places to visit within 5 hours of chicago

Places to visit about 5 hours from Chicago

The Short North

German Village

Over-The-Rhine

Williamstown (Kentucky)

Gateway Arch

City Museum

Pappy's Smokehouse

St. Louis Zoo

Forest Park

Cities 5 hours from Chicago

5 hours :   Vienna, IL

4 hr 59 min :   Frankfort, MI

4 hr 58 min :   Lorain, OH

4 hr 57 min :   Carbondale, IL

4 hr 57 min :   Iron Mountain, MI

4 hr 57 min :   Chippewa Falls, WI

4 hr 57 min :   Elyria, OH

4 hr 56 min :   Ottumwa, IA

4 hr 56 min :   Elizabeth, IN

4 hr 56 min :   Creal Springs, IL

4 hr 55 min :   French Lick, IN

4 hr 55 min :   Traverse City, MI

4 hr 55 min :   Oskaloosa, IA

4 hr 54 min :   Omaha, IL

4 hr 54 min :   Oberlin, OH

These are approximate driving times in a radius from Chicago, Illinois. Search for vacation spots within driving distance for a day trip or weekend getaway. There are many towns within the total area, so if you're looking for closer places, try a smaller radius like 4½ hours . If you're willing to drive farther, try 5½ hours .

Not sure where to go? Take a day trip from Chicago , or if you have more time you can explore weekend trips from Chicago , but make sure you also check road conditions around Chicago . Looking for small towns or communities around Chicago, Illinois? Get a full list of up to 500 cities nearby Chicago .

Change your settings:

RV campgrounds 5 hours from Chicago

Lake George Campsite

East Bass Lake Park

Sand Lake Park

Oak Beach County Park

KOA Campground Kimball

Cathcart Park Campground

Cardinal Center Campground

East Fork State Park

Hunnewell Access

Wilder Park

Camp Comfort

Colwell County Park

Lake Hendricks County Park

Great River Harbor Campgrounds

Chapman Park

State parks 5 hours from Chicago

Young State Park

Huron National Forest

Tawas Point State Park

Sleeper State Park

Port Crescent State Park

Mt. Gilead State Park

Alum Creek State Park

E.P. Tom Sawyer State Park

Angel Mounds State Historic Site

Wayne Fitzgerrell State Park

Mark Twain State Park

Lake Wapello State Park

Rock Creek State Park

Whitewater State Park

More cities around 5 hours away by plane

Here are more cities based on a flight circle radius of 5 hours. These cities are much further than the ones above since now we're looking at a 5 hour flight.

5 hr 4 min :   Santo Tomas, Colombia

5 hr 4 min :   Sitionuevo, Colombia

5 hr 3 min :   Sabanagrande, Colombia

5 hr 3 min :   Baranoa, Colombia

5 hr 3 min :   Malambo, Colombia

5 hr 3 min :   Puebloviejo, Colombia

5 hr 3 min :   Cienaga, Colombia

5 hr 2 min :   Soledad, Colombia

5 hr 2 min :   Galapa, Colombia

4 hr 58 min :   Guadalupe, Costa Rica

5 hr 2 min :   Barranquilla, Colombia

5 hr 13 min :   Capesterre-Belle-Eau, Guadeloupe

5 hr 1 min :   Puerto Colombia, Colombia

5 hr 13 min :   Saint-francois, Guadeloupe

5 hr 13 min :   Saint-Claude, Guadeloupe

Cities at a radius of

Travel time from Chicago, IL

cities within 1 hour of Chicago 1½ hours from Chicago places within 2 hours of me in Chicago explore 2½ hours from Chicago 3 hr radius map from Chicago 3½ hr drive from Chicago places within 4 hours of me in Chicago within 4½ hours of me in Chicago 5 hour drive from me in Chicago 5½ hour drive from Chicago within 6 hours of Chicago 7 hour drive from Chicago driving 8 hours from Chicago 9 hours from Chicago

Distance from Chicago, IL

cities within 10 miles of me in Chicago within 20 miles of me in Chicago 30 mile radius of Chicago 40 mile drive from Chicago located 50 miles from Chicago 100 mile radius from Chicago within 150 miles of Chicago 200 mile road trip from Chicago distance of 250 miles from Chicago driving 300 miles from Chicago 350 mile trip starting from Chicago 400 mile drive from Chicago drive for 450 miles from Chicago 500 miles from Chicago day trips from Chicago

Chicago, Illinois is located at latitude/longitude coordinates 41° 52' 41" N  /  87° 37' 45" W

Join my monthly email! Sign up

19 Awesome Road Trips from Chicago (with Timings)

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

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

Best Chicago Road Trips in Summer

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

Distance: as far as you can go

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

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

2. Illinois’ Great River Road

Distance: 3.5-hour drive

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

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

3. Lake Michigan to South Haven

Distance: 2.5-hour drive

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

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

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

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

4. Shawnee National Forest

Distance: 6-hour drive

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

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

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

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

Best Chicago road trips in Winter

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

5. Grand Rapids

Distance: 3-hour drive

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

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

6. Muskegon

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

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

7. Indianapolis

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

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

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

8. Boyne Mountain Resort

Distance: 5-hour drive

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

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

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

Your ESTA for the USA

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

9. Apostle Islands

Distance: 7-hour drive

Does driving over ice count as going off-road?

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

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

Day Road Trips from Chicago

10. lake geneva.

Distance: 1.5-hour drive

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

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

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

11. Harbor Country

Distance: 1-hour drive

Wind between the towns of Michiana, Grand Beach, Three Oaks, New Buffalo, Lakeside, Union Pier, Harbert and Sawyer. This Chicago road trip will have you hopping between wineries and breweries, not to mention the beach.

It’s so close to the city, but the sand dunes and soft grasses make it a wholly different world. 

12. Starved Rock State Park

Distance: 2-hour drive

Families and romantics will love Starved Rock State Park for reasons that include: 13 miles of hiking, 18 canyons, free entry and nature-surround lodge.

It’s a great location to unplug for a day as you hunt down natural rock pools, waterfalls and incredible moss-strewn glades. You can even visit in the winter for cross-country skiing and cuddles in front of expansive mountain views. 

13. Saugatuck 

Making up Lake Michigan’s “art coast of Michigan”, Saugatuck and its neighbours (Fennville and Douglas) are house dozens of art galleries!

Unique and LGBTQ+-friendly shops feature alongside artsy hubs to make it a super welcoming town. Of course, famous Oval Beach appeals with soft dunes and paddleboat rides too. From craft booze tours to fruit picking and corn mazes, it’s one of Chicago’s best road trips.

14. Elkhart Lake

I won’t spoil it for you but this 292-acre lake and nearby Kettle Moraine State Forest is truly a place to unwind from the crowds.

You can hike the epic Ice Age National Scenic Trail or bike down Old Plank Road Trail. Pumpkin patches, race-tracking and fishing are all inclusive!

Want a charming hideaway? This is it.

Road Trips 4 hours from Chicago

Want your road trips from Chicago for a special weekend? Then these Chicago road trips are only 4 hours away.

15. Ann Arbor

If you’re looking for an all-season destination, Ann Arbor is the perfect road trip from Chicago.

Huron River entertains with kayaking, paddle-boarding, tubing and swimming; Matthaei Botanical Gardens and Nichols Arboretum displaying beautiful foliage. Definitely spare some time for Kerrytown Market and Shops for all their indie offerings! 

16. Door Country

Also called ‘Cape Cod of the Midwest’, Door Country is a 70-miles-long basket of fun!

You’ll never get tired of exploring its orchards, coves, lighthouses and wineries. Away from the light pollution, Newport State Park offers stunning starlit skies while Ephraim is all the small-town charm you need. Just imagine – 300 miles of coastline.

You can reach Galena under 4 hours but I recommend taking your time. Pull up through scenic rolling hills to go back in time because the Galena Historic District is made up of cobblestone streets and over 1,000 buildings from the 19 th century.

For those non-history buffs, Chestnut Mountain opens as a ski resort in the winter; Stagecoach Trail and Apple River Canyon State Park are open year-round. 

18. Richland County

To really escape from people, Richland County is a rural road trip destination where you can bunk for the night. But away from the isolated and lush property of Candlewood Cabins are fields and hills that keep you outdoors all day.

The Ridge Road and Pine River Recreation Trail fulfils all your adventurous needs – where else would you find wildlife while biking over abandoned railroads?

You also have three rivers and five state parks within an hour’s distance, and the lovely 100-mile Lower Wisconsin River Scenic Byway for more driving way. 

19. Huron-Manistee National Forest

Michigan really surprises us again and again!

Along the peninsula is the expansive Huron-Manistee National Forest, one of the best road trips from Chicago if you are a nature enthusiast. A single paved road takes you through dense forest (beautiful in the fall) to parking areas so you can hike your way through the serene space or canoe on the rivers. 

Road trips from Chicago

Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.

Whether you’re taking the car out for an hour-long spin or you’re willing to buckle down for a few hours, you won’t be disappointed by the scenery along your journey or the fantastic destinations ahead. 

Related Posts:

• 7 Ways to Make the Most of Your Road Trip Budget
• Planning a Road Trip in the USA: 13 Best Routes!
• 57 Coolest Things to Do in Chicago for 2023
• Christmas Things to Do in Chicago in Winter: 21+…
• 14 Awesome Stops on a Chicago to New Orleans Road Trip
• 11 Unique Stops on the Drive from Chicago to Atlanta

Hi, I'm Vicky! I wrote this. You can find me on all the social media @VickyFlipFlop. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

One Comment

That’s no picture of Elkhart Lake

Leave a Reply Cancel reply

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

Sign me up for the newsletter!

Best Road Trips From Chicago

Top road trip destinations from chicago.

🚗 470 miles ⏱️ 6 hours, 20 minutes

Escape to the charming Mackinac Island, where horse-drawn carriages and bicycles replace cars, and historic Victorian architecture awaits exploration. Enjoy breathtaking views of Lake Huron and indulge in famous fudge as you relax in this idyllic island setting.

🚗 940 miles ⏱️ 14 hours

Journey through the rugged beauty of Badlands National Park, where dramatic landscapes and unique geological formations await. Hike through the otherworldly terrain and marvel at the stunning vistas.

🚗 470 miles ⏱️ 7 hours, 10 minutes

Explore the vibrant music scene and rich cultural heritage of Nashville, also known as the "Music City." From live performances to historic sites, Nashville offers a memorable experience for every visitor.

🚗 805 miles ⏱️ 12 hours

Experience the bustling metropolis of New York City, where iconic landmarks, world-class museums, and diverse neighborhoods await exploration. From Broadway shows to Central Park strolls, NYC offers endless adventures.

🚗 555 miles ⏱️ 8 hours, 30 minutes

Witness the awe-inspiring beauty of Niagara Falls, one of the world's most famous natural wonders. Experience the power of the falls up close on a boat tour or enjoy panoramic views from observation decks.

🚗 600 miles ⏱️ 9 hours, 30 minutes

Immerse yourself in the beauty of the Great Smoky Mountains, home to diverse wildlife, lush forests, and scenic hiking trails. Discover cascading waterfalls and historic sites amidst stunning mountain vistas.

🚗 650 miles ⏱️ 10 hours, 10 minutes

Explore the vibrant city of Toronto, where multicultural neighborhoods, iconic landmarks, and world-class attractions await. From the CN Tower to diverse cuisine, Toronto offers something for everyone.

🚗 935 miles ⏱️ 14 hours, 10 minutes

Visit the iconic Mount Rushmore and marvel at the monumental sculptures of four U.S. presidents carved into the granite mountainside. Explore the surrounding Black Hills region and discover its rich history and natural beauty.

🚗 670 miles ⏱️ 11 hours

Experience the political and cultural heart of the United States in Washington DC. Explore iconic landmarks such as the White House, Capitol Hill, and the Smithsonian museums, showcasing the nation's history and heritage.

🚗 760 miles ⏱️ 11 hours, 30 minutes

Step back in time in Philadelphia, where the founding of the United States comes to life. Explore historic sites like Independence Hall and the Liberty Bell, and savor Philly's famous cheesesteaks and rich cultural scene.

🚗 460 miles ⏱️ 7 hours

Discover the vibrant city of Cleveland, where a thriving arts scene, world-class museums, and scenic waterfront views await. Explore attractions like the Rock and Roll Hall of Fame and enjoy the city's culinary delights.

🚗 1,450 miles ⏱️ 21 hours, 30 minutes

Experience the natural wonders of Yellowstone National Park, home to geothermal features, wildlife, and stunning landscapes. Explore geysers, hot springs, and majestic waterfalls amidst the park's pristine wilderness.

🚗 940 miles ⏱️ 14 hours, 10 minutes

Immerse yourself in the vibrant culture and history of New Orleans, where jazz music, Creole cuisine, and festive celebrations await. Explore the French Quarter, enjoy a riverboat cruise, and indulge in delicious beignets.

🚗 560 miles ⏱️ 8 hours, 30 minutes

Discover the soulful sounds and rich history of Memphis, birthplace of blues, soul, and rock 'n' roll. Visit iconic attractions like Graceland, Beale Street, and Sun Studio, and savor the city's famous barbecue cuisine.

🚗 650 miles ⏱️ 10 hours

Escape to the scenic beauty of Asheville, nestled in the Blue Ridge Mountains. Explore vibrant arts scenes, historic architecture, and outdoor adventures, including hiking, biking, and waterfall chasing.

🚗 1,000 miles ⏱️ 14 hours, 30 minutes

Explore the Mile High City of Denver, surrounded by the stunning Rocky Mountains. Discover outdoor adventures, craft breweries, and cultural attractions, including the Denver Art Museum and Red Rocks Amphitheatre.

🚗 200 miles ⏱️ 3 hours

Experience family fun and outdoor adventures in Wisconsin Dells, known as the "Waterpark Capital of the World." Enjoy thrilling water rides, scenic boat tours, and picturesque hiking trails amidst natural beauty.

🚗 1,260 miles ⏱️ 19 hours, 20 minutes

Discover the rugged beauty of Acadia National Park, where rocky shorelines, forested trails, and scenic vistas await exploration. Experience outdoor adventures, wildlife viewing, and stunning sunrises atop Cadillac Mountain.

🚗 2,020 miles ⏱️ 29 hours

Experience the glamour and excitement of Los Angeles, where Hollywood dreams come to life. Explore iconic attractions, beautiful beaches, and world-class entertainment in this diverse and dynamic city.

🚗 1,180 miles ⏱️ 14 hours, 30 minutes

Discover the charming beauty and rich history of Savannah, Georgia, with its cobblestone streets, historic squares, and antebellum architecture. Explore museums, art galleries, and savour the city's renowned Southern cuisine.

🚗 415 miles ⏱️ 6 hours, 15 minutes

Experience the vibrant culture and natural beauty of Minneapolis, situated along the banks of the Mississippi River. Explore art galleries, bike trails, and world-class dining in this dynamic Midwestern city.

🚗 1,750 miles ⏱️ 26 hours

Experience the dazzling lights and non-stop entertainment of Las Vegas, where world-class casinos, extravagant shows, and vibrant nightlife await. Explore the iconic Las Vegas Strip and indulge in luxury experiences.

🚗 1,740 miles ⏱️ 25 hours

Discover the breathtaking landscapes and outdoor adventures of Zion National Park, where towering red rock cliffs and narrow slot canyons await exploration. Hike iconic trails and experience the park's natural beauty.

🚗 550 miles ⏱️ 8 hours, 10 minutes

Experience the entertainment capital of the Midwest in Branson, Missouri, where live shows, family attractions, and outdoor adventures abound. From music theaters to theme parks, Branson offers fun for all ages.

🚗 2,140 miles ⏱️ 33 hours

Discover the majestic beauty of Yosemite National Park, where towering granite cliffs, cascading waterfalls, and ancient sequoia trees create an unforgettable landscape. Explore hiking trails, wildlife viewing, and scenic vistas.

🚗 1,700 miles ⏱️ 25 hours

Experience the awe-inspiring beauty of the Grand Canyon, one of the world's most breathtaking natural wonders. Marvel at the vast expanse of the canyon and explore scenic viewpoints, hiking trails, and outdoor adventures.

🚗 1,060 miles ⏱️ 16 hours, 20 minutes

Escape to the sunny shores of Myrtle Beach, where miles of sandy beaches, thrilling attractions, and world-class golf courses await. Enjoy water sports, shopping, dining, and family-friendly entertainment along the Grand Strand.

• About Melissa
• _Charity & Small Biz Interviews
• -Chicago Suburbs Hiking

SOCIAL MEDIA

12 Super Road Trip Destinations from Chicago for Spring Break

Sunday, january 23, 2022.

12 Super Road Trip Destinations from Chicago Perfect for Your Next Adventure

With warmer days hopefully upon us soon, time is here to think about road trips! I am sharing a few of my favorites within a range of distances.  Happy trekking!

Within 3 Hours

Galena, Illinois: Downtown Galena enchants with one of the most beautiful historic districts in the USA. The bustling downtown full of shops, wineries, eateries and history beckons wanderers. Nearby hiking experiences are plentiful and treat to fantastic views of the Mississippi including from one of our favorites, Mississippi Palisades State Park . The Ulysses S. Grant is home is one of our favorites to tour and includes so many authentic family artifacts. While in Galena, wander over to nearby Dubuque, Iowa for a trip up the Fenelon Place Elevator. 

Madison, Wisconsin: Wisconsin's state capitol, Madison , unfolds an amazing opportunity for a family getaway. The Wisconsin State Capitol Building is striking and quite an interesting place to tour. Don't forget to step out on one of the balconies for a view. A plethora of hiking opportunities exist in and around the city including Lakeshore Nature Preserve, Blue Mound State Park, Devil's Staircase and Pheasant Branch Conservancy. Olbrich Botanical Gardens enchants in all seasons. Chazen Museum of Art, Madison Children's Museum and Wisconsin History Museum all add to any itinerary. We also love nibbling at the bakeries in Madison including Madison Sourdough and Batch Bakehouse. 

Quad Cities, Illinois and Iowa: The Quad Cities incorporates a number of Illinois and Iowa communities saddling the striking Mississippi River. A wealth of nature activities can be enjoyed including hiking and bird watching on Sylvan Island, at Black Hawk Historic Site, at Illiniwek Forest Preserve and more. Putnam Museum and Science Center, Figge Art Museum and Quad Cities Botanical Center offer more avenues of discovery. Don't forget to pick up ice cream at Whitey's or Lagomarcino's. For the over 21 crowd, hit the Quad Cities Ale Trail. We love the wealth of activities available and return to the Quad Cities again and again!

Within 6 Hours

Columbus, Ohio: Columbus has been one of our favorite cities to wander. We love German Village full of historic buildings and small businesses. Visiting Schmidt's Restaurant rewards with fabulous and authentic German fare. (My favorite is the German chocolate pie.) Museums include the Center of Science and Industry with a dinosaur gallery, Columbus Museum of Art and Central Ohio Fire Museum. We also enjoy visiting the Columbus Zoo and Aquarium which has one of the best African savanna experiences I have viewed.

Grand Rapids, Michigan:   Grand Rapids is home to one of my favorite botanical gardens and sculpture parks, Frederik Meijer Gardens & Sculpture Park. the grand scale sculptures are breathtaking and the gardens awe especially the Japanese garden. We also find the Grand Rapids Public Museum and Grand Rapids Art Museum fascinating. We usually pair a trip to Grand Rapids with a trip to Lake Michigan's shore often at Grand Haven. I am totally a beach lover in all seasons and often prefer spring for visits because there are fewer visitors. Rosy Mound Natural Trail in Grand Haven is one of our cherished nature highlights.

