Chicago is beautiful, but sometimes you need a change of scenery. Fortunately, there is plenty to see and do—you just need to hit the road. With many beautiful and unique vacation spots within a few hours’ reach, it’s one of America’s best cities for scenic road trips. From dreamy beachfront towns to cultural hotspots, the Windy City is a stone’s throw away from multiple adventures. We have gathered 15 bucket-list road trips from Chicago to explore this summer.
St Louis, Missouri
St. Louis boasts plenty of world-class attractions you can explore on a road trip from Chicago, starting with the Gateway Arch. This 630-foot-tall monument is the tallest arch on the planet and America’s tallest monument. Riding to the top of the arch is an experience you’ll never forget. Spare some time for Forest Park with its diverse experiences, including the St Louis Art Museum, St Louis Zoo, and the Missouri History Museum. The city’s breweries, culinary offerings, and wineries are fascinating.
- Distance: 297 miles
- Driving time: 4 hours and 6 minutes
Six Flags Great America, Illinois
Six Flags Great America is one of the best day trips you can enjoy from Chicago. With over 100 rides to enjoy, including 17 roller coasters, it’s perfect for families. Thrill-seekers will enjoy riding the Batman, the Superman, and the newly added Wrath of Rakshaa. There is an incredible variety of interactive games, culinary treats, and shows.
- Distance: 55.3 miles
- Driving time: 56 minutes
Springfield, Illinois
Illinois’ capital, Springfield, is known for its connection to Abraham Lincoln, who lived here from 1837 until 1861, when he gained the presidential seat. It’s one of the best stops along the historic Route 66, which runs directly through it. Catch a glimpse of Lincoln’s life and legacy at the Abraham Lincoln Presidential Library and Museum and the Lincoln Home Visitor Center. For outdoor adventures, visit Washington Park or Henson Robinson Zoo.
- Distance: 201 miles
- Driving time: 2 hours and 49 minutes
Eau Claire, Wisconsin
If the arts are your thing, you’ll enjoy a road trip to Eau Claire. Thanks to the city’s vibrant arts and cultural community, it’s dubbed “Indie Capital of the World.” It’s the hometown of the iconic band Bon Iver, along with its lead singer Justin Vernon, who made incredible contributions toward the town’s transformation. Nestled at the confluence of the Chippewa and Eau Claire Rivers, the city boasts plenty of outdoor recreational opportunities, from water adventures to a plethora of bike trails.
- Distance: 318 miles
- Driving time: 4 hours and 52 minutes
Door County, Wisconsin
Only four hours’ drive away, Door County is a charming slice of the Caribbean. While not a tropical destination, the pristine beaches, clear turquoise waters, and the relaxing vibe offer a unique coastal experience. Beyond its sparkling 300 miles of shoreline, you’ll find numerous parks and charming islands. The small towns dotting the area offer delicious food, unique shopping adventures, and thriving art communities worth your time.
- Distance from Chicago: 274.8 miles
- Driving time: 4 hours 46 minutes
Niagara, Wisconsin
Wisconsin’s Niagara is a charming small community famous for its natural beauty. The most interesting thing about its thundering waters is where it gets its name. The roaring Menominee River offers many opportunities for outdoor recreation, from whitewater rafting to scenic hikes. Another must-have adventure is a horseback riding experience via the Bjorkman Horse Outings. History buffs can learn about the town at the Niagara Historical Museum.
- Distance: 299 miles
- Driving time: 4 hours and 43 minutes
Traverse City, Michigan
Traverse is best known as the “World’s Cherry Capital,” but it offers much more than cherries. Stroll through the Village at Grand Traverse Commons for its historic charm, shopping, and dining opportunities. If you are road tripping with your family, take them to Clinch Park, where you’ll find a marina, picnic spots, and a playground for the kids. Explore the Bowers Harbor Vineyards or Chateau Chantal Winery for wine tastings. Don’t forget to learn about the local maritime history at the Mission Point Lighthouse, which has been around since 1870.
