 minutes by Amtrak from Chicago’s Union Station)
• Kalamazoo, Michigan (about two hours by Amtrak from Chicago’s Union Station)
• Grand Rapids, Michigan (about four hours by Amtrak from Chicago’s Union Station)

Of course, there’s plenty to do in Chicago itself before you head off; it was ranked number 2 in the best cities in the U.S. for 2023 , after all, thanks to its top restaurants , world-class museums, and abundant hotel options. On the other hand, if you’re feeling really adventurous, you could always take the ultimate epic road trip: 2,448 miles all the way to Santa Monica , California.

Happy weekending.

This article originally appeared online in 2020; it was most recently updated on August 31, 2023, to include current information.

• 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.

The Ultimate Weekend Trip to Chicago

Chicago is truly the gem of the Midwest . Perched on the scenic shores of Lake Michigan, the Windy City is a stunning metropolis that seems a bit out of place amongst the Great Plains. From world-renowned architecture to an iconic food scene, Chicago feels closer to New York than to Illinois (but don’t let the locals catch you making that comparison). Although there’s a seemingly endless variety of things to discover here, you can absolutely see the best of Chicago on a weekend trip. This guide will cover all the essentials for planning your Chicago getaway – including the best things to do, the best time to visit, and how to get around the city.

This is your guide to a weekend trip to Chicago, Illinois.

Getting to chicago.

There are two major international airports in Chicago – O’Hare (ORH) and Midway (MDW). O’Hare is the largest, but both are international airports.

To get from the airport to downtown Chicago, I highly recommend taking the ‘L’ (Chicago’s public transport system). It will be much more affordable than a taxi or Uber, and it’s also pretty convenient. Just follow the signs in the airport to the CTA train and purchase a ticket from the kiosks at the entrance. You can also use the ‘tap to pay’ function on your phone to get through the barrier rather than purchasing a physical ticket. There’s just one line operating to and from each airport (the blue line for O’Hare and the orange line for Midway), so you don’t have to worry about getting on the wrong train – they’re all the same when leaving the airport.

Getting Around Chicago

If you can avoid it, I do not recommend renting a car while in Chicago. You’ll spend way too much time in traffic and trying to find parking. Luckily, Chicago is pretty easy to navigate by other means, so a car is completely unnecessary for a weekend trip.

The “L”

The “L” (short for “elevated”) is Chicago’s train system and is the main source of public transportation. The (mostly) above-ground train (there’s one line that runs underground like a traditional subway) is an affordable and convenient way to get around the city.

NAVIGATION TIP: I love the app Citymapper for navigating public transport in a new city. It will help you know what line to take, where the nearest station is, and what stop to get off at.

As long as you’ve got good weather (i.e. it’s not mid-winter), walking is one of the best ways to explore Chicago. The city is relatively flat with paved sidewalks, so you’ll see plenty of locals and tourists alike getting around on foot.

If the “L” doesn’t have a stop near where you’re headed, and walking isn’t feasible, rideshare is probably the way to go. Uber and Lyft both operate in Chicago and are widely available.

Is Chicago Safe?

From the days of Al Capone to modern crime statistics, Chicago has, unfortunately, garnered a bit of a notorious reputation. While I can’t deny the stats, I can say from experience that I have yet to feel or witness anything unsafe throughout my (many) visits to Chicago. The areas that you’ll be exploring as a tourist are generally very safe overall. That being said, use common street smarts, travel with a companion (if possible), and keep valuables in a safe place.

Riding the L is also generally safe, but if you’ll be out past midnight consider using Lyft or Uber instead. If you’re alone at night and need to take the L, sit in the front car nearest the conductor.

Best Time to Visit Chicago

SUMMER June through August are the warmest and most popular times to visit Chicago. This is when you’ll see the highest hotel prices and largest crowds at popular tourist destinations like Millenium Park. Chicago really comes alive in the summer, but keep in mind that the heat and humidity can get overwhelming. For cooler weather and fewer crowds, aim to visit in early June.

AUTUMN Summer gets all the hype, but I think autumn is really the best time to see Chicago. The weather is generally comfortable, there are fewer crowds, and the colors (particularly around Grant Park) are lovely.

