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.
Transporting a group? Backed by extensive industry experience and a vetted network of trusted operators, Bus.com has curated a list of the top charter bus companies in Chicago - making it easy to find reliable group transportation in the Windy City.
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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 Urbana Farmers Market or the Champain Farmers Market, or if you’re feeling like being outside, go boating at Crystal Lake Park.
Take a stroll in South Bend, Indiana
Located only an hour and 40 minutes from Chicago, the Fridays by the fountain in South Bend is a must-see event for any visitor. Held every Friday through August. Enjoy live music, food trucks, and free community fun. For all my nature lovers, Shiojiri Garden isn't too far from South Bend. A Japanese Garden with 20 different varieties of large plants, over 200 large boulders, a donated statue and a teahouse pavilion. 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. Just an hour drive from Chicago. 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 Illinois Beach Hotel, for a relaxing stay while enjoying some lakeside dining. If you’re in the mood for something with lower stakes, consider taking a stroll along the Waukegan Municipal Beach.
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No two days are the same in Woodstock
Woodstock, Illinois, is always throwing in 100's of events in the square. Park in the Square has different events almost daily, from city bands to movies in the park. If you’re looking for something more quite, the Pleasant Valley hiking and nature trails are five miles of gorgeous, natural sights. In the summer, you can even go paddle boarding and kayaking in the river and lake.
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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. 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 ~ Live Like Royalty at the Renaissance Fair in Bristol, Wisconsin
If entertainment is what you're looking for, The Bristol Renaissance Fair has tons of it. For the first time you can say you watched a jousting match and walk along with peasants or royalty. Grab a giant turkey leg and join the pub crawl that's filled with jokes, stories, and riddles. Only 30 minutes out you can have a relaxing beach day at Lake Geneva. Stop at The Riviera Beach and take a dip in the lake or step away to the restaurants nearby. If you’re looking to avoid a sunburn, 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 2026