Hocking Hills, Ohio: Hocking Hills State Park in Ohio fascinates with a cache of unique hikes exploring canyons, caves, cliffs, waterfalls and much more. We love renting a cabin in the region for a little nature respite away from it all.

Louisville, Kentucky:   Louisville offers a great launching point for a Kentucky vacation. Museums including the Louisville Slugger Museum & Factory and Frazier History Museum present venues entertaining a range of interests. Churchill Downs is iconic. Louisville Mega Cavern bestows a venue for weaving through ropes courses and sliding along ziplines underground. The food scene includes so many of our favorites including Mark's Feed Store and Homemade Ice Cream and Pie Kitchen. The Camberly Brown and Seelbach hotels sweep you back to old hospitality. Of course, bourbon is a must for the 21+ crowd.

Shawnee National Forest: Shawnee National Forest in Southern Illinois welcomes travelers to unique hikes with unparalleled views. The forest includes a remarkable 289,000 acres of nature adventures to experience. Hiking, camping, horseback riding, biking, fishing, climbing, boating and more forge incredible nature experiences in some of the most unique settings of the Midwest.

St. Louis, Missouri:   St. Louis is an ideal location for a little getaway right along the mighty Mississippi River. The City Museum, St. Louis Science Center, St. Louis Zoo and St. Louis Art Museum among others inspire discovery. Of course, visitors must check out the Gateway Arch! Eating on 'The Hill' will treat you to fantastic Italian fare. You will also be near Cahokia Mounds where you can learn about the Mississippian Mound Builders. Additionally, you can head to St. Charles or Ste. Genevieve for a little French colonial history. When in St. Louis, one must also take an Anheuser-Busch Brewery Tour.  So many avenues of exploration make St. Louis a fabulous destination.

Within 8 Hours

Minneapolis and Saint Paul, Minnesota:   Minneapolis and Saint Paul have always been a favorite locale to visit. I love that there are spaces to admire nature right in Minneapolis and St. Paul including Minnehaha Falls, Chain of Lakes and Shadow Falls. Plus, there are tons of hiking opportunities nearby in Minnesota and Wisconsin. Mill City Museum and the Museum of Russian Art are two of my favorite museums in the Midwest. A walk along the Stone Arch Bridge and a peek at flour mill ruins provide an interesting look at Minneapolis. Como Zoo Conservatory in nearby Roseville treats to magnificent floral displays in all seasons. The region is populated with local microbrews adding tasting experiences.

Omaha, Nebraska: Perched along the Missouri River, Omaha offered us a wonderful starting point for a few nature adventures including Platte River State Park, Lewis and Clark Monument Park, Heron Haven and more. We loved walking around the Old Market, peeking into the Passageway and more. The city includes a wealth of museums such as the Durham Museum, Joslyn Art Museum, Omaha Children's Museum present a wealth of adventures.  For a truly unique scene, visit Hollywood Candy which not only delights with tons and tons of candy but includes a vintage pinball arcade, movie memorabilia, a '50s diner, vinyls and so much more!

Pittsburgh, Pennsylvania: Pittsburgh is a fantastic vacation choice for any season. The city's range of museums inspires any wanderer. The National Aviary is a wonder that should not be missed. Several rooms are free-fly, so you will have all sorts of interesting birds freely flying and roaming. Andy Warhol Museum, Heinz History Center, Carnegie Museum of Natural History and more will invite exploration. Don't forget to take the Duquesne Incline up to the top of Mount Washington for a view. We have to take in this view EVERY time we are in the city. Wander the Strip District for all sorts of foodie treats and shops. Hiking, river views and more will entice nature lovers. Every trip to Pittsburgh welcomes us to new experiences.

Post a Comment

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..

• Copy Link copied

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.

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

25 Weekend Getaways Near Chicago

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

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

Indiana Dunes: 54 miles southeast of Chicago

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

Lake Geneva, Wisconsin: 80 miles northwest of Chicago

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

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

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

Galena, Illinois: 163 miles west of Chicago

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

Mount Morris, Illinois: 100 miles northwest of Chicago

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

Cedarburg, Wisconsin: 113 miles north of Chicago

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

Bloomington-Normal, Illinois: 130 miles southwest of Chicago

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

Madison, Wisconsin: 147 miles northwest of Chicago

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

Rockford, Illinois: 90 miles west of Chicago

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

Fox River Valley, Illinois: 60 miles west of Chicago

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

Milwaukee: 93 miles north of Chicago

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

Amish Country, Indiana: 110 miles east of Chicago

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

Champaign-Urbana: 140 miles south of Chicago

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

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

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

Zion, Illinois: 50 miles north of Chicago

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

South Bend, Indiana: 95 miles east of Chicago

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

Turkey Run Inn, Indiana: 150 miles south of Chicago

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

Grand Rapids, Michigan: 175 miles northeast of Chicago

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

Elkhart Lake, Wisconsin: 150 miles north of Chicago

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

Lake Mills, Wisconsin: 125 miles northwest of Chicago

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

Glencoe, Illinois: 15 miles north of Chicago

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

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

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

Beloit, Wisconsin: 96 miles northwest of Chicago

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

Midewin National Tallgrass Prairie: 60 miles southwest of Chicago

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

Woodstock, Illinois: 60 miles northwest of Chicago

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

30 Delightful Road Trips from Chicago

If you’re looking to get away from the city, here are the best destinations for day trips and weekend road trips from Chicago.

Chicago’s location makes it an ideal place to get in the car and go, whether you live in the city or you make it your home base for some Midwestern exploration.

I’ve lived in Chicago and its suburbs for twenty years, and in the Midwest my entire life (except for a brief four years in my early twenties).

Let’s just say I’ve been to a LOT of towns, villages, cities, parks, etc., that are within easy driving distance from the Windy City.

And while I love Chicago (I even wrote a book about it ) and The Local Tourist began as a guide to the city’s River North neighborhood, sometimes even I just need to get away.

I’ve hand-picked some of my favorite Midwest road trips from Chicago. If you’re looking for delightful towns with delicious food and drink, boutiques and artisan shops, intriguing history, outdoor adventures, natural beauty, and so much more, you’re sure to find your perfect road trip from Chicago.

Road trips are the equivalent of human wings. Ask me to go on one, anywhere. We’ll stop in every small town and learn the history and stories, feel the ground and capture the spirit. Then we’ll turn it into our own story that will live inside our history. Victoria Erickson

Love travel quotes? Here you go!

There may be affiliate links in this post, which means we may get a small commission if you make a purchase. It’s at no extra cost to you and helps keep TLT free. Everybody wins!

Road Trips from Chicago

How to choose the best road trips from chicago.

How far will you drive for a weekend trip?

I asked that question of members of The Local Tourist Facebook group and their answers surprised me. The winning time was five hours, and second place was four hours.

Several of these road trippers would even drive eight hours for a weekend vacation!

Based on their input, and my own obsession with road trips, I’ve included some destinations that require a few hours behind the wheel.

I’ve also included places that are much closer. In fact, there are a few towns and cities that are technically suburbs of Chicago. Depending on your starting point, these destinations may provide more of a staycation than a vacation.

But hey – that’s what being a Local Tourist is all about, right?

I’m only including destinations that I’ve personally visited and enjoyed. Clearly, I need to spend more time in Ohio and Michigan.

For each road trip destination, I’ve included driving time. This assumes you’ll be driving interstates and won’t be avoiding toll roads. It also assumes no traffic.

Depending on when you leave for your weekend road trips from Chicago, traffic could increase times by at least an hour, so check Google maps or Waze before you go.

I’ve also included suggestions for places to stay, as well as links to each destination’s official Convention and Visitors Bureau, or CVB. These local resources are my travel planning not-so-secret weapon .

Ready to plan your road trips from Chicago? Let’s go!

Related: before you go, check out all my tips for planning a road trip .

10 Day Trips from Chicago

If you’re looking for a quick getaway or even a day trip, these locations are short road trips from Chicago and all within two hours of the Windy City.

Elgin, Illinois

Driving time: 1 hour

Known as the City in the Suburbs, Elgin, Illinois, is a relatively quick drive or an easy train ride from downtown Chicago. Its proximity makes it perfect for a day trip, but there’s enough to do that you’ll want to make a weekend of it.

A good place to start is downtown Elgin. Located right on the Fox River, it’s filled with public art and historic buildings.

Get the history of the area at the Elgin History Museum (pictured above).

You can also take a free self-guided walking tour of the Elgin Historic District.

Since that walking will make you hungry, grab a sandwich at Blue Box Café or head up to West Dundee for a burger and a pint at Emmett’s Brewing Co., an award-winning brewery.

Another one of the great things to do in Elgin is visit Lords Park and Zoo. On its grounds is the Elgin Public Museum, the only natural history museum in the Fox Valley.

Where to stay in Elgin, Illinois: Most of the hotels in Elgin are along the I-90 corridor. The Holiday Inn & Suites is one of the most highly rated accommodations near Elgin.

CVB: Explore Elgin Area, exploreelginarea.com

Indiana Dunes National Park, Indiana

One of our newest national parks is a short drive or train ride from Chicago. Established in 2019 , Indiana Dunes National Park is 15,000 acres along the southern shores of Lake Michigan.

There are over fifty miles of trails, making hiking Indiana Dunes National Park one of its top attractions. Hikers can traverse dunes, wetlands, prairies, rivers, and forests, all in one park.

There’s a fee to access the park: $15 per person (up to $25 per family group) and $25 per carload.

You could spend the entire weekend at the park. However, if you want a break, drive a little further east to Michigan City.

While the town is known for Lighthouse Place Premium Outlets, it’s also home to several museums, including the Old Lighthouse Museum.

Where to stay near Indiana Dunes State Park: Camping is available within the park itself, and there are several hotel chains in Michigan City .

CVA: South Shore Indiana, southshorecva.com

Harbor Country, Michigan

Driving time: 1 hour 15 minutes

Just across the border from Michigan City, Indiana, is Harbor Country.

The Red Arrow Highway takes you through eight small towns, each unique, each charming in its own away. Think boutique instead of big box, locally owned versus chain.

Outdoor enthusiasts will find everything from kayaking and paddle boating to fishing, surfing, and golf. Of course, you can also spend the day at the beach.

One of the biggest attractions is the number of Southwest Michigan wineries and breweries. The climate is very similar to Napa Valley, and the area’s known for its award-winning wines.

Where to stay in Harbor Country: You can find inexpensive hotels as well as private homes in New Buffalo, Michigan .

CVB: Harbor Country Chamber of Commerce, harborcountry.org

Kenosha, Wisconsin

Driving time: 1 hour 20 minutes

Kenosha is the fourth largest metro area in Wisconsin, as well as the fourth-largest city on the shores of Lake Michigan, and there are TONS of things to do.

It’s the home of the oldest operating velodrome in the country, a free dinosaur museum, historic restaurants, not one but two lighthouses, and you can still ride an electric trolley.

Start your visit at the Kenosha History Center for an overview of the area’s past. Then don’t miss the Dinosaur Discovery Museum or Kenosha Public Museum, both of which are free.

The Civil War Museum is an impressive look at Wisconsin’s role in the war.

A must-visit restaurant is House of Gerhard, featuring traditional German specialties. Another favorite is Franks Diner. Guy Fieri featured it on  Diners, Drive-ins, and Dives and it serves up tasty American cuisine with a side of sass.

Check out more reasons you should visit Kenosha, Wisconsin .

Where to stay in Kenosha: you can stay in Kenosha hotels that are conveniently located off I-94, or you can choose an historic inn like The Stella Hotel and Ballroom. For a great view, check out Wyndham Garden Kenosha, right on the harbor.

CVB: Visit Kenosha Wisconsin, visitkenosha.com

McHenry County, Illinois

Driving time: 1 hour 30 minutes

I lived in McHenry County, whose northern border is shared with Wisconsin, for five years and still found new things to do.

One of the most surprising aspects of the area is the sheer number of parks. The McHenry County Conservation District manages more than thirty conservation areas, and most of them have hiking trails.

There are also city and village parks, as well as two state parks within the county.

Another great thing about the area is the food. Oh, the food! There’s farm-to-table at 1776 Restaurant and Duke’s Alehouse and Kitchen, incredible Italian at 750° Cucina Rustica, rich encased meats at Richmond Brathaus, and the best custard anywhere at Julie Ann’s Frozen Custard.

All are local; all are family-owned; all are delicious.

McHenry County’s county seat is Woodstock, which you might recognize. It’s where Groundhog Day was filmed, and the town celebrates with their very own groundhog, Woodstock Willie.

You can even stay in the same bed and breakfast where Bill Murray’s character woke up again, and again, and again.

With the mouthwatering breakfasts served each morning at Cherry Tree Inn Bed and Breakfast, though, you won’t mind if the same thing happens to you.

Read more about why I love being a Local Tourist in McHenry County , and you will, too!

Where to stay in McHenry County: Cherry Tree Inn Bed and Breakfast , of course! Since there are only four rooms, if they’re full, you can find hotels in Crystal Lake , the largest town in the county.

CVB: Visit McHenry County, visitmchenrycounty.com

Starved Rock State Park

Head to Starved Rock State Park for a day of fresh air, physical fun, and outdoor adventure.

Located just 94 miles southwest of Chicago, the landscape is an unexpected tableau of bluffs, steep trails, and waterfalls. Since it’s on the Illinois River, there’s also fishing and boating.

You can bring a lunch to enjoy at the waterfront picnic area, or grab a bite to eat at the historic lodge.

Nearby Ottawa is a charming town with lots of creative chefs, so you can have the best of both worlds.

Where to stay in Starved Rock State Park: There’s a lodge at the park itself, but I personally prefer camping. Starved Rock has one of the best campgrounds in the Midwest .

Janesville, Wisconsin

Driving time: 1 hour 45 minutes

Located right off I-90, Janesville is an ideal weekend road trip from Chicago, especially if you like the great outdoors, art, and history.

The town’s tagline is “Wisconsin’s Great Outside,” and there are thirty miles of trails in Janesville, including a portion of Wisconsin’s Ice Age Trail. One of the most scenic treks is the mile and a half hike to Devil’s Staircase.

The Rotary Botanical Gardens is a non-profit garden covering twenty acres. You won’t want to miss their Holiday Light Show.

From Thanksgiving weekend through December, the gardens become a magical winter wonderland strewn with hundreds of thousands of lights.

History buffs will get a kick out of exploring Janesville’s thirteen historic districts. One of the highlights of any visit to Janesville would be the Lincoln-Tallman House.

Built in 1857, it’s been a museum since 1951. Eighty-five percent of the furnishings in the house are original, including the bed that Lincoln slept in when he was a guest.

Janesville’s dining scene is relatively new, but with restaurants like Genisa Wine Bar and the Sandwich Bar, it’s gaining steam and there are enough unique spots to keep your palate happy.

I definitely recommend bellying up to the 1933 Art Deco bar at O’Riley and Conway’s Irish Pub for some Scotch eggs.

Combine history and beer at Gray Brewing Co. They’ve been brewing beer since 1856, except during that pesky Prohibition when they turned to sodas. It’s one of the oldest family-owned breweries, not just in Wisconsin, but in the United States.

When you visit Janesville, make sure you’ve got your walking shoes and plenty of room on your SD card, because the town is filled with vibrant and colorful murals.

Where to stay in Janesville, Wisconsin: Renovated in 2019, the Hampton Inn provides comfortable rooms with modern décor. Breakfast is included, and it’s one of the better spreads I’ve seen.

When I stayed, the hot items were frequently replenished and there were several options including both waffles and mini-waffles.

CVB: Janesville Area Convention and Visitors Bureau, janesvillecvb.com

Lake Geneva, Wisconsin

Located just 75 miles northwest of Chicago on the other side of the Wisconsin border, Lake Geneva provides a year-round escape from hectic city life and is a short day trip from Chicago or great weekend destination.

One attraction with a direct tie to Chicago is the Yerkes Observatory (pictured above).

Yerkes is considered the birthplace of modern astrophysics and was funded by Charles Yerkes, who had a huge role in developing Chicago’s public transportation.

Lake Geneva has long been a playground for Chicagoans. In the late 1800s and early 1900s, it seemed that every wealthy Chicagoan built a mansion on the shores of the lake. Today, many of those mansions still stand.

The best way to see them is to take a boat tour, especially if you can ride along when they’re delivering the mail. Lake Geneva is one of the few places left in the country where mail is delivered by boat.

Another way to see the mansions is to walk the path that surrounds the lake. Like Chicago’s lakefront with its public beaches, Geneva Lake is surrounded by a trail that’s open to everyone.

The lakefront path is one of the most popular things to do in Lake Geneva .

One place you can only visit from a boat, unless you have physical limitations and can’t climb the many stairs from the dock, is Black Point Estate. This historic mansion has many ties to Chicago, including Jane Addams .

For something completely different, feed an ostrich. Safari Lake Geneva is a drive-through experience that allows you to feed giraffes, alpacas, elands, and emus.

An experience that’s both fun and tasty is taking a class at Lake Geneva Cooking School. Chef John teaches you how to make dishes you might never attempt on your own, and he pairs them with stellar wines.

Like many, during lockdowns he pivoted and fulfilled his dream of publishing a cookbook . I’ve made several recipes from it, and highly recommend it.

Golf is one of Lake Geneva’s biggest draws. During the winter months, you can ski, snowboard, snowshoe, and ice fish.

Where to stay in Lake Geneva: Technically located in Fontana on the west side of Geneva Lake, The Abbey Resort is a sprawling complex with beautiful rooms overlooking a marina.

They also have multiple pools and there’s often live music, either in the bar or outside during the summer.

CVB: Visit Lake Geneva, visitlakegeneva.com

Milwaukee, Wisconsin

Milwaukee, Wisconsin, is an urban getaway filled with culture and outdoor fun.

The instantly recognizable Milwaukee Art Museum is definitely worth visiting, and after you’ve browsed its collections you can take a walk along the lakefront.

For more art, book a room at Saint Kate The Arts Hotel . This astounding hotel is like staying in a work of art – because you are. It’s right downtown, providing easy access to the river walk.

Beer lovers will have a blast exploring Milwaukee’s breweries. Lakefront Brewery is known for its fun tours. Milwaukee Brewing Company and Mobcraft are also great places to visit.

There’s no beer at the Pabst Mansion, but you’ll still want to see Captain Frederick Pabst’s house, built in 1892. It’s a gorgeous Flemish Renaissance Revival mansion that’s on the National Register of Historic Places.

Fun fact: Captain Pabst earned his stripes with the Goodrich Line of steamships, which was based out of Chicago.

Another nautical stop is North Point Lighthouse. Built in 1888 high on a bluff, Frederick Law Olmsted himself designed the grounds. Chicagoans will recognize the famous landscaper’s name from the 1893 World’s Columbian Exposition and the University of Chicago, among others.

Olmsted also landscaped Lake Geneva’s Yerkes Observatory, which was part of the University until recently.

The Harley-Davidson Museum is another must-stop and be sure to dine at Motor, the on-site restaurant.

During the summer there are festivals just about every weekend, so check Visit Milwaukee’s events calendar to find out what’s happening.

And of course, make sure you have some cheese curds, brats, and beer.

Where to stay in Milwaukee: Saint Kate The Arts Hotel for a modern art experience, The Pfister Hotel for a dose of history, and Iron Horse for more industrial décor and easy access to the Harley-Davidson Museum.

