Last Updated on March 26, 2024 by Caitlin

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While many travelers head to Chicago for sightseeing and shopping, the Windy City is also a popular launch pad for road trips that explore the Midwest.

Fabulous Road Trips from Chicago

Lake Geneva, Wisconsin

85 miles / 1 hr. 30 mins.
Less than 90 miles from Chicago, Lake Geneva is a short ride to a destination that feels like a world’s away. Take Interstate 94 West to Kenosha and pick up Wisconsin Highway 50 west. A resort town on an 8-square-mile lake, Lake Geneva is a charming town with a little bit of everything: spas and boutiques; outdoor adventures like canopy tours and boat rentals; and plenty of romantic restaurants and wineries. Walk a section of the 26-mile Lake Geneva Shore Path for quiet contemplation of the views of the lake below. In winter, visit the ice castles for a different kind of wintertime fun.

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Starved Rock State Park

99 miles / 1 hr. 45 mins.
Take Interstate 80 West and follow signs along Illinois Highway 178 to the state park. You can hike around dozens of sandstone canyons and hidden waterfalls and, while the forest is stunning in any season, spring’s wildflowers and fall’s vibrant foliage are highlights. If the trails are crowded at Starved Rock, try Matthiessen State Park, just a few miles south. In addition, Matthiessen offers a similar landscape and hiking trails that weave through the canyons and streams.

Saugatuck, Michigan

139 miles / 2 hr. 45 mins.
The coast of Lake Michigan boasts many a quaint lakeside town, but Saugatuck is especially picturesque. Interstate 90 (eventually I-94) takes you all the way around the southern edge of Lake Michigan and north to I-196 to the Blue Star Highway. Cross the Kalamazoo River on the only remaining chain-driven ferry in the country, and climb the 302 steps to the top of Mount Baldhead. Run down the dunes to the refreshing water of Oval Beach on the other side, but don’t forget you’ll have to climb back up!


164 miles / 3 hrs.
Head west on Interstate 90 toward Rockford, and take Highway 20 west until you reach Galena, one of TripAdvisor’s “Top Ten Charming Small Towns.” Stroll along Main Street for unique shops like an eclectic toy store, a root beer soda shop, and a hot sauce emporium with samples that’ll blow smoke out of your ears. In warmer months, consider taking a rafting trip or hike the bluffs nearby. Winter road trippers can hit the slopes at a nearby ski resort.

Door County, Wisconsin

244 miles / 4 hrs.
Hop on Interstate 94 (an easy jog from O’Hare) west to Milwaukee, then take I-43 north to the state highways that crisscross through drop-dead-gorgeous Door County. You won’t be able to see all of this 2,000-square-mile peninsula in one day, but you can take in its lighthouses, rocky shorelines, state parks, and quaint roadside cherry stands. If you make it all the way north to Sister Bay, stop at Al Johnson’s Swedish restaurant, which is famous for its Swedish meatballs and goats that love to play on the roof.

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St. Louis, Missouri

311 miles / 4 hr. 36 mins.

When you think of St Louis, it’s likely that one image comes to mind: the iconic Gateway Arch, created in 1966 to celebrate westward expansion under Thomas Jefferson. There’s lots to do once you arrive in St. Louis; you can visit the city’s iconic zoo, tour the Anheuser-Busch brewery, take in a ball game, or kick back in 1,300-acre Forest Park. >> Recommended hotels in St. Louis