As much as we all love the Windy City, sometimes we might need a change of scenery to spruce things up.
Don’t have the time to spend days planning a trip, packing up and traveling? Worry no more. We’ve got you covered with the best day trips to take from Chicago.
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Step into a world of Art in Madison, Wisconsin
Stimulate your senses at The Chazen Museum of Art, located two and a half hours away at the University of Wisconsin-Madison. With rotating, temporary exhibitions, every visit is sure to be unique. The best part: it’s free! If you’re still hungry for more art, head to the State Capitol and check out the historic grandeur of the Capitol of Wisconsin. Finally, one cannot simply leave Wisconsin without enjoying some of the finest cheese curds in the country! End your trip in Madison at Heritage Tavern for a meal that you won’t forget!
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Take a swig at Urbana-Champaign
Yes, we’re cheating a bit here by including two cities, but hear us out! The cities of Urbana and Champaign are linked so closely that it’s difficult not to package them together. That’s fine by us because, in only two and a half hours, you can get the luxury of two cities. With that said, there’s hardly a better place to go for some great booze. Riggs Beer Company and The Blind Pig make Urbana-Champaign a beer-lover’s dream. Pick up some fresh produce at the Champaign-Urbana Winter Farmers Market, or if you’re feeling like being outside, go boating at Crystal Lake Park.
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Located only an hour and 40 minutes from Chicago, the River Lights Plaza in South Bend is a must-see sight for any visitor. Watch in awe as vivid colors wash over the St. Joseph River. Consider what time of year you visit South Bend, if you want to see the River lights. The colors shown can actually change depending on the day or occasion (Green for St. Patrick's, red, white and blue for July 4th, etc). College football fans can rejoice, too, because Notre Dame isn’t too far from South Bend. If possible, try to catch the Fighting Irish at a home game. On the museum side of things, The Studebaker National Museum provides a deep insight into the history of design and industrial innovations!
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Go for a Wild Ride in Zion
Zion, Illinois, easily provides a full day of fun activities. An hour’s drive from Chicago, perhaps Zion is best known for its proximity to Six Flags Great America in Gurnee. This is definitely the spot for those seeking a thrill out of their day trip. If you’re not feeling the chaos of amusement parks, head over to Edge of Escape Rooms, one of Zion’s premier escape room experiences. Put your thinking cap on and test your limits in some of the best escape rooms in the country. If you’re in the mood for something with lower stakes, consider taking a relaxing walk on Zion Beach.
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No two days are the same in Woodstock
Woodstock, Illinois, is famously known as the shooting location for the cinema classic Groundhog Day. Luckily for us, the famous film location is only an hour and 15 minutes away! The city holds its own Groundhog’s Day Festival every year, complete with trivia about the filming of Groundhog Day and a tour of the shooting locations. If you’re looking for something else to do in Woodstock, the Pleasant Valley hiking and nature trails are five miles of gorgeous, natural sights. In the winter, you can even go cross-country skiing on the solar-lit trail.
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Take a dip at Centennial Family Aquatic Center
Located in Wilmette, Illinois, the Centennial Family Aquatic Center, a family-friendly water park, is a great way to cool off. The nearby ice rink and tennis courts mean there’s a lot of entertainment in Wilmette for a drive that’s less than half an hour. While you’re in Wilmette, stop by the Bahá'í temple to view the only Bahá'í house of Worship in the United States. Explore the exquisite architecture of the temple, as you take a moment to reflect on your mindfulness and spiritual reality. The best part? It’s only 40 minutes from home sweet home.
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Rev your engines for Milwaukee
Love motorcycles? If you do, then the Harley-Davidson Museum is for you. In only an hour and a half, you can make the trek to check out a variety of badass bikes or find out the story behind one of America’s oldest motor companies. On Saturdays, you can even stop by the museum for some BBQ, bourbon, and live blues music. If you’re looking for an interesting way to discover more about the city, Milwaukee Ghost Walks might meet your needs. This walking tour unveils the haunted history of some of Milwaukee’s Third Ward. The tour is built completely around information from real paranormal investigations, so prepare to be spooked. Lastly, The Jazz Estate is a great place to kick back, order a cocktail, and listen to world-class jazz music.
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Seasonal ~ Rule the Winter with Ice Castles in Lake Geneva, Wisconsin
We know winter can be brutal in Chicago, but who says you can’t have any fun with it? It only takes around an hour and 40 minutes to arrive at Lake Geneva, where you can have a ton of fun in the Ice Castles. Lose yourself in ice mazes, zoom down ice slides, and get ready for an exhilarating time in Lake Geneva. If you’re looking for something a bit less cold, take a dip at the indoor Timber Ridge Waterpark. Wanna take it a bit slower? The Lake Geneva Shore Path can provide some marvelous sights to end your trip on!
Updated June 2025