CVB: Visit Milwaukee, visitmilwaukee.org

Lafayette, Indiana

Driving time: 2 hours

My grandparents lived in West Lafayette, Indiana, so I grew up visiting. However, it wasn’t until a few years ago that I actually explored the town. Boy, had I been missing out on a lot.

Known as the home of Purdue University, West Lafayette, and its sister city Lafayette, have history, art, culture, delicious food and drink, and a vital sense of community.

There are several places that make this a great place for a road trip from Chicago. One is the Haan Mansion Museum of American Art.

The mansion was originally built for the 1904 World’s Fair in Saint Louis. Now it’s in West Lafayette and is filled with impressionist paintings and historic furniture.

Another is SAMARA. Designed inside and out by Frank Lloyd Wright for Dr. John and Catherine Christian, it’s a nearly perfectly preserved example of Wright’s Usonian architecture.

Another fascinating spot is Prophetstown State Park, combining a landscape that’s distinctly Indiana with the history of the Native Americans who fought the settlers’ encroachment, and the farmers who eventually tilled the land. While there, visit the nearby Tippecanoe Battlefield.

I’ve got even more places to visit in Lafayette. These include not only places I’ve been, but also spots recommended by students at Purdue University. I’ve partnered with a 400-level travel-writing class since 2018, and many of their submissions are local to the college town.

See why you should visit Lafayette and West Lafayette Indiana

Where to stay in Lafayette, Indiana: Mr. TLT and I loved the cozy intimacy of Black Blanket Farms Bed and Breakfast . If they’re booked, Lafayette has a gazillion hotel options since it’s a college town.

CVB: Visit Lafayette-West Lafayette, homeofpurdue.com

9 Weekend Road Trips from Chicago between 2 and 3 hours

Shipshewana, indiana.

Driving time: 2 hours 15 minutes

If you’re looking for a slower pace, yet still want plenty to do, add Shipshewana to your weekend adventures.

Shipshewana is in LaGrange County, also known as Indiana Amish Country. You’ll know when you get close because you’ll start seeing horse-drawn buggies and bicyclists everywhere.

With the third largest Amish population in the world, this area is a definite departure from the hustle and bustle of city life. Instead, it’s antiques and hand-crafted furniture, delicious food, and fun entertainment.

One of Shipshewana’s most well-known attractions is the Shipshewana Flea Market . Begun in 1922 with a livestock auction, this family-owned business is the largest flea market in the Midwest.

Learn what it’s like to attend the Shipshewana Misc & Antique Auction .

You also don’t want to miss the Davis Mercantile . Another family affair, it’s a destination for dining, shopping, and riding the carousel.

If you plan your trip in advance, you might be able to dine in an Amish home, which is a real treat (and the best mashed potatoes ever). If it’s a last-minute getaway, The Blue Gate Restaurant is always a favorite. After dinner, head upstairs for a show at the theater.

Other fun things to do in Shipshewana include touring Cook’s Bison Ranch, exploring one of the many county parks, having dinner in an Amish home , canoeing or kayaking on the Pigeon River, and taking a driving tour on a hunt for barn quilts.

Where to stay in Shipshewana: The Blue Gate Garden Inn is a comfortable hotel that’s filled with amenities, including outdoor fire pits and an ice cream shop.

CVB: Visit Shipshewana, visitshipshewana.com

Sheboygan, Wisconsin

Driving time: 2 hours 30 minutes

When people ask me the destination that surprised me the most, Sheboygan, Wisconsin, tops the list.

I visited in August 2021, and it was my first press trip post-cancer. It was exactly the experience I needed: waves, beaches, amazing food, brilliant art, and a community that preserves its past.

Your first stop should be the Sheboygan Visitor Center. It is absolutely the coolest visitor center I’ve ever seen – and I’ve been to a lot.

Sheboygan’s known as the Malibu of the Midwest, so of course I had to get out on the water. One of my favorite things to do was take a first sailing lesson in Lake Michigan. That’s right – you can learn how to sail on a weekend trip to Sheboygan.

The Kohler name is prominent in the area. In addition to the manufacturing company and a nearby resort, there’s also the Kohler Arts Center and the Kohler Art Preserve, which opened in 2021.

Kohler also manages the James Tellen Woodland Sculpture Garden, one of several artist-built environments throughout the state.

History geeks will want to stop at Sheboygan Indian Mound Park and the Sheboygan County Historical Society and Museum.

For dining, don’t miss Black Pig, Il Ritrovo, and BoMallies. Breakfast should absolutely begin at Paradigm Coffee and Music. Best. bagel. sandwich. ever.

Check out my piece about this surprising place, and I’ve even included the perfect 3-day Sheboygan itinerary .

Where to stay in Sheboygan: Blue Harbor Resort offers gorgeous rooms and an even better view. They’ve also got a whole water park, on-site dining, and easy access to the beach.

CVB: Visit Sheboygan, visitsheboygan.com

Elkhart Lake, Wisconsin

About twenty minutes from Sheboygan is another delightful road trip from Chicago.

Elkhart Lake has all the feelings of a resort town. There are historic accommodations, unique boutiques, and delicious dining.

The eponymous lake is gorgeous, with crystal clear water. You can take a pontoon boat ride, or go kayaking or paddle boarding.

The village is also right by the Ice Age Scenic Trail and Kettle Moraine State Forest – Northern Unit, providing lots of opportunity for outdoor activities.

Racing fans won’t want to miss Road America. This four-mile road course is considered the best in the United States and one of the top in the world.

Not only can you watch racing, you can also take a spin around the track yourself. They offer both motorcycle and automobile driving schools.

Where to stay in Elkhart Lake, Wisconsin: Osthoff Resort is an historic inn that offers a variety of room options, including suites and villas, and features amenities such as an indoor and outdoor pool, spa, and fitness center.

The resort also has several dining options on-site, including a fine-dining restaurant and a casual bistro.

CVB: Elkhart Lake, visit website

Galena, Illinois

Driving time: 3 hours

Galena, Illinois, is located near the Mississippi River on the opposite side of the state from Chicago. Surrounded by the rolling hills and bluffs of the Driftless Region, it’s an area dotted with wineries and golf courses.

There are many reasons nearly a million people visit the former mining mecca each year. From shopping along its historic main street to the many wineries in the area, it’s a great spot for a romantic weekend or a girls getaway.

A stroll down Main Street feels like a step back in time. Be sure to stop into Galena Canning Company for a taste of salsas and jams, and Galena Brewing Company offers a lineup of tasty beers.

Thrill-seekers will love a visit to Long Hollow Canopy Tours , a zipline adventure through the woods.

Nature lovers can explore trails along the nearby Mississippi River, and golfers will love a few rounds at Eagle Ridge Resort & Spa.

There are also several historic buildings, and the Ulysses S. Grant Home is one of the most popular places to visit for a look into the past.

Where to stay in Galena, Illinois: While there are hotels that are closer to Galena’s historic Main Street, two of my favorites are a short drive from downtown. Goldmoor Inn Bed and Breakfast is an elegant getaway overlooking the Mississippi River.

Eagle Ridge Resort and Spa is my home away from home when I’m in Galena. I’ve stayed there at least five times. I love the variety of accommodations, activities, and the delicious food.

CVB: Visit Galena, visitgalena.org

Hendricks County, Indiana

My first visit to Hendricks County, Indiana, was in 2017, and since then I’ve returned four? five? times. You might say I like it. I even taught the first writing workshop for Midwest Travel Network (I’ve now taught three) at Natural Valley Ranch, a cabin with that private pond out its back door.

There are also horses, that you can ride. Squeee!

It’s a large county comprised of several towns. Some are large, like Plainfield and Avon, and others are small, like the tiny Lizton, which is home to the best barbecue – and pecan pie – in Indiana (and possibly the Midwest).

Race fans not only have easy access to the Indianapolis Motor Speedway, they can also see the NHRA Finals at the Lucas Oil Raceway within Hendricks County.

The only Doctor Who Museum and Store is in Hendricks County, as is the Tie-Dye Lab, where you can make your own tie-dye apparel. Beasley’s Orchard has the best apple cider. Oasis Diner is the only diner on the National Road and it’s got one of the best pork tenderloin sandwiches anywhere.

Basically, go to Hendricks County . There’s so much to do I bet you’ll want to go back again and again, just like I do.

Where to stay in Hendricks County: Natural Valley Ranch is great if there’s a big group of you exploring the area. If not, then I’m a fan of Staybridge Suites . Each room includes a kitchenette, plus they offer free breakfast and weekday happy hours.

CVB: Visit Hendricks County, visithendrickscounty.com

More Road Trips from Chicago between 2 and 3 hours

• Madison, Wisconsin; 2 hours 45 minutes
• New Glarus, Wisconsin; 2 hours 45 minutes
• Indianapolis, Indiana; 3 hours
• Quad Cities, Illinois/Iowa; 3 hours

11 Weekend Road Trips from Chicago between 3 and 5 hours

Fort wayne, indiana.

Driving time: 3 hours 10 minutes

When you go to Fort Wayne, go hungry. And thirsty. This northeastern Indiana town has a thriving food and beer scene that will have you coming back for more.

This All-American City is located at the confluence of three rivers, and that riparian location has fed its personality since it was founded when General “Mad” Anthony Wayne built a fort there in 1794. That fort didn’t last long, and by 1815 the town was on its third fort, built by Major John Whistler.

Chicagoans might recognize that name: he built Fort Dearborn when he was a Captain. You can visit a replica of Whistler’s fort, and they often have events.

One of the best things to do in Fort Wayne is visit the YLNI Farmers Market. This bustling marketplace features everything from handmade chocolates to hot sauces that’ll blow your top off to candles that smell like Fort Wayne (and Montana, Chicago, and everywhere else Simple Nature‘s creative creator has been). 

But what about that food, you ask? A few favorites include Club Soda, for white tablecloth dining with a side of live music, Birdie’s for shared plates in an airy rooftop, and Hall’s Prime Rib for down-home diner cooking.

Beer fans will want to belly up at Junk Ditch, The Hoppy Gnome, and Hop River Brewing Company.

Where to stay in Fort Wayne, Indiana: Courtyard Fort Wayne Downtown at Grand Wayne Convention Center is in a great location; across from the convention center and in between Parkview Field and Embassy Theatre.

CVB: Visit Fort Wayne, visitfortwayne.com

Green Bay, Wisconsin

Driving time: 3 hours 15 minutes

While it may seem blasphemous to some to suggest driving to the home of the Packers from the home of the Bears, I guarantee there’s a lot more going on than gridiron battles.

Auto enthusiasts will love The Automobile Gallery. Opened in 2016, this collection of pristine vehicles span over a century of automotive history.

From the iconic 1908 Cadillac Model T to the sleek 1960 Chevrolet Corvette, every car enthusiast will find something to admire.

The museum also features a rotating selection of vehicles, ensuring that there is always something new and exciting to discover.

For transportation of another kind, visit the National Railroad Museum. The museum began in 1956 and now covers a sprawling 33-acre campus.

Not only can you see locomotives like the iconic “Big Boy” No. 4017, you can step inside a Pullman sleeper car and learn about the porters who worked America’s rail lines.

Ready for a drink? From Captain’s Walk Winery to Zambaldi Beer, you’ll find something to whet your whistle.

And if you’re hungry, Green Bay will keep you fat and happy. (Speaking from experience here.) Don’t miss the authentic kringles at Uncle Mike’s Bake Shoppe or a cup of Booyah, a hearty Belgium chicken stew.

Where to stay in Green Bay, Wisconsin: Stay in the heart of Green Bay at the historic Hotel Northland . The hotel’s especially great for a romantic getaway.

CVB: Discover Green Bay, website

Dubuque, Iowa

Driving time: 3 hours 20 minutes

You’ll be glad Dubuque Iowa is one of these easy road trips from Chicago, because there’s so much to do you’ll want to return again and again.

Dubuque’s location on the Mississippi means it’s filled with river lore. Begin your visit at the Mines of Spain, a National Historic Landmark and Iowa State Recreation Area. It’s named for the mines that Julien Dubuque, the town’s founder, worked with permission from first the Mesquakie and then the Spanish. The Julien Dubuque Monument resembles a rook and overlooks the Mississippi; Dubuque is buried on the site.

Get an in-depth introduction to the river and the region at the National Mississippi River Museum and Aquarium, then go on the river itself. You can take a steamboat tour or an American Lady River Cruise aboard a yacht.

Like Janesville, Dubuque’s downtown is also covered with murals, and it’s a fun afternoon to walk the streets and find your favorite.

Dubuque’s most unusual attraction is the Fenelon Place Elevator. It’s the shortest, steepest railroad and a ride to the top provides some of the best views in the city.

Another spot for great views is Eagle Point Park. You’ll get a birds eye view of Lock and Dam #11 and can see into both Wisconsin and Illinois.

One of the most famous attractions is in nearby Dyer. The Field of Dreams Movie Site is surprisingly moving, especially now that you can tour the house. Inside you’ll discover stories behind the filming of this beloved classic.

I think the food scene in Dubuque will surprise you. It certainly surprised me to discover several innovative chefs serving quality cuisine. Make reservations for both Brazen Open Kitchen and Pepper Sprout and you’ll be one happy diner.

Where to stay in Dubuque, Iowa: since it’s right downtown, you can’t get much more convenient than Hotel Julien Dubuque . Plus, it’s a gorgeous hotel with oodles of history, including stories about Mr. and Mrs. Lincoln and a certain gangster from Chicago.

CVB: Travel Dubuque, traveldubuque.com

Brown County, Indiana

Driving time: 4 hours

Brown County, Indiana, is known for its beauty when the leaves change colors, but that doesn’t mean you can only visit in the fall. The rolling hills are beautiful year round.

While the area is easy to get to now, that wasn’t always the case. Its relative isolation fostered a vibrant artists community, which thrives to this day.

Visit Brown County and you can see the home and studio of one of the founding artists T.C. Steele. He was one of the five members of the acclaimed Hoosier Group. In the late 1800s, that group put Indiana’s art scene on the map, and Brown County in particular.

Browse the galleries of Nashville, Indiana, and you’ll see works of art from those early painters as well as artists of today.

Get a two-for-one cultural experience at Country Heritage Winery. Not only can you taste wines, when you take a weekend road trip from Chicago, you can do so while listening to live music.

Another favorite is Hard Truth Hills. Inspired by Sierra Nevada’s set-up in Asheville, North Carolina, this is a multi-purpose destination with a brewery, a distillery, a restaurant, and an outdoor stage. Pro tip: get the to-die-for pulled pork nachos.

Brown County is one of those places where you can choose to go-go-go, or you can kick back and relax. Either way, it’s definitely worth the drive.

Learn more about Brown County and how it became the tourist destination it is today.

Where to stay in Brown County: Abe Martin Lodge is located within Brown County State Park. Bring the kids and your swimsuits; they’ve got an indoors water park. Want something more secluded? There are cabins, too.

CVB: Brown County, browncounty.com

Sandusky, Ohio

Driving time: 4 hours 45 minutes

Sandusky is most famous for being the home of Cedar Point amusement park, but this city on the shores of Lake Erie is much more than roller coasters and funnel cakes.

A fun way to get an overview is to take a Segway tour. Sandusky Segwave offers guided tours through the historic downtown. Perched atop your personal transporter, you’ll glide past historic sites, through city parks, along the lakefront, and past the Merry-Go-Round Museum. You’ll learn about the town’s very beginnings, as well as its role in the Underground Railroad.

Another reason to visit Sandusky is Kelleys Island. Take a high-speed ferry to the largest American island in Lake Erie for a day of art, shopping, and wine.

While you’re on the island, don’t miss Glacial Grooves State Memorial. This National Natural Landmark protects the largest easily accessible grooves in the world. To see them is to witness the power of the glaciers that shaped North America.

Before you go back to Sandusky, get a scoop of Lake Erie Cookie Island Monster. It’s the official ice cream of Ohio’s Lake Erie Shores and Islands , Sandusky’s visitors bureau.

Warning: it will turn your tongue blue!

Check out my guide to see many more things to do on Kelleys Island .

Where to stay in Sandusky, Ohio: Hotel Kilbourne . This place puts the boutique in boutique hotel. In addition to being the only Sandusky hotel that’s on the water, it’s also got a rooftop bar and an on-site restaurant.

CVB: Ohio’s Lake Erie Shores and Islands, shoresandislands.com

Driving time: 5 hours, or as long as you’d like!

Route 66 epitomizes the freedom of the open road, and it begins in Chicago. The route became official in 1926, providing many small towns access to significant national roadways for the first time. Although it was decertified in 1985, the Mother Road lives on.

This scenic byway changed course over the years, and these alignments are well marked in Illinois. If you’re short on time, I-55 will take you from one attraction to the next, but the fun of driving one of the country’s most historic byways is in following its original path.

Some of the most popular roadside attractions include Buckingham Fountain (not technically on Route 66, but you’re so close!), the Gemini Giant, Bunyon’s Statue, and Carlinville’s Million Dollar Courthouse.

Route 66 in Illinois is only 301 miles, but it’s nearly a century of Illinois history, so take your time.

More road trips from Chicago between 3 and 5 hours:

• Iowa City, Iowa; 3 hours 45 minutes
• Door County, Wisconsin ; 3 hours 50 minutes
• Bloomington, Indiana ; 4 hours
• Spencer, Indiana : 4 hours
• Collinsville, Illinois and Cahokia Mounds State Historic Site : 4 hours 45 minutes
• Traverse City, Michigan; 4 hours 55 minutes

Want an epic trip from Chicago but don’t feel like driving? Consider a train to Seattle – here’s what it’s really like to ride the Amtrak Empire Builder !

Map of Road Trips from Chicago

I hope these delightful road trips from Chicago will help you find someplace wonderful to visit for your weekend getaways. Each place is special and offers unique experiences. When you go, I’d love it if you’d share your photos in our Facebook group .

Oh, and be sure to bookmark this page, because I’ve got more destinations to add!

Protect Your Trip »

24 Top Weekend Getaways From Chicago

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

Getty Images

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

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

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

Best Weekend Getaways from Chicago:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[Read: The Best Midwest Vacations for Families .]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

You might also be interested in:

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

Tags: Travel , Midwest Vacations , US Vacations

World's Best Places To Visit

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

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

You May Also Like

Swimming with pigs in the bahamas.

Amanda Norcross May 2, 2024

The 15 Best Chicago Tours for 2024

John Rodwan May 1, 2024

The 10 Best Harry Potter Tours in London

Marisa Méndez April 30, 2024

12 Cheap Fourth of July Getaways

April 29, 2024

The Best Tours of Buckingham Palace

Laura French April 29, 2024

Flight Canceled or Delayed? What to Do

Amanda Norcross April 26, 2024

The Best Beach Hats

Megan Johnson and Sharael Kolberg April 26, 2024

The Best Florence Tours

John Rodwan April 25, 2024

The 9 Best Louisiana Swamp Tours of 2024

John Rodwan April 24, 2024

How Much Does a Cruise Cost?

Gwen Pratesi April 24, 2024

Your Family Will Love These 30 Road Trips Near Chicago

• Updated: 04/03/2024

Chicago and US Midwest families, we feel you. Airplane tickets are pricier than ever. Though, your need for a getaway has never been greater. 

You want to get out of town with minimal effort and do not want to spend a small fortune to do it. 