WINTER Christmastime in Chicago is magical with lights, festivals, and decorations all throughout the city. Bonus: winter is the low season in Chicago, so you’ll see fewer crowds and lower prices at hotels. Weather in December can be a bit of a gamble, but I think it’s worth it if you’re looking for a Christmas getaway. The rest of winter, however, can be downright brutal. With heavy winds, unbearably cold temperatures, and plenty of snow, avoid visiting from January through March.

SPRING Spring is short but gorgeous in Chicago. Tulips bloom along Michigan Avenue and parks burst with cherry blossoms. Expect a chance of rain, and don’t be surprised if you experience some unseasonably cold temps (particularly in early April).

The Windy City

Nicknamed the Windy City, a lot of visitors think the weather in Chicago must be…well, windy.

While, yes, Chicago does get windy at times, the nickname doesn’t have anything to do with the weather. The moniker instead comes from New York and Cincinnati journalists who editorialized that Chicago politicians were “full of hot air” or “full of wind”.

Where to Stay in Chicago

There are countless hotel options throughout Chicago for all budgets. While I often use sites like AirBnB or Vrbo when traveling, I always opt for a hotel when visiting Chicago. They tend to be much more conveniently located near attractions and L stations. These are a few of the best areas to book your stay.

Centrally located, this is the most popular and most convenient place to stay in Chicago – especially if you’re a first-time visitor. You’ll be within walking distance of Millenium Park, the Magnificent Mile, the Theater District, the Riverwalk, and more.

River North & Streeterville

This is a great neighborhood to stay in if you’re looking for a more budget-friendly option that’s still close to the action. With fewer L stations, the location is a little less convenient than The Loop, but it’s still centrally located. River North is closer to great restaurants, while Streeterville will put you next to Lake Michigan, Navy Pier, and the Magnificent Mile.

If you’re coming to Chicago solely to eat, station yourself in the West Loop. This is where you’ll find a lot of Chicago’s most trendy restaurants. It’s a little removed from the major Chicago attractions, so this neighborhood is better if you’ve already visited the city before.

Gold Coast or Old Town

These neighborhoods are also better for those who have visited Chicago before and are looking to explore beyond the main highlights. Both are on the north end of the city near the Lincoln Park Zoo, but each has its own qualities. Gold Coast is an affluent neighborhood brimming with historic mansions, designer boutiques, and acclaimed restaurants. Old Town is a bit more lively with restaurants, comedy clubs, and neighborhood haunts.

Second City

The city so nice, they built it twice.

Another common nickname for Chicago with misunderstood origins is Second City. No, it doesn’t mean that Chicago is “second best” (though many New Yorkers might like to think that’s the case). It got this name because the city has been built twice. After the Great Chicago Fire, the city was rebuilt atop the ruins to become the Chicago that you know today – the Second City.

Best Things to Do on a Weekend Trip to Chicago

Take an Architecture Cruise

The best way to see the renowned architecture of Chicago is by boat. In fact, taking an architecture cruise is the number one thing my local friends recommend for visitors. There are a number of cruise options, but my favorite is the original from Wendella Boat Tours . It’s a great way to learn more about the city as well! I promise you’ll find this cruise entertaining even if you’re not an architecture buff.

Enjoy the scenic Chicago Riverwalk

If you can’t enjoy the river views by boat (or even if you can), then certainly check out the Chicago Riverwalk. The 1.25-mile walkway will take you all the way from the city center to the Lake Michigan waterfront. Along the way, you’ll find restaurants with riverside patios, public art, and even a museum all about the Chicago River and its movable bridges.

Lakefront Trail & Milton Lee Olive Park

The only thing better than the view of the river in Chicago is the view of Lake Michigan. If you’ve never visited one of the Great Lakes before, be prepared to be stunned. The lake is so vast, standing on the coastline you could almost swear you were at the ocean. Lakefront Trail along the shore is the perfect spot for a walk, and Milton Lee Olive Park offers some gorgeous views of both the city skyline and Lake Michigan.

North Avenue Beach: If you’re able to venture out a little further, this beach is another gorgeous option for visiting the lakefront. This is a popular spot for photos, and it’s easy to see why. The views of the city skyline across the lake are particularly beautiful around sunset.