- Distance: 320 miles
- Driving time: 4 hours and 39 minutes
South Bend, Indiana
Home to the University of Notre-Dame, South Bend makes a brilliant road trip from the Windy City. The city is known for its lively arts and culture scene, and the South Bend Museum of Art and the Morris Performing Arts Center are iconic spots worth stopping by. If you are outdoorsy, visit the Potawatomi Zoo and stroll along the East Race Waterway. South Bend’s small-town feel and relaxed atmosphere make it a great spot to unwind.
- Distance: 95.7 miles
- Driving time: 1 hour and 36 minutes
Amish Country, Ohio
Amish County’s rich culture, unforgettable culinary offerings, and beautiful scenery make it a compelling destination for a trip from Chicago. With its rolling hills, expansive farms, and the slower-paced lifestyle of the locals, it’s the perfect place to unwind. The Farm at Walnut, the Amish Country Theater, and the World’s Largest Cuckoo Clock are some of the best attractions in the region.
- Distance: 350 miles
- Driving time: 5 hours and 50 minutes
Louisville, Kentucky
Louisville is known for the Kentucky Derby, America’s most famous horse race, which has been continuously running since 1875! Learn about this prestigious sporting event at the Kentucky Derby Museum. Beyond that, Louisville offers diverse travel experiences, from interactive exhibits at the Kentucky Science Center to breathtaking vistas of the Ohio River at Waterfront Park. Enjoy a mix of culinary adventures, distillery tours, and more along the iconic Louisville Urban Bourbon Trail.
- Distance: 318 miles
- Driving time: 4 hours and 56 minutes
Madison, Wisconsin
Madison’s blend of scenic natural beauty and urban experiences makes it a great place to explore. You can stroll through its bustling downtown and buy some local products at the farmers’ market. If you love history, learn about the city’s past through engaging exhibits and artifacts at the Wisconsin Historical Museum. Art enthusiasts shouldn’t miss the Madison Museum of Contemporary Art and the Chazen Museum of Art.
- Distance: 147 miles
- Driving time: 2 hours and 31 minutes
Lake Geneva, Wisconsin
The beautiful town of Lake Geneva and its surroundings offer a wealth of outdoor attractions and activities. You can swim, boat, and enjoy other water activities on the lake. If you want to stay off the water, there are plenty of beautiful hiking trails and golf courses for outdoor fun. You’ll also love the unique dining, cultural, and shopping opportunities in the town’s downtown area.
- Distance: 83 miles
- Driving time: 1 hour and 45 minutes
Cincinnati, Ohio
The nearly five-hour road trip from Chicago to Cincinnati is a worthwhile experience, thanks to the diverse scenery and attractions. It showcases a unique side of the Midwest as it meanders through many iconic spots, including national park sites like the Indiana Sand Dunes. While in Cincinnati, you’ll find plenty of things to see and do, from the scenic riverfront to cultural gems like the Cincinnati Art Museum and the Music Hall.
- Distance: 315 miles
- Driving time: 4 hours and 54 minutes
Rockford, Illinois
Rockford is only one and a half hours away from Chicago, making it an excellent day trip. The quiet and laid-back nature of the town offers the perfect atmosphere for relaxing and unwinding. You can do many interesting things while there, from strolling through the gorgeous Anderson Japanese Gardens to taking your kids to the Discover Center with its hundreds of hands-on exhibits.
- Distance: 92.7 miles
- Driving time: 1 hour and 29 minutes
Detroit, Michigan
Detroit is one of America’s most celebrated cities. It’s known for its incredible diversity, friendly locals, and a thriving arts and music scene. Visit the Detroit Institute of Arts (DIA), one of the best art museums in the country, with over 65,000 impressive artworks. Bike the Detroit Riverfront for scenic views and spend some time in Belle Isle Park, which features numerous attractions including a museum, a conservatory, and an aquarium. Don’t leave without trying the famous Coney Island hot dogs.
- Distance: 371 miles
- Driving time: 7 hours and 47 minutes