To help, I share my favorite short to medium-distance driving destinations and those recommended by regional experts—other travel bloggers and planners passionate about places in the Midwest. 

Together, we came up with this list of the 30 best road trip destinations for the summer and the fall, from big cities to small charming towns to blow-you-away natural wonders, all within a five-hour drive of Chicago.

Table Of Contents

Check out our destination recommendations by state below. 

• Michigan & Ontario

Or view all 30+ places we recommend going in the map below.

How to use this map:  In the map header, click the square tab to the left of my logo or click the enlarge frame to the right to view detail. You can save the map to “Your Places” on Google Maps by clicking the star next to the map name. Or you can share it by clicking the share icon.

Wisconsin: Top Road Trips Within 5 Hours of Chicago

Welcome to Wisconsin, or the “Dairyland State,” loved by visitors for its rich dairy heritage, delicious cheeses, and beautiful landscapes, including miles upon miles of lakeshore coastline.

Check out these six Wisconsin destinations shared in more detail below.

• Madison, WI
• Milwaukee, WI
• Sheboygan, WI
• Door County, WI
• Wisconsin Dells, WI
• Lake Geneva, WI

Also, consider adding Green Bay (a 4-hour drive) and the lake-perfect Northwoods towns of Manitowish Waters and Boulder Junction (a 5.5-hour drive) to your driving trip wishlists.

Madison, Wisconsin

Approximate drive time from Chicago: 2.5 to 3 hours

Recommended by: Rebecca Gade Sawicki of VeggiesAbroad.com

At just two and a half hours from Chicago, Madison is the perfect destination for a quick day trip or a weekend away . This sustainability-focused college town offers families tons of outdoor activities, diverse dining, and art and culture.

If you’re a family that loves the outdoors, visiting Madison during the summer is best. This is the prime time to enjoy the city’s prized lake life (five lakes surround it) and over 200 miles of paved bike trails. Madisonians love to bike (even in the winter), which is one of the best ways to see the city.

Another great activity to see Madison’s unique and eco-friendly side is to explore the independent boutiques that line Willy Street. You’ll find plenty of vintage shops, locally created art, zero-waste products, and clothing that’s been ethically produced and sourced.

While you’re in the area, don’t miss an iconic Madison treat, Nutkrack — this sweet and salty snack was actually created by accident! And, around the corner from Nutkrack is Madison’s oldest vegetarian restaurant , Green Owl Café — don’t miss their loaded vegan cheese fries.

When deciding where to stay in the city, the best place is downtown. This will put you within easy walking distance of many shops, restaurants, and events.

The Hyatt Madison/Downtown offers spacious rooms and suites, perfect for families, along with continental breakfast, and has multiple sustainability initiatives to reduce its and its guest’s carbon footprint. Or search for more Madison lodging options here .

Sign up for my monthly Discovery Newsletter & get a free Trip Budget Calculator !

Milwaukee, Wisconsin

Approximate drive time from Chicago: 1.5 hours

Recommended by: Lisa of WavesandCobblestones.com

Milwaukee, Wisconsin , is the perfect city to visit on a family road trip from Chicago. Milwaukee is an easy 1.5-hour drive from Chicago, located to the north along the banks of Lake Michigan.

There are plenty of great things to do in Milwaukee to keep your family entertained! Rent kayaks and paddle along the Milwaukee Riverfront for some fresh air and exercise. Or show some team spirit and take the family to a ball game and watch the Brewers play baseball at the American Family Field or the Bucks on the basketball court at the Fiserv Forum.

There are many fun museums to visit in Milwaukee with your family, such as the Milwaukee Art Museum , a top-notch fine arts museum, where admission is free for children 12 years and younger. Or Discovery World , Milwaukee’s science museum, and Reiman Aquarium. Or the National Bobblehead Hall of Fame and Museum—a one-of-a-kind museum with over 10,000 bobbleheads from across the globe!

Stay at the Plaza Hotel , centrally located in Milwaukee’s historic Lower East Side, with suites that include a pull-out sofa and accommodate up to four people. The Plaza rooms have full kitchens, and with a large grocery store just a block away, you can save money on meals and snacks during your stay.

Or search for more Milwaukee lodging options here .

Sheboygan, Wisconsin

Approximate drive time from Chicago: 2.5 hours

Recommended by: Theresa Goodrich of TheLocalTourist.com

Sheboygan, Wisconsin, is a surprising destination only two and a half hours away from Chicago and a great road trip for families because of the variety of things to do. Begin your visit at the Visit Sheboygan Visitors Center and see Science on a Sphere , a suspended globe that acts as a projector screen displaying programs provided by the National Oceanic and Atmospheric Administration. You can also get tips for places to visit and pick up brochures and souvenirs.

One of the best things to do in Sheboygan for families is Bookworm Gardens. This whimsical garden is a haven for book lovers and children alike, where literature comes to life through vibrant displays and interactive exhibits. Another must-stop for families is the Above and Beyond Children’s Museum . You can’t miss it—there is a ship’s hull sticking out of the building! While downtown, stroll 8th Street for delicious pizza at Il Ritrovo , and don’t miss the Victorian Chocolate Shoppe . Since Sheboygan is on the shores of Lake Michigan, it is also a great summer vacation spot, with sandy beaches and lakefront parks .

Make Blue Harbor Resort your base camp. With its own waterpark, an arcade, mini-golf, a beach, and outdoor games—the kids will love staying at this resort. Or search for more Sheboygan lodging options here . 

Door County, Wisconsin

Approximate drive time from Chicago: 4 to 5 hours

Recommended by: Janice Moskoff of GatherandGoTravel.com

This Wisconsin peninsula just north of Green Bay, surrounded by Lake Michigan, boasts beautiful beaches, scenic hiking trails, and family-friendly activities that will keep everyone pleased for days. 

We visited Door County in the fall , and it was gorgeous. The leaves had not quite fully changed, though we took full advantage of the pretty outdoors to bike and hike at several of the peninsula’s five state parks . 

We even visited Cave Point County Park , one of the Door’s nearly 20 county parks, and were treated to an easy-to-access spectacular scene of Lake Michigan waves crashing against a stunning rocky coastline on a windy day. The beauty of this experience blew us away. Expect the Door to do the same to you.

In the summer, the Door truly shines. Families flock here for the beaches, events, and the abundance of outdoor activities. 

With over 300 miles of shoreline , you can swim, kayak, and fish in the crystal-clear waters of Lake Michigan, especially gorgeous on a sunny day.  Plus, the towns dotting the peninsula are charming, full of shops, galleries, and many restaurants.

Visit or stay on the west or bayside of the peninsula, where you can catch sunsets in towns like Fish Creek or Sister Bay . Or opt for the eastside—where we stayed—and catch the sunrises in or around Bailey’s Harbor . Top family-friendly resorts include Newport Resort , Ephraim Shores Resort , and Scandinavian Lodge . Though, know that the Door books early. So, if you plan your trip last minute, grab the best lodging you can get from Sturgeon Bay or further north and use it as a base to drive around and explore the Door. 

Search all family-friendly Door County lodging options on VRBO or Booking.com .

Wisconsin Dells, Wisconsin

Approx drive time from Chicago: 3 hours

Recommended by: Hannah & Adam Lukaszewicz of GettingStamped.com

The Wisconsin Dells is the ideal road trip destination from Chicago as it is known as the Waterpark Capital of the World . The driving distance from Chicago to Wisconsin Dells is just under three hours, making it the perfect length for a weekend getaway . Kids love to splash and play in the water, so why not visit multiple waterparks in one road trip?

The Wisconsin Dells is home to the first-ever indoor waterpark and currently has the largest concentration of waterparks in the world. No matter if you are visiting in the summer or the winter, you will find an amazing waterpark for your family to visit and enjoy, as the area is home to 12 different indoor water parks and over 20 water parks in total.

The best place to stay in Wisconsin Dells is one of the Waterpark Hotels . Our favorite waterpark hotel is Great Wolf Lodge as not only does it have a fantastic waterpark with a 6000 ft outdoor pool, 1000 gallon tipping bucket, a wave pool with three-foot-tall waves, a toddler pool, and a variety of slides for kids of all ages.

The Great Wolf Lodge has unique themed rooms and fun activities, including magi-quest, live shows, and an arcade, making it a kid paradise!

Lake Geneva, Wisconsin

Approximate drive time from Chicago: 2 hours

Recommended by: Diana of TravelsinPoland.com

With an approximate driving time of 2 hours, Lake Geneva is a short drive from Chicago and one of the best cities to visit in Wisconsin. The small-town atmosphere combined with a variety of activities make it a perfect choice for families with children of all ages.

Families can enjoy a day on the water, renting boats, kayaks, or paddle boards, or opt for a scenic boat tour around the lake. Or walk along a portion of the Lake Geneva Shore Path , a 21-mile trail that offers stunning views of grand estates and natural beauty. Spending time on the lake is the best way to experience the area, particularly during warmer months. Shopping in downtown Lake Geneva can keep families occupied for hours. The shops along the main roads have unique items such as art and handcrafted goods. There are also mom-and-pop cafes, ice cream, and candy shops in town.

For accommodation, The Abbey Resort , located in the heart of town, offers a great choice. It is a full-service family-friendly resort offering spacious rooms, indoor and outdoor pools, a game room for the kids, and a full-service spa for the adults. Or search for more Lake Geneva lodging options here .

Michigan & Ontario: Top Road Trips Within 5 Hours of Chicago

Experience the best of the Mitten State , a northern gem and a truly ideal destination for vacationing families. The Michigan coastlines—particularly to the west, with sandy beaches, spectacular sunsets, and towering dunes —will wow you with their beauty. Plus, the vibrant cities and small towns in Michigan will offer enough activities and culinary delights to keep you busy and satisfied for days.

Check out these four Michigan & Ontario destinations shared in more detail below.

• Saugatuck, MI
• Ann Arbor, MI
• Detroit, MI, into Ontario, Canada (a loop driving trip)
• Traverse City, MI (with a day trip to Sleeping Bear Dunes National Lakeshore)

To expand your options—consider adding these Michigan Southwest coastal towns to your road-trip-and-relax lists, like New Buffalo, St. Joseph/Benton Harbor, South Haven, Holland, and Grand Haven. Or spend time exploring more urban centers like Detroit or Grand Rapids .

Saugatuck, Michigan

Approximate drive time from Chicago: 3 hours

We love Saugatuck. We have visited for weekend trips several times in the fall and keep returning for more.  What draws us? The unbelievably beautiful beaches and dunes, the quaint downtown area filled with art galleries and boutiques, and the concentration of seriously elevated cuisine.

Our favorite beaches are Oval Beach , which consistently ranks as one of the top beaches in the country, and offers soft sand, clear water, and stunning views of Lake Michigan.  Additionally, we love the nearby and dog-friendly Saugatuck Dunes State Park , which is perfect for hiking and exploring, with over 1,000 acres of dunes, forests, and beaches.

When not visiting the beaches or getting ice cream, or shopping the galleries on Butler Street, Saugatuck’s main thoroughfare, we spend our time apple picking (in the fall), boating on the Kalamazoo River, or dining at one of the truly fantastic eateries in and around town. I share more things we love to do in Fall Trip: 10 Wonderful Family Things to Do in Saugatuck, MI “

Visiting families also love going on Saugatuck Dune Rides . This thrilling ride takes you on a tour of the dunes, with steep climbs and drops, which the kids will love. And bonus! The knowledgeable guides will share the history and ecology of the area, making it both fun and educational. 

For meals, you cannot go wrong nearly anywhere you choose to eat, but our favorites include The Southerner , where the biscuits alone are worth repeat visits, Pennyroyal Cafe & Provisions , and a short 15-minute drive to enjoy drinks and snacks at Virtue Cider .

Booking a stay in Saugatuck can be surprisingly pricey, so I share helpful information on where you can stay in the surrounding areas for less in “ Saugatuck, MI: 8 Amazing Areas to Search for Lodging .” Then, and especially because many local inns do not allow children as guests, I detail my top choices for family lodging in “ Roundup of the Best Family-Friendly Places to Stay in Saugatuck .”

Ann Arbor, Michigan

Approximate drive time from Chicago: 4 hours

Whether you’re a University of Michigan sports enthusiast or just looking for a hip town surrounded by gorgeous natural beauty, Ann Arbor is the ideal Michigan town to visit!  From Chicago, the trip via car or train (Amtrak offers service from Chicago’s Union Station to Ann Arbor) is just under four hours , making it a perfect road trip for a few days away!

Ann Arbor is well known for its thriving arts and culture scene . Year-round, it hosts a variety of art, music, and film festivals, including one of the largest outdoor art fairs in the nation, The Ann Arbor Art Fair . The Art Fair takes over Ann Arbor every July and spans 30 city blocks with over 1,000 artists! You’ll also find food and music throughout the fair.

For families who enjoy outdoor activities, you’re in luck! Ann Arbor is surrounded by natural beauty, with parks, nature reserves, and the Huron River flowing through it. Head to the Argo Livery during the summer and rent a canoe, kayak, or stand-up paddle board. You can go out on your own, or Argo offers multiple group river trips that range in time and distance from just under 4 miles and 1.5 hours to almost 6 miles and 2.5 hours.

When it comes to dining, you’re in for a treat — the city is well-known for its eclectic mix of cafes and restaurants. From the famous and funky sandwiches at Zingerman’s Delicatessen to the veggie eats at Ann Arbor’s best vegan restaurant, Detroit Street Filling Station.

When choosing a place to stay, it’s best to stay right in the heart of the city (especially if it’s your first visit). Two terrific family options include the Residence Inn by Marriott Ann Arbor Downtown and The Graduate Ann Arbor . Or search for more Ann Arbor lodging options here .

Detroit to Southwestern Ontario Loop Trip (a 5 Day, 4 Night Itinerary)

Approximate drive time from Chicago to Detroit: 4.5 hours

Recommended by: Erie Conners of EverywhereOntario.com

For a unique road trip that takes you into another country, consider making the trip from Chicago to Southwestern Ontario , Canada.  This southernmost region of Canada is filled with quaint small towns, sandy beaches , an abundance of fruit farms and wineries , and incredible historic sites that tell important stories from the Underground Railroad that delivered many slaves to freedom in the 1800s. 

From Chicago, you’ll drive 4 hours to the Detroit-Windsor border. In Detroit, you’ll cross the Ambassador Bridge or take the Detroit-Windsor Tunnel to get into Canada. 

Depending on how long you’ll be staying in Canada, here are the sites I recommend according to a path that takes you from the Detroit-Windsor border to the Sarnia-Port Huron border , where you’ll loop back to Chicago:

• Optional overnight at Caesar’s Windsor Hotel , or search for other Windsor lodging .
• Or, Pelee Island : Take the ferry to Canada’s southernmost landmass, Pelee Island. Visit Pelee Island Winery and bike around the island before taking the ferry home. Overnight in Leamington at a beautiful B&B , or other lodging . 
• Grand Bend Beach : Visit one of Ontario’s top beaches in the summer months. Lounge on the beach, participate in water sports, or walk along the Grand Bend Strip for boutique shopping.
• Sarnia: Walk along the waterfront to see Port Huron from the Canadian side. Overnight at The Insignia Hotel , in Sarnia . Or stay search for other nearby lodging .
• Cross the Bluewater Bridge back to Port Huron and drive 5 hours back to Chicago.

Traverse City, Michigan

Approximate drive time from Chicago: 5 to 5.5 hours

We visited vibrant Traverse City, MI , picturesquely nestled at the southern u-shaped end of Grand Traverse Bay , for five days in the heart of summer with our family dog and loved every minute of our trip. 

In addition to enjoying the lakeshore views that front the length of the town and strolling the shops and restaurants of bustling Front Street, our favorite activities were biking along the wooded TART trails—especially the Leelanau Trail, and hiking. 

We walked the paths in Grand Traverse Commons Natural Area , located behind the outdoor shopping plaza, making our way to the Hippie Tree, a massive old willow tree at the center of the trail network. Painted in bright colors by locals representing living artwork, the tree is rumored to have a haunted history that we only learned about after our visit. 

On another day, we drove out to the Old Mission Point Peninsula to spend the day enjoying the sweeping lake views from the lighthouse, hiking the trails in the adjacent Old Mision Point Park , stopping to buy fresh farmstand cherries, picking blueberries with the kids, and to enjoy a late al fresco lakeside lunch at the Jolly Pumpkin Restaurant & Brewery .

Another highlight was taking a day to visit the Sleeping Dunes National Lakeshore (a 40-minute drive), where we climbed dunes, hiked the Empire Bluff Trail , one of many in the area , and relaxed and picnicked on dog-friendly Esch beach. 

In addition to the outdoor activities, which could also include boat trips on Lake Michigan or kayaking on local lakes or rivers, your family will love the varied collection of breweries and wineries with outdoor dining areas ideal for families. When visiting, you can stay at a centrally located and family-friendly hotel, like the Bayshore Resort . Or search for a rental in the area. Find more available Traverse City hotels and lodging here . 

Indiana: Top Road Trips Within 5-Hours of Chicago

Hang out in the Hoosier State in one of these two top destinations:

• Indiana Dunes National Park, IN
• Indianapolis, IN

Additionally, consider staying in French Lick, IN, at the French Lick Resort  (a 5-hour drive), located in the hills of Indiana’s Hoosier National Forest. It is a classic family-friendly Americana resort offering loads of activities including, golf, biking, hiking, spa treatments, and supervised drop-off kid activities.

Indiana Dunes National Park, Indiana

Approximate drive time from Chicago: 45 minutes

Recommended by: Caitlin Dismore of TwinFamilyTravels.com

If you are in the Chicago area and looking for a family-friendly trip nearby, definitely consider visiting Indiana Dunes National Park and the surrounding area. Just 45 minutes outside of the city, the park offers a beautiful setting with plenty of beach access points and hiking trails.

In addition to the fabulous activities within the park, the surrounding towns offer a variety of attractions, shopping, and dining to keep the whole family entertained. West Beach is the perfect place for a family outing. It’s the largest beach in Indiana Dunes National Park and is great for swimming, sunbathing, or just relaxing. The Lake Michigan water is clean and clear, and there’s plenty of sand for kids to play with.

Hiking is another popular activity while in the park. Explore Indiana Dune’s biodiversity by hiking along the boardwalks, past historic homes, and even through marsh areas. If you are up for it, complete the 3 Dune Challenge at the nearby Indiana Dunes State Park .

If you are traveling with young children, consider staying at the Country Inn & Suites By Carlson Portage . The hotel has both a standard indoor pool and a shallow pool specifically designed for children, complete with a frog slide. Or search for other lodging options in the nearby Portage, Indiana area.

Indianapolis, Indiana

Approximate drive time from Chicago: 3 to 3.5 hours

This lively Midwestern city offers a wide range of activities and attractions ideal for families. From world-class museums to racetracks , expect a visit to Indy will be a memory-making trip your kids will love.

Top spots include the Indianapolis Children’s Museum , which has 472,900 square feet and five halls of exhibit space, making it the largest children’s museum in the world!  While there, kids can explore science, history, and art exhibits. Or they can ride a carousel, board a train, or climb a giant treehouse.

Prefer outdoor activities?  Be sure to visit the Indianapolis Zoo and White River Gardens , where the kids can roam, see amazing things, and do fun activities. In addition to seeing tigers, dolphins, and orangutans, the kids can visit the petting zoo, ride trains, join for animal feedings, or watch cheetah racing. 