Sample some of Chicago’s famous foods

When you think of Chicago, what do you think of? If “pizza” wasn’t one of the first words to come to mind, we might not be talking about the same city. Chicago is home to a number of delicious dishes, including its famed pizza, and you should definitely sample as many things as you can while you’re here. These are a few to put on your list:

• Deep-dish pizza from Pequod’s Pizza (if you’re vegan, check out Gino’s East or Kitchen 17 instead).
• Tavern-style pizza (the style typically preferred by locals) from Vito & Nick’s .
• Italian Beef from Al’s Italian Beef .
• A Chicago dog with everything (I like Devil Dawgs ), and don’t you dare order ketchup.
• A burger from Au Cheval (or the more casual Small Cheval ).
• Chicago-style popcorn from Garrett’s .

Visit “The Bean” at Millenium Park

No first-time visit to Chicago is complete without a visit to Cloud Gate, aka “The Bean”. The reflective art installation is beautiful against the backdrop of the city. Once you’ve snapped your share of photos, take some time to explore the rest of Millenium Park and the connecting parks as well.

The Bean is one of the top destinations in Chicago, so if you’re looking to avoid crowds, get there early or visit in the winter (brrr).

See Buckingham Fountain in Grant Park

Not far from Millenium Park is Grant Park, and the crown jewel here is the stunning Buckingham Fountain. It’s huge! If you have a little more time during your weekend trip, definitely make a stop at the Art Institute of Chicago nearby as well.

This may seem obvious, but do note that if you visit during the winter the fountain won’t be running.

Enjoy stunning views from an observation deck

The Skydeck at the Willis Tower (formerly known as the Sears Tower) is one of the most iconic ways to see the city from above. On a clear day, you can see up to four states, and the glass floor enables you to see straight down from the top of the tower.

While the Willis Tower is the most popular, I love the 360° Chicago views from the Hancock Tower near the waterfront. The observation deck offers 360° views of the city (skip the extra cost for the “Tilt” option that tilts you outward over Michigan Avenue – it’s really not worth it).

HOT TIP: Skip the expensive entrance fee at the Hancock Tower and head up to The Signature Lounge on the 96th floor instead. You’ll have to buy a drink, but it’ll be a fraction of the price of visiting the observation deck (and it’s actually a floor higher than the observation deck).

If rooftop bars are more your speed, Chicago has spectacular options. Cindy’s near Millenium Park is probably the most renowned – both for the menu and the views. Another beautiful option is the rooftop at London House along the river. Both book up quickly though, so be sure to grab reservations in advance.

Take a ride at Navy Pier

Truthfully, Navy Pier is one of my least favorite places to visit in Chicago (it’s just ultra touristy and always crowded when the weather’s nice). If it’s your first visit to Chicago though, you have to see the Ferris wheel on the pier – it’s just so iconic. Better yet, ride the Ferris wheel! It’s a lovely and relaxing way to take in the city.

Go window shopping on the Magnificent Mile

The stretch of Michigan Avenue known as the Magnificent Mile is Chicago’s premier commercial district. It’s home to upscale shops, posh hotels, beautiful old buildings, and even the largest Starbucks Roastery in the world (it’s four floors plus a rooftop).

Take a walk around Gold Coast

The quiet, tree-lined streets of Gold Coast make up Chicago’s most exclusive neighborhood. Here you’ll find multi-million dollar brownstones alongside historic mansions (including the original Playboy mansion). It’s a beautiful place to grab a coffee and go for a quiet stroll.

Visit some of Chicago’s best breweries

Chicago has a burgeoning micro-brewery scene. The most well-known is probably Goose Island which has two locations in Chicago. There are great breweries all throughout the city, but the West Loop is probably the best neighborhood for brewery hopping.

Catch a Comedy Show

The comedy scene in Chicago is legendary. It’s home to The Second City , the iconic improv venue that brought us stars like Tina Fey, Steve Carrel, Chris Farley, Stephen Colbert, Tim Meadows, and countless others. Chicago is also the hometown of comedy greats like John Belushi, Bill Murray, and John Mulaney. As such, there are few things more memorable than catching a comedy show in Chicago during your weekend trip. Aside from the aforementioned Second City, other great spots include the historic Zanie’s and the famous Laugh Factory .