For families who love cars and racing, include a visit to the Indianapolis Motor Speedway . Known as the “Racing Capital of the World,” the speedway is home to the famous Indianapolis 500 race and offers tours of the track and museum. When in the area, stop for burgers and root beers at the Mug ‘n Bun, a nearby vintage drive-in.

On where to stay, consider booking a room at the five-star Conrad Indianapolis tops the list with its spacious rooms and prime downtown location. Prefer something less splurgy? The more budget-friendly Homewood Suites by Hilton Downtown Indianapolis , with a complimentary breakfast, makes for an excellent alternative. Or search for other lodging options in the Indy area here .

Illinois: Top Road Trips Within 5-Hours of Chicago

Check out these top locations in the Land of Lincoln: 

• Starved Rock State Park, IL
• Shawnee National Forest, IL

Also, consider a visit to Galena (a 2.5 to 3-hour drive) with a historic downtown full of shops and restaurants, nearby outdoor activities like walking and biking along the Galena River, and lots of family-friendly lodging , some with pools.

Starved Rock State Park, Illinois

Recommended by: Alyssa of AnAppleaPlane.com

Only 1.5 hours by car outside the bustling city of Chicago, Starved Rock State Park transports visitors into another world. Dramatic canyons and cascading waterfalls are not the first things you picture when you think of the Midwest!  

If you do not plan to drive your own car, renting one will be most effective for your time and budget. Or, you can get to the area by taking a train from Chicago’s Union Station to Mendota Amtrak Station and hailing a 30-minute cab to the park. A huge draw to Starved Rock is its easy-to-access features . Many of Starved Rock’s most famous waterfalls provide drive-up parking lots, so the walk to the waterfall is only a couple of minutes.

Alternatively, consider parking at the main visitor center lot and hiking to your waterfalls of choice. Waterfalls at Starved Rock flow after rainfall or snow melt, so be mindful that these will not be here year-round. The longest-lasting waterfalls are at St. Louis Canyon and La Salle Canyon.

Other top features of the park include hiking, boat tours, and camping . And perhaps the park’s biggest draw—the entrance is free !

Consider staying in the highly-rated Starved Rock Lodge for either cabin or hotel room options. Or search for other nearby family-friendly lodging options here .

Shawnee National Forest, Illinois

Approximate drive time from Chicago: 5 hours

Recommended by: Melissa of HelloWanderlustFamily.com

Located in southern Illinois, Shawnee National Forest is about a 5-hour drive from Chicago, making it an easy and accessible destination for families. 

One of the best things about Shawnee National Forest is its variety of activities , such as hiking, fishing, ziplining, or just relaxing in nature—it offers something for everyone.  Two must-see attractions are Cave in Rock and Little Grand Canyon Trail. Cave in Rock is a 55-foot-wide cave formed over thousands of years by the forces of the Ohio River and the wind, and a highlight of Little Grand Canyon Trail is you get to hike in and around a series of waterfalls that cascade down the rocky cliffs. 

When looking for a place to stay, consider the location of your planned activities . Shawnee National Forest is huge, with some attractions only 15 minutes away, while others may take an hour to reach. Because of this, choose accommodation closer to the area where most of your activities will be. One excellent lodging option for families is Home2 Suites in Carbondale , which not only provides larger room sizes and access to a pool but is in a city that offers plenty of amenities. Or search for more Carbondale lodging options here . Alternatively, for a more unique and memorable experience, consider staying at the Timber Ridge Outpost & Cabins , which offers cozy treehouses perfect for families seeking a one-of-a-kind stay.

Gurnee, Illinois

Approximate drive time from Chicago: 45 minutes to 1 hour

Recommended by: Lisa of PlanningAway.com

If you are looking for a fun short road trip from Chicago, Gurnee Illinois is just the place! There are lots of fun things to do in Gurnee, Illinois !  Gurnee is about 45 minutes north of the city. Home to Six Flags Great America and Great Wolf Lodge , it is the perfect place to spend a fun weekend.   

Six Flags Great America is the highlight of a trip to Gurnee. There are over 30 roller coasters and rides to explore. There is also a water park inside Six Flags called Hurricane Harbor. Six Flags has great shows and entertainment options for all ages.  

To relax after a fun day at Six Flags, stay nearby at Great Wolf Lodge , where you can enjoy many activities, including an indoor water park, Magiquest game, rock climbing, ropes course, arcade, bowling, and mini golf.  Kids will also love character meet and greets, dance parties, and many other fun activities by Great Wolf Lodge, and included in your stay. The lodge is perfect for kids under the age of 12 . 

There are some places to eat inside Great Wolf Lodge, but if you want to really experience Gurnee, you will want to venture out and try some local favorites. Kaiser Pizza is delicious, and Oberweis Ice Cream is a must. Gurnee Mills shopping and outlet mall is a good stop for families too. Shop at the Bass Pro, eat at the Rainforest Cafe, and enjoy many more fun shopping options. If you do not want to stay overnight—Gurnee also makes for a great day trip from Chicago.

Missouri: Top Road Trips Within 5-Hours of Chicago

Saint louis, missouri.

Approximate drive time from Chicago: 4 hours 30 minutes

Recommended by: Lynli Roman of Wanderbig.com

With less than five hours between cities, Saint Louis is a family getaway that feels far away but is easy to drive from Chicago in a half-day! Book a room at the railroad depot turned hotel , Union Station , and spend your time exploring the many family-focused activities that Saint Louis offers.  First, take your family to explore the City Museum . Described as “weirdly wonderful,” the City Museum is the crown jewel of family-friendly fun in St Louis. Housed in an old shoe factory, the City Museum boasts a huge network of slides, tunnels, and caves for all ages. All ages love the rooftop, where you can ride the Ferris wheel or climb a giant praying mantis for perfect views of the St Louis skyline. 

Next, wander through Soulard Farmers Market and taste your way through the city. The Soulard Farmers Market is one of the oldest markets in the United States, with roots dating back to 1779! Most alive during the weekends, you’ll find 147 stalls filled with unique vendors selling everything from local Missouri produce to handmade gifts. Nearby grounds include a playground and plenty of space for an impromptu picnic with your market spoils. 

No family road trip to St Louis is complete without a trip to Forest Park— one of the nation’s largest and most-visited urban parks. The park is home to the Saint Louis Art Museum , the Saint Louis Science Center , the Missouri History Museum , an outdoor theater, and the Saint Louis Zoo . Entrance fees vary, but many amenities, including general admission to the zoo, are free!

Want to see more St. Louis lodging options ? Search for other family-friendly accommodation options here .

Ohio: Top Road Trips Within 5-Hours of Chicago

From city trips to world-class amusement parks to under-the-radar natural gems, Ohio regularly delights visitors , and especially families, with all it offers as a vacation destination.

Four Buckeye State destinations to consider for your next road trip include:

• Cincinnati, OH
• Cleveland, OH
• Cuyahoga Valley National Park, OH
• Cedar Point Amusement Park, OH

Cincinnati, Ohio

Approximate drive time from Chicago: 4.5 to 4.75 hours

Recommended by: Linda of MidwestExplored.com

If you’re looking for one of the best family road trips near Chicago—you can’t beat Cincinnati, Ohio.  After all, this underrated city is located just four and a half hours, or 297 miles, away from Chicago and is a well-priced, family-friendly destination brimming over with fun Cincinnati things to do that everyone will love.

So, start your visit with a trip to The Cincinnati Art Museum , founded in 1881, and in the Eden Park area.  Not only is the museum free to visit, but there are over 67,000 works that cover 6,000 years, ensuring there is something for everyone at this incredible institution. 

Next, grab a picnic lunch and explore Ault Park , which spans an impressive 220 acres of land and is the city’s fourth-largest park, and features a wealth of picnic areas, playgrounds, and walking trails that will help keep energetic kids busy. Finally, learn more about the Underground Railroad at the National Underground Railroad Freedom Center before taking in the electric hue of the cool signs on display at the American Sign Museum.

Then, when you’re ready to call it a day, return to your room at the Hyatt Regency Cincinnati , where you can take advantage of their family-friendly suites, indoor pool and catch up on laundry at their on-site facility. Or search for more Cincinnati lodging options here .

Cleveland, Ohio

A visit to Cleveland truly offers the best of all worlds—thrills at nearby Cedar Point Amusement Park (1-hour drive), cultural chills, and hills made for hiking at Cuyahoga Valley National Park (30-minute drive).  Stay in town at a place like centrally located and highly-rated Roost Cleveland , which offers fully furnished apartments with hotel-like perks,  and use it as a base to explore the area. 

The city, on the shores of Lake Erie, is home to the Rock and Roll Hall of Fame, the Cleveland Museum of Art, and the Cleveland Orchestra—great destinations and cultural institutions for families to experience and explore.  And when your crew gets hungry, head to the historic West Side Market to grab a bite from local food vendors and souvenir shop for artisanal products.

For families with outdoor enthusiasts, pair a visit to Cleveland with a day trip to Cuyahoga Valley National Park , a 30-minute drive away, where you can hike one of many highly rated wooded or waterfall trails.

Want to see more Cleveland lodging options ? Search for other family-friendly accommodation options here .

Cuyahoga Valley National Park, Ohio

Another must-see destination for families visiting Ohio is Cuyahoga Valley National Park .  Located just outside Cleveland (a 30-minute drive), this park offers over 33,000 acres of natural beauty and outdoor activities. 

Families can explore the park’s hiking trails , go fishing or kayaking on the Cuyahoga River, or even take a scenic train ride.  With its pretty waterfalls, wooded paths, and diverse wildlife, Cuyahoga Valley National Park is a perfect destination for families looking to get outside, get moving, and enjoy the best of what nature and national parks offer.  

If you do not plan on staying in Cleveland, consider booking rental lodging in tiny and historic Peninsula Village , a private island of town surrounded by Cuyahoga Valley National Park.  Top rental picks in Peninsula, OH, for families include a few three and four-bedroom homes that can sleep up to ten. Search “Peninsula, OH” on VRBO  to find them.

Cedar Point Amusement Park, Ohio

Approximate drive time from Chicago: 4.5 hours

Cedar Point Amusement Park , located on a peninsula extending into Lake Erie near Sandusky, Ohio, is surrounded by water and overflowing with family-style fun. 

Known as the “ Roller Coaster Capital of the World ” with over 70 rides, including 18 roller coasters—thrill-seeking families will love it. The park also features a water park, live entertainment, and plenty of family-friendly dining.  Take at least two days to enjoy all it has to offer.

Stay on-site at one of the Cedar Point resorts like the beachfront Hotel Breakers , Lighthouse Point offering cottages and campgrounds, Castaway Bay with an indoor water park, or the budget-friendly Cedar Points Express Hotel .

Kentucky: Top Road Trips Within 5-Hours of Chicago

Louisville, ky.

Need a reason to visit Louisville, KY? How about six? Your family will love visiting the Louisville Zoo or strolling along Waterfront Park facing the Ohio River and adjacent to downtown Louisville, stopping to play in playgrounds or cool down in hot summers at the splash park. 

While in the area, catch a ride on a riverboat like the Belle of Louisville , which offers several different types of cruises, including historic narrated ones to picnic lunch cruises . Or your whole crew might love the Hometown Music Kids Cruise , designed especially for families.

Kids and parents who love baseball—or love to see how things how are made—will enjoy a visit to the Louisville Slugger Museum & Factory , conveniently located downtown. Your tickets give you access to the museum and a tour of the factory—kids even get a free mini-bat at the end of the tour.

Need an indoor day activity? Explore the Mega Cavern , a former limestone quarry, now an underground adventure park offering ziplining, ropes courses, and a bike park, just a 15-minute drive from downtown and near the Zoo.  Or visit the downtown Kentucky Science Center , where your kids can engage with exhibits about the human body and outer space.

For places to stay, The Grady Hotel and Homewood Suites by Hilton Louisville Downtown are great choices. Both hotels are centrally located downtown and highly rated. Or search for more Louisville lodging options here . 

Related Reading

For traveling families, check out my related articles below for more trip ideas and tips that will help smooth your travels and get out the door with less hassle.

• Need An Itinerary For A Spring Trip To Europe? Here Are 25 Amazing Ideas
• 31 Warm Winter Break Vacation Ideas Your Family Will Love
• Enjoy the Ride: 12 Tips for Better Family Road Trips
• 15 Tips on How to Raise the Bar on Rental Cars
• Pack Faster & Better With This Universal Printable Packing List
• 25 Expert Packing Tips to Help You Travel Better
• Pre-Trip: A Practical Checklist to Close the House & Pack

Additional Trip Planning Resources

To further help you with travel planning, I share my go-to resources for every trip below. 

Google Flights. My first research stop for affordable flights for every trip. Learn why here . 

Google Hotels . Use its “ Where to stay ” button to discover the best neighborhoods to base your visit.

Booking.com. For hotel and rental bookings, I appreciate its flexible cancellation, candid user reviews, discounts, loyalty program, and easy-to-use interface.

Viator , Get Your Guide , & Airbnb Experiences . Quickly find and book highly-rated tours and activities on these sites.

Google Travel Things to Do & Google Maps . Find more things to do in your destination on Google Travel, then record where you want to visit on a custom Google Maps list. 

AllTrails . Love to hike? Me too. I religiously use AllTrails to discover hiking and biking trails and download its offline maps to manage my hikes.

Guide Along . 5-star self-guided audio tours that are GPS-compatible for US road trips and national parks. We loved the Glacier National Park tour .

Insure My Trip. I never travel internationally without trip insurance. Learn why here . My preferred place to shop and compare policies is InsureMyTrip.com . 

Plus, check out the 15 travel apps I use on trips, my preferred guidebooks , and my free customizable travel itinerary template , downloadable in four file formats.

About the author:  Janice Moskoff is a travel writer and blogger who loves hiking, exploring the world, and reading. She writes to inspire travel-loving families, adult friends, and couples on her blog,  Gather and Go Travel . Check out  her bio , learn how she became  a blogger , and discover how to  work with her . Sign up for her monthly  Discovery Newsletter  to get her latest travel recommendations and  how-to’s .

Love to travel? Sign up for m y monthly Gather & Go Travel Discovery Newsletter and get a free trip budget calculator .

Affiliate Disclosure: Some of the links on this page may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I only recommend products and companies I use. And the income goes to keeping the site community-supported and ads minimal.

From An Expert: InsureMyTrip.com is My #1 Pick for Trip Insurance

35 Places You Will Love for Your Next Ladies’ Trip

How to Make the Most of Missoula in 3 Days

39 Amazing Ideas for Things to See & Do in Missoula

The Best Places to Eat Around Glacier National Park

The Best Places to Stay Near Glacier National Park

Leave a reply.

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

Welcome to Gather and Go Travel , a blog inspiring families, adult friends, and couples to explore US and international destinations and to get outdoors. I am Janice, an experienced traveler to over 50 countries and a travel writer, book lover, and blogger. Learn more about me , read our story , and how to work with me .

Need an Itinerary for a Spring Trip to Europe? Here are 25 Amazing Ideas

49 Things You Need to Do to Plan Your Best Trip (Free Travel Research & Planning Checklist)

Rental Car Insurance: When You Need It & When You Don’t

Pack Faster & Better With This Universal Printable Packing List

How to Spend 10 Days In Rome, the Amalfi Coast & Sorrento

Instagram....

gatherandgotravel

📍US & 🌎 travel for families, friends + couples 📝 Itineraries, destination guides and ideas + tips ❤️ hiking🥾, mountains + 📚books 🏡 Chicago

love this info?

And receive our F REE Budget Trip Calculator .

© 2023 All Rights Reserved

Travel planning.

Amazeballs Better Travel Guide

Travel Planning Tips

Destinations

Travel Learning

Conversations With Travel Pros

Blogs I Love To Follow

Work With Me / Contact Me

Journey From 100 To 10K

Terms of Use

Privacy Policy

Get A Free Trip Budget Calculator

Sign up for my monthly gather & go travel discovery newsletter packed with tips and vacation ideas and get my trip budget calculator for free..

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

6 Best Road Trips From Chicago

Waterfalls, storybook towns, incredible food, and more await just a short drive from Chicago.

Cities can sometimes feel like endless stretches of concrete — especially in the hot summer months — and Chicago is no exception.

Fortunately, there's a whole world out there beyond the city limits. While it doesn't always feel like it, there are so, so, so many worthy escapes within a few hours' drive of Chi-town: storybook towns studded with ice cream parlors, lakeside cities with entirely different cultures, and even places where you can connect with nature among waterfalls and lush trees. Waterfalls! Outside Chicago!

The Windy City's location, in this case, is your ally. Pack your car with some picnic accoutrements, and maybe some hiking gear just in case, and head off. You're within driving distance of some truly great, out-of-the-ordinary places that make for wonderful road trips. Here are six of them.

Madison, Wisconsin

Imagine a state already known for its beer and cheese having to cater to over 30,000 college students, and you've got some idea of the earthly delights that await in Madison, Wisconsin. This state capital could have been a destination in its own right for its unique geography — located on a narrow isthmus surrounded by two large lakes, it's beautiful even during cold Wisconsin winters — or its remarkable breadth of shopping, cultural events, and festivals, and architecture, but its food scene is virtually unrivaled for a city of its size.

The streets are filled with an eclectic mix of professors, politicians, businesspeople, street performers, and health nuts, and if you ask any of them for their favorite spot, you'll likely get a range of answers as large as the city's 250,000-plus population: American small bites at the new and renowned Mint Mark, tacos and margaritas at Canteen, Lao-Thai noodles from Vientiane Palace, and the list goes on and on.

Most students, however, will drive you toward craft-beer watering holes like The Malt House or Dotty Dumpling's Dowry, which purportedly serves one of the best burgers anywhere. Wash it down with some Wisconsin beer from New Glarus as well as some fried cheese curds, and you'll have yourself a real Madison, Wisconsin, night.

Madison is about two and a half hours from Chicago.

Starved Rock State Park, Illinois

Yes, Illinois isn't known for its natural beauty like some other states. Yes, its highest natural point is Charles Mound, a diminutive 1,235-foot hill. But that doesn't mean that hidden gems don't exist here. For a true escape from Chicago's steel-and-stone skyscrapers that is still within the state limits, drive to the area around Starved Rock State Park.

Visitors expecting more flat Illinois farmland will be surprised to find an incredible valley around the Illinois River, with lush trees, striking bluffs, and 14 gorgeous waterfalls feeding into the roaring waters. Starved Rock is a choice destination for camping, hiking, kayaking, and white-water rafting, and after you're exhausted from a day of physical exertion, it's also got a place to hang your hat: the Starved Rock Lodge .

However, if you feel like experiencing a bit more of the local flavor, the towns around the river valley provide it in buckets. Tiny, charming Utica is home to the August Hill Winery and some wonderful antique stores, while the historic towns of Oglesby and Ottawa are chock-full of Americana: small museums, galleries, and great food, particularly at the Red Dog Grill in Ottawa and The Rootbeer Stand in Oglesby.

Starved Rock State Park is about an hour and a half from Chicago.

Allegan County, Michigan

Lake Michigan is huge. And in the summertime, when the heat gets a little unbearable, you could easily just jump into the lake in Chicago. But there's something to be said for taking a jaunt out to Michigan to visit a string of lakeside towns that bring some truly unique qualities to the mix.

Douglas, Saugatuck, and Holland — and Fennville, though it's not right on the water — epitomize small-town charm, while still offering some truly city-sized amenities for city-sized appetites. Fennville is known as the fruit basket of Michigan, with apple orchards, vineyards, and berry farms alongside delightful creameries and even corn mazes, while Saugatuck and Douglas consistently take the cake as two of the best lakeside towns in the Midwest, with incredibly charming downtown areas, gorgeous undulating sand dunes, pristine blue water, and more art galleries than you can shake a stick at. In fact, it's here that two School of the Art Institute of Chicago instructors founded their own art school and residence, Ox-Bow, establishing an artists' colony right on the shores of Lake Michigan. Their legacy endures to this day.

Further up the road, you'll find a truly unique destination in Holland, where Dutch colonists established a foothold in the 1800s, bringing with them their culture, architecture, pastries (check out DeBoer Bakkerij), and even fields' worth of tulips, which you can find at Veldheer Tulip Gardens.

Fennville is about two hours from Chicago.

Indianapolis, Indiana

Among the many types of travelers out there — people who crave solitude, people who don't want to leave the 100-foot radius of their resort's pool — there are those who are fascinated by city life, jumping from one urban area to another. If you count yourself among them, a road trip from Chicago to Indianapolis is certainly warranted.

First off, it's the 15th-largest city in America, with a vast population and penchant for festivals, parties, and overall pageantry (it is the Racing Capital of the World, after all, and its famous month of May includes tons of smaller celebrations leading up to the Indy 500). No matter the time of year, though, you'll find Indianapolis in full swing, whether you're in the midst of its rollicking IndyFringe Festival in August and September or its Wine & Food Festival in June. It's also a museum hub, with the world's largest children's museum, several art museums with broad and granular focuses, and small museums focusing on its favorite children, from Vonnegut to President Benjamin Harrison.

But one of the main reasons visitors flock to Indianapolis is its incredible food scene, which has, in recent years, exploded into national prominence. Hot new restaurants like Bluebeard, Milktooth, Crispy Bird, Oca, and more have all contributed to its reputation as a gastronomical powerhouse, while iconic institutions like Workingman's Friend have been, well, working behind the scenes to keep Hoosiers well-fed for decades. It's about time their city gets noticed.

Indianapolis is about three hours from Chicago.

Traverse City, Michigan

If you're craving a real getaway, you can't do much better than northern Michigan — it's still within driving distance of Chicago and not as remote as the state's Upper Peninsula, while still providing a wilderness-tinged escape for city dwellers. The de-facto capital of the region, Traverse City, is a city in name, but its population of around 15,000 means it's got small-town charm and accessibility, making it a perfect gateway to the region's breathtaking sights. Stop in for a glass of beer or wine at one of the many famous wineries and brewpubs, like Mari Vineyards or Mackinaw Brewing Company, before heading into the wilderness.

From Traverse City's quaint streets, you can head north and explore the Leelanau Peninsula, or veer west to Sleeping Bear Dunes National Lakeshore. Better yet, take scenic M-22 to tick off both boxes. Sleeping Bear Dunes is one of the country's best stretches of shoreline, with incredible dunes and westerly views that mean it's got some of the best sunsets east of the Mississippi.

From there, mosey up M-22 to continue exploring the Leelanau Peninsula, where wilderness encroaches a bit further and small towns, each with a population under 1,000, dot the roads. Hike through the dense forests, pick apples and berries at the region's many farms, and be sure to grab a heaping sandwich from the Village Cheese Shanty in the county seat of Leland (population 377).

Traverse City is about five hours from Chicago.

Galena, Illinois

In rare cases, a road trip doesn't just mean traveling great distances — it can also mean traveling back in time. That's what's figuratively the case when you drive west from Chicago to Galena, consistently rated as one of the best small towns in America. For decades, Galena has been on a mission to preserve its rich history, meaning it has one of the most unspoiled historic town centers in the country.

The town's good fortune started back in the mid-1800s, when it was the beneficiary of government grants to begin mining precious minerals located under the town. Since then, the town has focused on maintaining the buildings from that boom time, and there are architectural landmarks around every corner. The Galena Historic District is a particular delight, comprising more than 1,000 buildings, including the home of Ulysses S. Grant, a prime example of the Italianate style and now a dedicated memorial to his legacy. The town even has trolley tours that take you to its major historical and architectural benchmarks, contributing to its overall throwback feel.

Galena's best eating institutions don't necessarily date all the way back to 1850, but that doesn't mean they aren't also great — Durty Gurt's Burger Joynt was founded in 2007 and serves gigantic, almost architecturally impressive stacks of meat and cheese. Looks like everyone's concerned with building a legacy here.

Galena is about three hours from Chicago.

Related Articles

North America Chevron

United States Chevron

Illinois Chevron

Chicago Chevron

Best Weekend Getaways From Chicago

By Nina Kokotas Hahn

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

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

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

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

LAKE FOREST, ILLINOIS

Distance from Chicago 33 miles

The Deer Path Inn

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

Where to Stay

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

INDIANA DUNES NATIONAL PARK, IN

Distance from Chicago 49 miles

The dunes overlooking Lake Michigan at Indiana Dunes National Park

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

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

HARBOR COUNTRY, MI

Distance from Chicago 75 miles

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

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

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

KOHLER, WISCONSIN

Distance from Chicago 149 miles

Shana Clarke

Lane Nieset

Paris Wilson

One of the Kohler luxury Cabins

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

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

Distance from Chicago 164 miles

Downtown Galena

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

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

INDIANAPOLIS, IN

Distance from Chicago 185 miles

The Bottleworks Hotel in Indianapolis' Bottleworks District

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

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

BOYNE, MICHIGAN

Distance from Chicago 346 miles

A look down Boyne Mountain

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

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

Recommended

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

• Jun 21, 2022

26 Best Weekend Getaways from Chicago (within a 4-hour flight)

Updated: Jan 21

Deep dish pizza, sports, great bars, and awesome summers. Chicago has it all (except the ocean and nice winters). If you're looking to take a break from the norm in Chicago or escape the brutal winter, read on for some ideas about where to go for a quick weekend.

With a vast array of short domestic destinations, there are also many international destinations within reach. Here are some weekend getaway ideas for locals in the Chicago area within a non-stop 4-hour flight. More importantly, these trips are all possible without having to request PTO (for you M-F 9-5'ers), it just depends on what you want to do at your destination.

Miami, Florida (MIA, FLL) - Just Over a 3 Hour Flight

Beaches, outdoors activities, clubs, restaurants, culture. I just ask that you please please please venture out beyond Miami Beach.

When to go?

Any time of the year, but best is October - February for perfect weather. Avoid the spring break crowd in late Feb/early March the best you can.

Who can fly you there?

AA from ORD - See flight deals

Spirit Airways from ORD - See flight deals

Southwest from ORD, MDW - See flight deals

United from ORD - See flight deals

How much will it cost to get there?

Airfare: $100+

Where can you stay?

See hotels in Miami

See hotels in Miami Beach

Visit the following neighborhoods to step away from the "typical Miami": Wynwood, Brickell, Coral Gables, Coconut Grove, Midtown, Edgewater.

Orlando, Florida (MCO) - Just Under a 3 Hour Flight

Disney & Universal Studios. Bring bug spray and an umbrella if you go during the summer.

Frontier from ORD - See flight deals

Airfare: $150+

See hotels in Orlando

New York, New York (JFK, LGA, EWR, ISP, HPN) - 2 Hour Flight

It might not be the same city it was a few years ago, but it'll always make for a great weekend getaway.

Summer for the best weather, but peak rates for solid hotels.

Winter for Christmas festivities!

Delta from ORD - See flight deals

JetBlue from ORD - See flight deals

Airfare: $50+

See hotels in New York

Toronto, Ontario (YYZ, YTZ) - Just Under a 2 Hour Flight

Food, people, cleanliness, Hockey Hall of Fame.

Air Canada from ORD - See flight deals

WestJet from ORD - See flight deals

Swoop from ORD - See flight deals

Porter Airlines from MDW - See flight deals

See hotels in Toronto

Philadelphia, Pennsylvania (PHL) - 2 Hour Flight

History, sports, cheesesteaks

Summer and Fall

United Airlines from ORD - See flight deals

Airfare: $200+

See hotels in Philadelphia

Washington, DC (IAD, DCA, BWI) - Just Under a 2 Hour Flight

Museums, walking tours, great mass-transit and cherry blossoms. Fly to DCA for convenience.

Year-round (spring season for cherry blossoms)

See hotels in Washington DC

For avid runners, pack your running shoes and go for daily runs around the White House, Washington Monument, Lincoln and Jefferson memorials.

Discover the ease of weekend escapes from Chicago with ING Chauffeured Transportation , your trusted choice for dependable ground transportation.

Kansas City, Missouri (MCI) - 1.5 Hour Flight

BBQ! BBQ! BBQ!

Southwest from MDW - See flight deals

See hotels in Kansas City

Visit the Power & Light District for a unique nightlife experience & go to Arthur Bryant's for BBQ.

Nashville, Tennessee (BNA) - 1.5 Hour Flight

Music (not just country), endless bars, brewpubs, hot chicken.

Spring, Summer and Fall

See hotels in Nashville

Stay in the Gulch or near printer's alley.

New Orleans, Louisiana (MSY) - 2.5 Hour Flight

Jazz music, other music, culture, architecture, partying, passionate football fans.

Spring, Summer, Fall

See hotels in New Orleans

Check out Bourbon Street for a little bit, but don't get sucked in. It's absolutely disgusting. Chartres Street is better for those looking to maintain their cleanliness.

Atlanta, Georgia (ATL) - 2 Hour Flight

Brew pubs, art, nightlife, Mexican food.

Delta from ORD, MDW - See flight deals

Frontier from MDW - See flight deals

See hotels in Atlanta

Walk some of the BeltLine and stop at stores, bars, and restaurants.

Raleigh, North Carolina (RDU) - 2 Hour Flight

Outdoors activities, restaurants, college sports, booming tech sector.

See hotels in Raleigh

Glacier National Park, Montana (FCA) - Just Over a 4 Hour Flight

Glacier National Park and the great town of Whitefish. I recommend camping, but you can get a boutique hotel in Whitefish or Kalispell.

SkyWest from ORD - See flight deals

Airfare: $350+

See hotels in Whitefish

Austin, Texas (AUS) - Just Under a 3 Hour Flight

Food, Art, Music, BBQ, Tech, Bach Parties, and All-Around Fun!

See hotels in Austin

Cancun, Mexico (CUN) - Just Under a 4 Hour Flight

Your money goes a long way: all-inclusive hotels, nightlife, and activities.

December to April for the best weather.

Avoid March Spring Break travel if you want to be at peace.

See hotels in Cancun

Jackson Hole, Wyoming (JAC) - Just Over a 3 Hour Flight

Bears, Yellowstone National Park, Grand Teton National Park, skiing, golfing, horseback riding, rustic boutique hotels, cool people.

Airfare: $400+

See hotels in Jackson Hole

Make sure you have time to visit both Yellowstone and Grand Teton. Jenny Lake is a must.

Aspen, Colorado (ASE) - Just Over a 3 Hour Flight

Skiing, great scenery, luxury.

See hotels in Aspen

It's very expensive, but worth a shot. 3.5 hour drive if you wish to save some $$.

Boston, Massachusetts (BOS) - Just Over a 2 Hour Flight

History and cool summertime temps!

Intercontinental Boston

See hotels in Boston

Las Vegas, Nevada (LAS) - 4 Hour Flight

Gambling, Hoover Dam, Death Valley National Park, Valley of Fire State Park, Partying, more Gambling.

See hotels in Las Vegas

Denver, Colorado (DEN) - Just Under a 3 Hour Flight

Mountains, beer, National Parks, hiking, clean city, nice people.

Year-round. Ski in the winter. Hike in the summer.

Airfare: $250+

See hotels in Denver

Salt Lake City, Utah (SLC) - 3.5 Hour Flight

Skiing, Salt Flats, Mormons, and great National Parks within a moderate drive.

See hotels in Salt Lake City

Nassau, Bahamas (NAS) - 3.5 Hour Flight

Turquoise waters, friendly people, and close proximity to Florida make the Bahamas a popular destination.

December to July to avoid hurricanes and tropical storms.

May to August to avoid crowds and surcharges.

November to February to avoid the summer heat.

Airfare: $500+

See hotels in Nassau

Rent a car ! Be prepared to drive on the left side of the road.

Charleston, South Carolina (CHS) - 2 Hour Flight

History, culture, family-friendly attractions, and watersports.

See hotels in Charleston

Asheville, North Carolina (AVL) - Just Under a 2 Hour Flight

Art, craft beer, and the Smoky Mountains. I'd recommend driving instead of flying, but it's your call!

Allegiant from MDW - See flight deals

See hotels in Asheville

Montreal, Quebec (YUL) - 2 Hour Flight

More restaurants per capita than any other North American city.

See hotels in Montreal

Bozeman, Montana (BZN) - 3.5 Hour Flight

Skiing, Hiking, Waterfalls, Museums, Rivers, and of course Yellowstone National Park (1.5-hour drive). It's possible to do the park in one day from Bozeman, but if going to the park is your goal, I'd recommend staying closer to the park in West Yellowstone.

See hotels in Bozeman

See hotels in West Yellowstone

Rapid City, South Dakota (RAP) - 2.5 Hour Flight

You'll find nature and parks galore in one of the most unique areas of the country. Mt. Rushmore National Monument, Custer State Park, Black Hills National Forest -- all within a 35 min drive from Rapid City, in the same direction. Do all 3 in one day and be sure to visit Sylvan Lake in Custer. Just incredible. Badlands National Park is 1 hour away and that's doable in a separate day. Devils Tower National Monument is just under 2 hours in the opposite direction across the Wyoming border.

See hotels in Rapid City

• Tips and Advice
• North America

Recent Posts

3 Best Weekend Getaways from Bakersfield, California (within a 4-hour flight)

7 Best Weekend Getaways from Fresno, California (within a 4-hour flight)

6 Best Weekend Getaways from Sacramento, California (within a 4-hour flight)

Hey! I'm Jordan, a native New Yorker who is addicted to adventure travel, photography, content creation, investing, and fitness. Read on, enjoy, and Never Run Out of First Times!

23 Best Weekend Getaways from Washington DC (within a 4-hour flight)

15 Best Weekend Getaways from Las Vegas (within a 4-hour flight)

Best Things to Do in Hudson Valley for a Memorable Night Out

10 Fairy-tale Wedding Locations in California: From Castles to Enchanted Forests

18 Best Weekend Getaways from San Antonio (within a 4-hour flight)

23 Best Weekend Getaways from Austin (within a 4-hour flight)

5 Best Places to Fly a Drone in Miami

5 Buildings Shaping Miami's New Skyline

A Snob’s Guide to Chicago

Is this list exhaustive? Maybe not. But it is highly opinionated, and that’s all that really matters.

I started visiting Chicago regularly after college, when my closest friends moved there. We went to the old Bistro 110 and felt very proud when we graduated to drinks at the Violet Hour and the Aviary, and then dinner at the Publican and Girl & the Goat (still favorites). There are things on this list I’ve loved for 30 years. Others became musts more recently. I also get a little help from my highly opinionated friends and family. Let’s call them the HOFs.

1. Check into the recently refreshed and perfectly located Park Hyatt Chicago. Ask for a lakeside room (on an upper floor). The Lake Michigan and Park Suites feel as if you are actually on the water.

2. “Walker Bros. for breakfast!” HOF and Chicago native Brooke Garber Neidich advises. “49ers pancakes, very crispy bacon, fresh-squeezed OJ.”

3. Take an architecture cruise. I like the Chicago Architecture Center River Cruise. I do this every time.

4. Have lunch at RL. Before Polo Bar in New York, before Ralph’s in Paris, there was RL in Chicago. It’s the OG.

5. Check into the Peninsula Chicago. Also right there on the Magnificent Mile. Have afternoon tea in the lobby and dumplings at the Shanghai Terrace. In winter ask about the skating rink!

6. The Langham (and its big, gorgeous rooms) is also a favorite.

7. Walk along Michigan Avenue to the Art Institute. (On the way, take your Kapoor Bean selfie.) The Thorne Miniature Rooms are a must, as is the Seurat that inspired Sondheim and Grant Wood’s American Gothic . The museum website has a great “what to see in an hour” guide.

8. ”The Field Museum of Natural History is also fabulous,” interjects HOF William Li. “The Hall of Jades! Go.”

9. “And the Fairy Castle at the Museum of Science and Industry!” Brooke says.

10. Riverwalk? Yes, says HOF Kate Chappell, news anchor for NBC Chicago. “End with sunset views at Tiny Tapp.”

11. Do the Frank Lloyd Wright Home and Studio tour in Oak Park. Ice cream at Petersen’s (around since 1919) afterward.

12. “Go see Robie House,” says my HOF niece and Chicago undergrad, Cayla, of Wright’s landmark. Reservations required. Afterward “get a Mediterranean omelet ­cafeteria-style at Valois, and try to sit at President Obama’s table, or have excellent Southern-inspired food at Roux.”

13. See a show at the Goodman Theatre. The hot ticket for 2024 will be Taylor Mac and Rob Ashford’s Midnight in the Garden of Good and Evi l (June 25–August­ 4).

14. And at the Steppenwolf. Laurie Metcalf will star in an as yet untitled show. It doesn’t get more Chicago than that.

15. And anything at the Lyric Opera.

16. “ The chorizo-stuffed bacon-wrapped ­medjool dates at Avec,” I say.

17. “A steak and a martini at Gene & Georgetti!” Brooke says.

18. “The tuna crudo and stracciatella appetizer at Rose Mary,” Cayla says. (I second this, and also a walk around the Fulton Market District.)

19. “The Hong Kong–style roast meats at Sun Wah BBQ,” William says.

20. “ The chicken pot pie, truffle bucatini, and the burger at Armitage Ale House,” Cayla says.

21. “Pasta at Monteverde. Any of them,” says basically everyone you will ever talk to.

22. “The thin crust pizza at Nancy’s in West Loop,” Kate says. That’s all I’ll say on the pizza matter.

23. The Kalamata chicken at the Athenian Room. It’s how Chicago theater royalty Carrie Coon and Tracie Letts celebrate their anniversary. (If that doesn’t matter to you, the rest of this list might not either.)

24. Wait in line for the Au Cheval burger. It’s a rite of passage. Same goes for dinner at Alinea. I have never been, and am ashamed.

25. Go to a Garrett Popcorn shop before you leave. Get tubs of the cheddar-and-caramel. Bring me some.

Editor-in-Chief Stellene Volandes is a jewelry expert, and the author of Jeweler: Masters and Mavericks of Modern Design (Rizzoli).