Discover Chicago’s Notorious Mobster Past

Thanks to the likes of Al Capone, Chicago’s history is irrevocably tied to prohibition-era mobsters. To learn all about it, join one of the many Chicago Gangster tours. If you’d rather skip the history lesson and just experience Chicago the way Capone did, make a stop at The Green Mill cocktail lounge for drinks and live jazz. The former speakeasy is well-known to have been frequented by Al Capone himself.

Whether you’re looking to eat your way through the city or to feast your eyes on some incredible scenery , Chicago has a lot to offer. A weekend trip to the Windy City will give you ample opportunity to discover the best of Chicago.

Have any questions about your upcoming trip to Chicago that I didn’t answer here? Let me know in the comments.

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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: 

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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… 

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20 Best Weekend Getaways from Chicago

Last Updated By VI on April 25, 2024 in Things to Do in Illinois & Places to Visit

Grand Geneva Resort - 1 hour 30 minutes from Chicago

Grand traverse resort - 5 hours from chicago, the abbey resort - 1 hour 40 minutes.

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Midwest Vacation Ideas: From Minneapolis , Ohio , MN , Iowa , From Detroit , Michigan

100 Grand Traverse Resort Village Blvd, Acme, MI 49610

269 Fontana Blvd, Fontana-On-Geneva Lake, WI 53125

Egg Harbor - The Newport Resort - 4 hours 30 minutes

7888 Church St, Egg Harbor , WI 54209

The Knickerbocker on the Lake - 1 hour 30 minute

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The Green Tree Inn - 4 hours 25 min

15 Mill St., Elsah IL, 618-374-2821

The American Club, Kohler - 2 hours 30 minutes

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Washington House Inn - 2 hours

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Sweethaven Resort - 1 hour 20 minutes from Chicago

9517 Union Pier Rd, Union Pier, MI 49129

Hawk Valley Retreat & Cottages - 2 hours and 45 minutes

2752 W. Cording Rd., Galena IL, 888-777-6016

Mansion Hill Inn for Couples - 2 hours 30 minutes

424 N Pinckney St, Madison, WI 53703, 608-255-0172

Vrooman Mansion - 2 hours

701 East Taylor St., Bloomington IL, 309-828-8816

Oakwood Resort, Syracuse, IN

Oakwood Resort, 702 E. Lake View Road, Syracuse, IN 46567, 574-457-7100

Farmers Guest House - 2 hours 45 minutes

344 Spring St., Galena IL, 815-777-3456

Foodies can visit Crane Orchards and Cider Mill, Fenn Valley Vineyards and Winery. There are also some historic attractions you can visit including the Felt Mansion, the Old Schoolhouse History Center and the Saugatuck/Douglas History Museum. --->

Elkhart Lake

Elkhart Lake in Wisconsin is an ideal getaway destination for all nature lovers and water sport enthusiasts, boasting crystal clear lake water and an abundance of activities suitable for all ages. You can choose from a variety of accommodation options which vary from up-market resorts and vacation rentals to getting back to nature at the Broughton March Park campground, where you can pitch a tent or park your RV.

Water sports are the most popular summer activity and if you do not have your own equipment you can hire everything you need to enjoy the lake from Osthoff Resort Water Recreation Rentals or at Victorian Village Resort. You can try your hand at canoeing, kayaking, water skiing or simply enjoying the beautiful lake-side scenery on a pontoon cruise. Ecology Outfitters Guided Silent Water Tours provide equipment and lessons for beginners. The lake is famous for great fishing - Inland Waters Fishing Guide Service or Jay's Guide Service will lead the way.

Back on dry land you can explore the shores by horseback with Camp Anokjig Trailrides, do a Backroads Bike Tour (or simply rent a cycle at the Osthoff Resort) or go hiking along an abundance of trails. Speed enthusiasts can watch motorsports or enjoy various adventure programs at Road America. In winter the emphasis changes to cross-country skiing, snowshoeing and snowmobiling.

Door County

Door County in Wisconsin is situated on a peninsula which juts out into Lake Michigan and boasts over 300 miles of shoreline with beaches, bays and inlets waiting to be explored. Sun worshippers have an astounding 53 public beaches to choose from and if you would like to go boating there are 12 marinas where you can launch your own craft or charter one.