@media(min-width: 40.625rem){.css-1jdielu:before{margin:0.625rem 0.625rem 0;width:3.5rem;-webkit-filter:invert(17%) sepia(72%) saturate(710%) hue-rotate(181deg) brightness(97%) contrast(97%);filter:invert(17%) sepia(72%) saturate(710%) hue-rotate(181deg) brightness(97%) contrast(97%);height:1.5rem;content:'';display:inline-block;-webkit-transform:scale(-1, 1);-moz-transform:scale(-1, 1);-ms-transform:scale(-1, 1);transform:scale(-1, 1);background-repeat:no-repeat;}.loaded .css-1jdielu:before{background-image:url(/_assets/design-tokens/townandcountrymag/static/images/diamond-header-design-element.80fb60e.svg);}}@media(min-width: 64rem){.css-1jdielu:before{margin:0 0.625rem 0.25rem;}} In the Magazine @media(min-width: 40.625rem){.css-128xfoy:before{margin:0.625rem 0.625rem 0;width:3.5rem;-webkit-filter:invert(17%) sepia(72%) saturate(710%) hue-rotate(181deg) brightness(97%) contrast(97%);filter:invert(17%) sepia(72%) saturate(710%) hue-rotate(181deg) brightness(97%) contrast(97%);height:1.5rem;content:'';display:inline-block;background-repeat:no-repeat;}.loaded .css-128xfoy:before{background-image:url(/_assets/design-tokens/townandcountrymag/static/images/diamond-header-design-element.80fb60e.svg);}}@media(min-width: 64rem){.css-128xfoy:before{margin:0 0.625rem 0.25rem;}}

Meet Broadway's Newest Stars

This Is What Happens When a Jewelry Icon Evolves

Roman and Williams Celebrates T&C's April Issue

Anatomy of a Classic: Il Bisonte's Consuelo Bag

The T&C Investment Portfolio: Home Edition

Why Billionaires Are Buying Up Sports Teams

Sanderson Launches New Home Collection

Did Marie Antoinette Have the Best Bed in Europe?

The Dawn of the Dumb House

Investment Portfolio April 2024: Wedding Edition

Zoe Otedola & Cole Weston's Bucolic Wedding

Block Club Chicago

Your Neighborhood News Site

25 Things To Do In Chicago This Weekend: Cinco De Mayo, Spring Markets, Critical Mass And More

Share this:

• Click to share on Facebook (Opens in new window)
• Click to share on Reddit (Opens in new window)
• Click to share on Twitter (Opens in new window)
• Click to share on WhatsApp (Opens in new window)
• Click to email a link to a friend (Opens in new window)

Credibility:

• Original Reporting
• Sources Cited

CHICAGO — April showers bring May flowers, and plenty of spring festivities around the city.

Kick off the month with Cinco de Mayo celebrations, tours through Pilsen and Little Village with Chicago historian Shermann “Dilla” Thomas, a Critical Mass bike ride through the South Side, a pop-up makers market and more.

There’s also a Kentucky Derby party at an Irish pub, a new theatrical adaptation of “Bluey” on stage at the Auditorium Theatre, a massive record sale and Chicago Humanities Festival events.

Here’s a roundup of 25 things to do in Chicago this weekend:

West Town First Friday

5-8 p.m. Friday

West Town Chamber of Commerce, 1819 W. Chicago Ave., and other venues

The West Town Chamber of Commerce has partnered with Intuit: The Center for Intuitive and Outsider Art for a new exhibit opening Friday evening. In conjunction with West Town First Friday, a time when local art galleries stay open late, the month-long exhibit will kick off with a family-friendly opening at 1819 W. Chicago Ave.

Neighbors can also visit participating art venues that will be open until 8 p.m., such as Vertical Gallery, Fulton Street Collective, The Chicago Fine Art Salon, ARC Gallery, Mariane Ibrahim Gallery and more. Find more information here .

Southside Critical Mass Chicago Bike Ride

5:45-10 p.m. Friday

Start at the south end of Nichols Park, 1300 E. 55th St.

Join fellow Chicagoans and cyclists for a monthly social bike ride through the South Side, which takes places on the first Friday of each month April-November. The group normally travels at a moderate pace of 15-20 miles per hour. Participation is free, but all riders are responsible for their own bikes, masks, helmets, water, bike locks, bike lights and other gear.

The goal of Critical Mass is to uplift cycling as a method of transportation in Chicago and “to make our neighborhoods more bikeable and … liveable.” Learn more here .

‘Bluey’s Big Play’

6 p.m. Friday; 11 a.m., 2 p.m. and 5 p.m. Saturday; 2 p.m. Sunday

Auditorium Theatre, 50 E. Ida B. Wells Drive

Chicagoans can step into the world of Australian heeler dog Bluey through “Bluey’s Big Play,” a new theatrical adaptation of the International Emmy-winning children’s show. The play features an original story by “Bluey” creator Joe Brumm, new music by “Bluey” composer Joff Bush and puppetry.

Buy regular and resale tickets through Ticketmaster . Learn more about the production here .

LEGO & Libations

7 p.m. Friday

KOVAL Distillery, 4241 N. Ravenswood Ave.

Neighbors are invited to enjoy cocktails and build their own LEGO set at KOVAL Distillery Friday evening. The goal is to “learn how to think like a designer.” All LEGO materials will be provided.

Tickets are $15-20 online .

Sound Meditation At The Zoo

9 a.m. Saturday

Lincoln Park Zoo, 2001 N. Clark St.

Led by facilitator Jay Taylor, Chicagoans can wind down with an hour-long sound meditation at the Lincoln Park Zoo’s wildlife center. Surrounded by the sounds of singing bowls, guests will be guided through light breathing exercises, meditation and reflection.

Tickets are $40 online .

View this post on Instagram A post shared by Marché Privé Chicago (@marcheprivechicago)

Marché Privé

10 a.m.-3 p.m. Saturday

The Promontory, 5311 S. Lake Park Ave.

Marché Privé is a new luxury pop-up market and daytime social for Chicago entrepreneurs who are Black, Indigenous or people of color. It’s hosting its inaugural themed showcase this weekend in honor of Derby Day, featuring more than 15 local vendors, a bar and music by a DJ. Attendees are encouraged to wear derby-inspired attire.

Learn more and RSVP online .

Old Town School Of Folk Music Record Sale

10 a.m.-5 p.m. Saturday and Sunday

Music Direct, 1811 W. Bryn Mawr Ave.

The Old Town School of Folk Music is collaborating with Music Direct for a two-day record sale featuring thousands of donated LPs, rare 78s, books, CDs, DVDs, records and equipment. Saturday also features a live performance by Steve Dawson and Diane Christiansen of Dolly Varden from 1-3 p.m.

Each purchase will help support the Old Town School of Folk Music’s resource center and its library of books and recordings. Learn more here .

Cosmic Cinco de Mayo

Various times Saturday

Chitiva Wicker Park Bucktown, 1948 W. North Ave., and Chitiva South Loop, 1250 S. Michigan Ave.

Enjoy games, music and themed drinks in honor of Cinco de Mayo at Chitiva locations in Wicker Park and South Loop. There will be games, music, tacos, “cosmic margarita” slushies and other plant-infused mocktails.

Wicker Park festivities are 11 a.m. Saturday through 1 a.m., and South Loop festivities are 3-11 p.m. Saturday.

Derby Day Party

11 a.m. Saturday

River Shannon, 425 W. Armitage Ave.

Watch the Kentucky Derby while enjoying drinks, hat contests and giveaways. Learn more here .

Dear Mama Pop-Up Shop

11 a.m.-4 p.m. Saturday

Mt. Pisgah Social Hall, 4622 S. King Drive

This early Mother’s Day pop-up shop features local vendors and a variety of food by 40+ Double Dutch sister Del, who will be serving jerk eggrolls, jerk tacos, salads and more. Guests are invited to bring their own jump ropes and try out hula hooping.

Learn more here .

Spring Market For Makers

11 a.m.-5 p.m. Saturday and Sunday

Artifact Events, 4325 N. Ravenswood Ave.

Shop more than 120 artisans and small businesses at this family-friendly market. There will also be food, drinks, photo opportunities and complimentary tote bags for ticket holders. Kids 12 and under get in free, and pets are welcome.

Learn more and buy tickets for $8-15 online .

Cinco De Mayo Tours With Dilla

1-3 p.m. Saturday and 2-4 p.m. Sunday

Chicago Women’s Park & Garden, 1801 S. Indiana Ave.

Celebrate Cinco de Mayo with a two-hour bus tour of Pilsen and Little Village, two of Chicago’s oldest neighborhoods, led by Chicago historian Shermann “Dilla” Thomas. Dilla will cover their histories dating to the 1800s, from the “Bohemian Czechs who laid out the streets … to the burgeoning Mexican communities of today.” Sites include Benito Juarez High School, the 16th Street murals, the Mexican Museum of Modern Art and Thalia Hall.

Tickets are $48 online .

Dog Days Adoption Event

1-5 p.m. Saturday

Sidetrack The Video Bar, 3349 N. Halsted St.

Enjoy drinks while meeting adoptable dogs and pets at this event by Alive Rescue. There will be dog swag and treats for “canine customers.” Attendees must be 21 and older with a valid ID to enter.

View this post on Instagram A post shared by Chicago Humanities (@chihumanities)

Dr. Todd Boyd: Hip Hop History From The Notorious Ph.D.

2-3 p.m. Saturday

Ramova Theatre, 3520 S. Halsted St.

Dr. Todd Boyd, a professor and author who has studied race and popular culture in America, will be delving into hip-hop’s history, legacy and influence on American life with Chicago artist Open Mike Eagle. The two will delve into the genre’s highs, lows, past and present in a Chicago Humanities Festival presentation, followed by a book signing with Boyd.

Learn more and buy tickets for $15-25 online .

View this post on Instagram A post shared by Logan Center for the Arts (@loganuchicago)

May Family Saturday At The Logan Center For The Arts

2-4 p.m. Saturday

Logan Center for the Arts, 915 E. 60th St.

This month’s Family Saturday at the Logan Center for the Arts follows a “Marine World” theme and features a variety of family-friendly activities. There will be arts and crafts with Live Arts Studio, creative movement with Kenwood School of Ballet, puppetry with Nitzana Lazarus and more.

Learn more and find the schedule here .

Celebrate Her: Women In The Arts

4 p.m. Saturday

Ka’Lab Bronzeville, 501 1/2 E. 47th St.

This interactive pop-up is celebrating women in the arts with music and dance performances — from poetry to rap, jazz to folk, dance to group song to drag artist — plus presentations by local women-owned businesses.

Learn more and buy tickets for $15 online . Drinks, light appetizers and tacos will be available for purchase.

Golden Hour: A Drum & Bass Dance Party

5-8 p.m. Saturday

Epiphany Center for the Arts, 201 S. Ashland Ave.

Golden Hour is a jungle dance party with live music and food and drink specials. This weekend features live sets from artist collective Drum & Bass Identity, or DnBid .

Admission is free. Learn more and RSVP here .

Ronnie Malley: A Musical Reflection

7 p.m. Saturday

Co-Prosperity, 3219 S. Morgan St.

Chicago native and Palestinian musician Ronnie Malley will perform an original new work, “On This Earth,” for the Chicago Humanities Festival this weekend. An expert oud player, Malley uses his Middle Eastern lute to bridge his American and Palestinian identities. His upcoming repertoire features sacred and secular Andalusian music, Middle Eastern music and Palestinian folk songs.

Teen Open Mic

Armitage Concert Hall, 909 W. Armitage Ave.

This monthly open mic with the Old Town School of Folk Music offers a space for teenagers to perform and share their talents with one another.

Learn more and buy tickets for $3 online .

View this post on Instagram A post shared by Elim Chan (@itselimchan)

‘Sheherazade’

7:30 p.m. Saturday

Chicago Symphony Orchestra, 220 S. Michigan Ave.

Acclaimed Hong Kong-born conductor Elim Chan leads the Chicago Symphony Orchestra this weekend through “Sheherazade,” a musical suite based on the Middle Eastern folktales of “One Thousand and One Nights.”

Tickets start at $49 online .

Star Wars Night With Chicago Fire FC

Soldier Field, 1410 S. Museum Campus Drive

“May the 4th be with you” as Chicago Fire FC takes on New England Revolution this weekend. To honor the Star Wars-themed occasion, the first 5,000 fans will get a limited edition of Chicago Fire FC flag featuring Yoga. There will also be various themed activations and surprises revealed as the game approaches.

Learn more and buy tickets and resale tickets here .

Read & Run Chicago: ‘Becoming’

9-11:30 a.m. Sunday

Boxville, 330 E. 51st St.

Take an easy-paced 5.5-mile jog through Bronzeville and Hyde Park with Read & Run Chicago, a local running book club. The group will lead runners through the neighborhoods, stopping at locations that shaped Michelle Obama’s life as a South Shore student and Loop lawyer, as outlined in her book “Becoming.” After the tour, attendees can head back to Boxville for a raffle, coffee, bites and books.

Learn more and sign up for $0-10 online .

Mother’s Day Native Art Market

10 a.m.-4 p.m. Sunday

American Indian Center, 3401 W. Ainslie St.

Ahead of Mother’s Day, the American Indian Center is hosting a market with Native artisans, Indian tacos and fry bread, plus Native dance and drum performances starting at noon. Attendees can find gifts for mother figures in their lives while immersing themselves in Native culture.

View this post on Instagram A post shared by The Promontory – Music Venue (@promontorychicago)

Taco Fest: Cinco De Mayo

2-8 p.m. Sunday

In celebration of Cinco de Mayo, Hyde Park music and events space The Promontory will have DJs spinning reggaeton, Afrobeat, hip hop, R&B and other tunes all day. There will also be five taco vendors serving up Mexican cuisine, cocktails, live body painters and more.

Tickets are $20-35 online .

Outcast Jazz Band’s Big Band Dance Party

5 p.m. Sunday

Chicagoans can enjoy a night of music and dance with Outcast Jazz Band, an 18-piece group that’s been swinging their way through Chicagoland ballrooms and events for over 40 years. This weekend’s party will offer swing dance lessons and pay homage to the classic big band sounds of Count Basie, Duke Ellington, Glenn Miller and more.

Tickets are $20 online and $25 at the door.

Support Local News!

Subscribe to Block Club Chicago , an independent, 501(c)(3), journalist-run newsroom. Every dime we make funds reporting from Chicago’s neighborhoods. Already subscribe?  Click here to gift a subscription , or you can support Block Club with a tax-deductible donation.

Listen to the Block Club Chicago podcast:

9 Unforgettable Family-Friendly Things to Do in Chicago

W hen seeking family fun in the Windy City, Chicago’s abundant attractions and vibrant culture offer an array of unforgettable experiences. From iconic parks to historic landmarks, the city invites families to embark on exciting adventures that cater to all ages. Discover the top family-friendly things to do in Chicago with your loved ones and create cherished memories that will last a lifetime.

1. Millennium Park: Modern Marvels and Outdoor Delights

A visit to Millennium Park promises a seamless blend of modern marvels and natural beauty, captivating visitors of all ages. Marvel at the enigmatic “Bean” sculpture that reflects the city’s skyline, explore cutting-edge modern art exhibits, and enjoy leisurely strolls in the family-friendly park. With an outdoor performance venue that hosts diverse events, Millennium Park provides an enchanting setting for creating lasting memories against the backdrop of Chicago’s skyline.

But that’s not all—Millennium Park’s Crown Fountain beckons families to cool off in summer as the interactive digital faces spout refreshing water, adding laughter to the air. Also, don’t miss the Jay Pritzker Pavilion, an architectural marvel hosting concerts and performances, where you can unwind while enjoying music and the city’s artistic spirit.

2. Engage in Sports Fever: Embrace Chicago’s Athletic Spirit

Immerse your family in Chicago’s passionate sports culture by attending live games featuring iconic teams like the Bears, Cubs, White Sox, Bulls, and Blackhawks. Be it football, baseball, basketball, ice hockey, or soccer with the Chicago Fire, the city’s fervor for sports is palpable. Experience the electric energy of the crowd and witness top-notch athleticism, giving your family a taste of the Windy City’s competitive spirit.

Additionally, the Chicago Sports Museum within Water Tower Place offers an interactive experience that lets you test your skills against Chicago legends, making sports history come alive. Explore memorabilia, engage in virtual games, and learn about the city’s sports legacy in an engaging and educational environment.

3. Stroll the Pedestrian Paradise: Downtown Delights

Downtown Chicago beckons families to explore its vibrant streets, where storefront attractions and pedestrian-friendly destinations invite leisurely walks. Along the scenic Lake Shore Drive, iconic stops like Navy Pier and the captivating Shedd Aquarium await. For shopping enthusiasts, the renowned Magnificent Mile on Michigan Avenue and State Street boasts a captivating blend of classic and contemporary shopping experiences, satisfying diverse tastes.

Moreover, Navy Pier’s Centennial Wheel takes family fun to new heights, offering sweeping views of Lake Michigan and the city skyline. Afterward, immerse yourselves in the interactive exhibits of the Chicago Children’s Museum , where creativity and learning converge for kids of all ages.

4. Immerse in Art and Entertainment: Theatrical Treats

Discover Chicago’s vibrant arts scene by treating your family to an array of performances and cultural explorations. From acclaimed Broadway shows like Wicked to ballet and orchestral concerts, the city’s theaters cater to all tastes. Delight in comedy at the famed Second City, where Saturday Night Live cast members launched their careers. Explore the city’s rich artistic landscape, including the captivating Lyric Opera.

Furthermore, Chicago’s Museum Campus features the Adler Planetarium, where families can embark on cosmic adventures through immersive shows and exhibits. Explore the mysteries of the universe and spark your family’s interest in science and space exploration.

5. Savor the Waterfront Experience: Navy Pier Adventures

Navy Pier, a historic freighter hub turned family-friendly attraction, promises a trove of adventures for visitors of all ages. Gaze in awe at the Ferris wheel towering 150 feet above, and indulge in onsite amusements like an 18-hole miniature golf course and musical carousel. Cultural gems like the Chicago Shakespeare Theatre provide captivating performances against the backdrop of Lake Michigan, creating a unique family experience.

For a touch of nostalgia, explore the Chicago Children’s Museum within Navy Pier, a haven for interactive learning and play. Engage your kids’ curiosity with exhibits that cover topics from art and science to engineering, all designed to make learning an exciting adventure.

6. Touch the Sky: Sears Tower Skydeck

Elevate your family adventure to new heights at the Sears Tower Skydeck, offering one of the most breathtaking views of Chicago’s skyline. Gaze out over up to 50 miles on clear days, marveling at the sprawling cityscape that extends to parts of Michigan, Indiana, and Wisconsin. Ascend together to the sky and share the awe-inspiring panorama from this iconic Chicago landmark.

As you stand on the Skydeck, don’t forget to step onto The Ledge—a glass balcony extending from the tower’s exterior. This exhilarating experience allows you to see the city beneath your feet, creating an unforgettable memory of conquering new heights together.

7. Dive into Marine Wonders: Shedd Aquarium Exploration

Shedd’s Aquarium right at the top of the best family-friendly things to do in Chicago . Embark on a captivating aquatic journey at the Shedd Aquarium, where marine life from around the world awaits discovery. While children marvel at the displays, adults find equal delight in the exotic species like piranhas, anacondas, and vibrant coral reefs. The aquarium offers an immersive experience that allows your family to explore the diverse ecosystems that thrive in our planet’s oceans and waterways.

For a deeper understanding of aquatic conservation, participate in Shedd’s educational programs that promote marine stewardship. Engage in interactive workshops, encounter marine animals up close, and leave with a renewed commitment to protecting our oceans.

8. Shop and Explore: The Magnificent Mile Experience

The renowned Magnificent Mile along Michigan Avenue is a shopper’s paradise, offering a mix of upscale department stores, luxury boutiques, and renowned hotels. Indulge in retail therapy at establishments like Gucci, Coach, Chanel, and Tiffany & Co., all while enjoying the charming cityscape. Explore this fashion-forward district and create lasting memories amidst Chicago’s retail wonderland.

To make your shopping experience even more memorable, consider visiting during the Magnificent Mile Lights Festival, where holiday lights illuminate the street, and festive activities like a tree-lighting parade and fireworks create a joyful family atmosphere.

9. Discover Cultural Gems: Chinatown’s Charms

Venture into the vibrant world of Chicago’s Chinatown, where a rich tapestry of shops, eateries, and cultural events awaits. Uncover the enchanting sights of parades, festivals, and unique celebrations that offer a glimpse into the heart of this cultural haven. From souvenirs to authentic cuisine, Chinatown invites your family to embrace its dynamic atmosphere and indulge in a world of sensory delights.

As you explore Chinatown, be sure to visit the Chinatown Square, where you’ll find a captivating fusion of traditional and modern architecture. Discover hidden gems like herbal shops, tea houses, and bakeries, offering an immersive experience that’s as educational as it is delightful.

Family Family-Friendly Things to Do in Chicago: Explore Chicago’s Treasures

As you explore family-friendly things to do in Chicago, you’ll unearth a treasure trove of experiences that cater to every age and interest. From modern wonders to historic landmarks, this dynamic city opens its arms to families seeking unforgettable adventures. Embrace the city’s diverse culture, rich history, and vibrant attractions as you embark on a journey of discovery, creating memories that will linger in your hearts for years to come.

Let’s Be Besties!

Signup for our occasional news and special offers – oh, and gifts! I send out gifts often!

You have successfully joined our subscriber list.

Awesome, you're subscribed!

Thanks for subscribing! Look out for your first newsletter in your inbox soon!

The best of Chicago for free.

Sign up for our email to enjoy Chicago without spending a thing (as well as some options when you’re feeling flush).

Déjà vu! We already have this email. Try another?

By entering your email address you agree to our Terms of Use and Privacy Policy and consent to receive emails from Time Out about news, events, offers and partner promotions.

Love the mag?

Our newsletter hand-delivers the best bits to your inbox. Sign up to unlock our digital magazines and also receive the latest news, events, offers and partner promotions.

• Things to Do
• Food & Drink
• Time Out Market
• Coca-Cola Foodmarks
• Attractions
• Los Angeles

Get us in your inbox

🙌 Awesome, you're subscribed!

The best weekend getaways from Chicago for families

Take a break from the city and find family-friendly activities throughout the Midwest on these weekend getaways.

Chicago boasts plenty of kid-friendly activities  and restaurants , but if you're planning a family vacation, there are many approachable, fun and memorable destinations close by for a weekend away. Cities, state parks and lakes across the region are full of hiking for all ages and engaging, hands-on ways to learn about history, ecology and wildlife. Along the way, discover quirky shops, longstanding eateries with decadent desserts and recreational activities that kids of all ages will enjoy. From wacky and weird to active and relaxing, here are the best  weekend getaways from Chicago for families.

RECOMMENDED:  The best day trips from Chicago  RECOMMENDED:   The most unique day trips from Chicago

An email you’ll actually love

Family weekend getaways from Chicago

1.  Wisconsin Dells, WI

Driving time from Chicago: Three hours The waterpark capital of the world—what's not to love? It doesn't matter if the weather is sunny or rainy, though, because this Wisconsin town offers both indoor and outdoor parks. Mt. Olympus is one of the biggest and most popular, with both water and theme park attractions (and rides for the really little ones as well). Those looking to do something a little different can visit MagiQuest in the Great Wolf Lodge to participate in a live-action role-playing game. If the little ones come up for air long enough to eat, head to Buffalo Phil's , where kids get their food delivered on a train before spending some coinage in a giant arcade. Paul Bunyan's is a fun, themed spot for an all-you-can-eat breakfast.

If you're looking for animals, look no farther than Timbavati Wildlife Park for behind-the-scenes tours with exotic animals. Or let the kids feed gentle deer at Wisconsin Deer Park .

2.  Hamilton County, IN

Driving time from Chicago: Three hours Take a trip back in time at the Conner Prairie Interactive History Park  and explore 1836 Prairietown, see a Civil War reenactment or stroll along the nature walk. There’s also a large Swiss Family Robinson–esque tree house called Treetop Outpost for the whole family to enjoy. Then, of course, there's Conner Prairie’s tethered helium balloon, which elevates guests 377 feet above the prairie for unbeatable views over Indiana.

Nearby, you can take to the more than 300 miles of trails in the county, including paved paths that lead to shopping, dining and sightseeing. Bring your bike or rent one during your stay.

3.  Lake Geneva, WI

Driving time from Chicago: One and a half hours At a sprawling resort like the Grand Geneva , you can count on plenty of activities to keep the family busy. Explore the Dan Patch Stables , where the kids can go on pony rides and feed the animals in the free petting zoo. Waterpark lovers will clamor for Moose Mountain Falls , a 50,000-square-foot waterpark. For dinner, check out Popeye's (not the chain with an amazing fried chicken sandwich): It's super family-friendly with great views of the water and a large menu.

4.  Door County, WI

Driving time from Chicago: Four hours

A longtime favorite of Chicagoans seeking a bit of R&R, Door County has more to do than your family will be able to fit into just one weekend. Kids will make some amazing memories with the host of experiential activities, like feeding a baby goat at The Farm ,  making their own crafts at Hands On  or ziplining, gem mining or go-karting at Egg Harbor Fun Park . More active families will love exploring the stunning Cave Point County Park --you can even get kayak cave tours or stand-up paddleboards through Gravity Trails . 

The region isn't short on kid-friendly restaurants either -- go for highly cutomizable wood-fired pizzas at Wild Tomato or watch goats graze on the roof at Al Johnson's Swedish Restaurant and Butik . And don't forget to stop at Door County Creamery for some indulgent gelato. 

5.  Indianapolis, IN

Driving time from Chicago: Three hours Indianapolis has enough indoor and outdoor activities for a fun-filled weekend. Head to  The Children's Museum of Indianapolis  for top-notch exhibits like the planetarium and the Dinosphere, where kids can dig for dinosaur bones. It also has a great play area for toddlers. For some fresh air, walk or bike along the Monon Trail, a 10.5-mile path that runs through most of Indy. Stop in the Broad Ripple neighborhood to browse some shops and grab a scoop of ice cream at Brics .

Rest your weary heads at the Crowne Plaza Downtown Indianapolis Union Station , and be sure to call ahead to check for family packages that may include lodging plus tickets to attractions like the Children's Museum and  Indianapolis Zoo .

6.  Holland, MI

Driving time from Chicago: Two and a half hours Since the mid-19th century, the small city of Holland has been home to wooden shoes and tulips. Whether you're there in time for the Tulip Time Festival in May or want to visit the Windmill Island Gardens , the family will have a blast. Check out a working 250-year-old Dutch windmill—”De Zwaan,”—or stroll 36 acres of pristine lawns; bring your picnic blanket and a camera for a vibrant family photo op. During the day, catch a tour of the 125-foot windmill from a guide in traditional plaid Dutch garb. Need even more flowers? See more than 5 million in bloom in April and May at Veldheer Tulip Gardens . To take home a piece of Holland, though, you must not miss De Klomp Wooden Shoe and Delft Factory , where you can also enjoy a free tour of the famous, centuries-old pottery maker from the Netherlands. Once you've worked up an appetite, take the kids out for an authentic Dutch dessert like sugar bread from deBoer Bakkerij . If you need to burn off some energy, a 20-minute drive takes you to Saugatuck Dunes State Park . Surrounded by 300 acres of nature and dunes that rise up to more than 200 feet tall, you won’t have a care in the world running and playing along this long, sandy shore.

7.  St. Louis, MO

Diving time from Chicago:  Five hours

Brimming with attractions, St. Louis is perfect for families. The iconic Gateway Arch is an absolute must—you’ll understand why when you reach the top of the 630-foot-tall monument—but don’t miss the interactive, immersive City Museum , an educational playground with slides, sculptures you can play on and even vintage pinball machines. If nature’s your thing, the Missouri Botanical Garden has one of the largest Japanese gardens in North America, the Saint Louis Zoo is free and home to more than 600 species of animals and the St. Louis Aquarium features a 250,000-gallon shark habitat.

8.  Peoria, IL

Driving time from Chicago: Two and a half hours

There’s plenty of family-friendly history, recreation and adventure in Illinois’s oldest European settlement. Enjoy the scenic views and watch the barges go by along the RiverFront District before making a stop at the The Peoria Riverfront Museum to immerse yourself in space shuttle launches, solar systems and eclipses in the domed planetarium. Then fill up on smoked meats and burgers at The Blue Duck Barbecue Tavern , housed in a repurposed train depot utilized from 1899 to 1978. Sleep close to the activities at the Mark Twain Hotel , a quaint and understated 111-room accommodation 10 minutes walking from the RiverFront.

You’ll also find lots of greenery and wildlife to experience, even within city limits. Spend time at the 60 square miles of parks—the oldest park district in Illinois. Wander around the 5-acre Luthy Botanical Garden for year-round floral beauty or hike through seven miles of trails in Forest Park .

9.  Harbor Country, MI

Driving time from Chicago: One hour and 15 minutes With a population of less than 2,000 permanent residents, the small lakefront city of New Buffalo is charming for all ages. If traveling by train, Amtrak will drop you off near The Harbor Grand , where a stay feels like home but cozier, with an in-room fireplace and harbor view (or glimpse of a frozen lake). During warm months, you can hop on one of the hotel's bikes for a quick ride around town. And kids will always get a kick out of the nearby Hesston Steam Museum and Captain Mike's Fun Park . For lunch, Redamak’s is the popular burger joint in the area, filled with fun activities for kids, including a mini firetruck. And what would a visit to a beach town be without ice cream? Don’t miss funky Oink's Dutch Treat Ice Cream & Yogurt Shop . For dinner, visit the hotel’s Terrace Room  for a comforting Italian dish like spaghetti and meatballs (described as Grandma’s family recipe with sweet marinara) that everyone will love. Or pop over to Bentwood Tavern for wood-fired pizza.

10.  Gurnee, IL

Driving time from Chicago:  45 minutes

If you’re taking the family up north for a day of fun and games at Six Flags Great America , why not make a weekend out of it? Aside from the amusement park, the village of Gurnee is also home to Great Wolf Lodge —a resort with an 80,000-square-foot indoor water park. Once you’ve dried off, shop ‘til you drop at outlet mall Gurnee Mills .

For even more activities, make the short drive across the border to Kenosha for America's Action Territory Fun Park , where you'll find everything from bumper boats and cars to laser tag and batting cages. The youngins’ can gaze at dinosaur fossils and learn about the link between the prehistoric reptiles and birds at the Dinosaur Discovery Museum , or climb to the top of Southport Lighthouse for sweeping views. There are also a ton of adventures to be had at the Bristol Renaissance Faire during the summertime, when fairgoers dressed in costumes converge on a recreated 16th century port city.

11.  Ottawa, IL

Driving time from Chicago: One and a half hours In just an hour and a half, you'll be transported to a beautiful setting filled with both water and land activities to keep your family entertained. Hike at nearby Starved Rock State Park  or Buffalo Rock State Park ; bike along the I & M canal trail that runs for more than 60 miles; take a dip in the on-site pool or build sandcastles and pack a picnic at the aptly named Picnic Grove. You can also rent a variety of boats, kayaks, water skis and canoes at a nearby private beach. Renting a cottage is the way to go, and you can find a lovely place to rest your head at Heritage Harbor .

12.  Battle Creek, MI

There are no picturesque tree-lined streets or Michelin-starred restaurants in the manufacturing hub nicknamed “Cereal City,” but it’s full of wacky family adventures. The home of Kellogg’s and Post Consumer Brands honors its origins with an annual CerealFest each June. If you miss it, venerate America’s favorite breakfast any time of year with a visit to The Calhoun County Visitors Bureau’s  "Cereal History" exhibit to journey through the history, manufacturing, and culture significance of Battle Creek native John Harvey Kellogg’s invention.

After some cereal nostalgia, meet rescued gators at the Critchlow Alligator Sanctuary twenty minutes south of Battle Creek. There are more than 180 alligators on site, including the 11-foot "Godzilla."( Don’t worry—staff only let the kids touch the small ones.)

Grab dinner a turkey buffet dinner at Cornwell’s Turkeyville USA and then stay for one of the venue’s rotating musicals or theatre performances. For those who prefer more traditional animal encounters, you can glimpse lions, zebras and giraffes at Binder Park Zoo .

As the sun sets over Goguac Lake, you can pretend you’re miles away from Southwestern Michigan at the ostentatious McMansion Paradise Island the Fantasy of the Nouveau Riche . Filled with regionally inappropriate nautical decor, this rental on the lake’s Clark Island sleeps 12, is only accessible by boat and features big windows that offer lake views.

13.  Northern Indiana

Driving time from Chicago: One hour and 40 minutes

With the charming university town South Bend as your home base, spend time exploring Northern Indiana’s outdoor expanses and Amish culture. Start with a visit to St. Patrick’s County Park , a 398-acre preserve with activities for any season. The park features year-round bird watching opportunities and hiking along the numerous trails of varying lengths, canoeing and kayaking along St. Joseph River in the summer and cross country skiing in the winter.

During summer visits, make time to browse outdoor markets running May through September. The South Bend Farmers Market and the Mishawaka Market  are both go-to spots for sampling local produce and artisanal cheeses and meats.

You can easily spend an entire day at Shipshewana Auction & Flea Market —the largest in the Midwest—located an hour drive east from South Bend. The size of more than 30 football fields, you’ll find antiques and vintage furniture, decor, apparel, food stalls, and even plants. On your way back to South Bend, make a stop in Middlebury, a town of around 3,500 with a strong Amish presence. Visit the original Rise ‘n Roll Bakery and Deli and grab a box of the notoriously addictive cinnamon caramel doughnuts.

14.  Springfield, IL

Driving time from Chicago: Three hours and 15 minutes

The capital of Illinois is full of history and things to do with the family. Tour the Old State Capitol —the spot where Abraham Lincoln announced his candidacy for the presidency—or visit the Abraham Lincoln Presidential Library and Museum to learn more about the nation’s 16th president and the American Civil War. Hit up sporting goods store SCHEELS for much more than just athletic apparel—the popular attraction also houses a Ferris wheel, 16,000-gallon aquarium, arcade and cafe. For some outdoor activities, the Henson Robinson Zoo is home to over 300 animals while Knight’s Action Park is a 62-acre water park with a mini golf course. 

15.  Walworth County, WI

If you’re looking for an off-the-beaten track destination to unplug and reconnect with nature, the Walworth County lakes within thirty five minutes of Lake Geneva are a no-brainer. At Delavan Lake, Whitewater Lake, Rice Lake, Lauderdale Lakes (comprised of three interconnected lakes) and nearby Lake Wandawega to the south and Pleasant Lake to the north, visitors can canoe, kayak, fish, swim and hike. Head south to the 12-mile White River Trail  for hiking, biking and horseback riding.

Whitewater Lake’s Scenic Ridge Campground  offers wooded or grassy campsites along the water, access to volleyball nets, horseshoe pits and hiking trails, plus an extensive calendar of sports, entertainment and activities for folks of all ages.

16.  Columbus, IN

Driving time from Chicago : Four Hours

You might be thinking “why would any kid enjoy a hub of modernist architecture?” However, this vibrant ode to inventive constructions can be appreciated by all ages. The vibrant pavement in the city center and colorful bridges are just enough to keep the kids captivated. If that’s not enough, a three-story children’s museum is always an option. 

A must visit in this eccentric town is Zaharakos Ice Cream Parlor and Museum , an authentic ice cream shop that opened in 1900. For dinner, family-friendly ZwanzigZ Pizzeria and Brewery has something for everyone. 

17.  Brown County, IN

Brown County State Park is famous for its vibrant fall colors, but this nature oasis 30 minutes northeast of Bloomington is fun during any time of the year. Indiana’s largest state park often referred to as the “Little Smokies” has 11 hiking and 14 mountain biking trails of varying lengths and difficulty levels—plus, 20 miles of roads for when your legs get tired—you can mix and match for your desired adventure, whether it's to see stunning views of rolling tree-covered hills and waterfalls or to feel immersed in the backcountry. If you need to rent two-wheeled transport, stop by Q’s Bikes .

There are plenty of campsites around the park, but for indoor stays head just outside the park boundaries to Nashville, a small town full of mom-and-pop craft stores, fudge shops, ice cream and restaurants with live entertainment. Cornerstone Inn has a campus of 41 affordable accommodations around town and a cabin in the woods. The delicious pizzas and craft beer at Big Woods are much needed fuel after an active day—and don’t skip the sizzling skillet cookie topped with ice cream.

18.  Galena, IL

Driving time from Chicago: Three hours

Words people use regularly to describe Galena include “quaint,” “charming” and “historic,” but none of those have to also mean “boring.” One of the best all-ages options for more active families is the Chestnut Mountain Resort , a 100-room lodge featuring skiing and snowboarding in the winter and ziplining and a 2,050-foot alpine slide in the summer. 

If you don’t want to go the resort route, there’s still plenty to do in the great outdoors with the whole family, from kayaking or canoeing down the Galena River with a rented vessel from Nuts Outdoors to a scenic trail ride with the Shenandoah Riding Center to strawberry picking at Terrapin Orchards . For a fun, family-friendly evening activity, catch some thrilling illusions at the P.T. Murphy Magic Theater or get your nostalgia on with a drive-in movie at the Midway Drive-In in nearby Sterling. And if you’re browsing through downtown Galena, don’t forget a stop for some sweets at Galena Kandy Kitchen . 

19.  Ann Arbor, MI

There are plenty of reasons to take a family road trip to Ann Arbor, even when it isn’t Michigan football or basketball season. Kids can spend hours at the interactive Ann Arbor  Hands-On Museum or the Leslie Science and Nature Center, where they can run around the Nature Playspace and get up close with birds of prey in the raptor enclosure, or snakes and frogs in the Critter House. The whole family will find something to love exploring the shops and restaurants on colorful Main Street—the little ones will be particularly drawn to the nostalgic soda and sweet shop Rocket Fizz and the countless shelves of books, comics, toys and games at Vault of Midnight .

As for going out to eat with your whole crew, even the breweries here cater to craft beer enthusiasts with kiddos— Blue Tractor BBQ & Brewery and Jolly Pumpkin offer award-winning brews and hearty, creative food for the parents, with solid kids menu options and crowd-pleasing desserts. Speaking of dessert, a trip to Zingerman’s Deli for their decadent brownies is also a must.

20.  Casey, IL

Just under a four hour drive from Chicago, the small town of Casey is home to some of the world’s largest items. From a 28-foot Chevy truck Key to a 46,000-pound rocking chair, these public sculptures are best seen in person. Stop by to see 12 of the record-holding world’s largest items. It’s a great day whenever kids feel like they’ve been shrunken down to the size of an ant.

Stay at the quaint and comfy Eighteen-Nineteen Sleepover Hotel while planning your sightseeing around the city. Locals love the Wildflower Bakery and Candy Company and it’s a great treat to keep the kids happy. For any java-dependent parents running on fumes, the Casey Coffee Company is conveniently located right between the World’s Largest Rocking Chair and the World’s Largest Mailbox.

Family-friendly day trips

Family-friendly day trips from Chicago

With new states to explore just a short drive away, Chicago is perfectly situated for a quick jaunt to regional wonders with the little ones in tow.

[image] [title]

Discover Time Out original video

• Press office
• Investor relations
• Work for Time Out
• Editorial guidelines
• Privacy notice
• Do not sell my information
• Cookie policy
• Accessibility statement
• Terms of use
• Copyright agent
• Modern slavery statement
• Manage cookies
• Advertising

Time Out products

• Time Out Worldwide

Time Out magazine