Road Trips near Chicago
Choose a road trip that suits your driving and travel preferences from our selection below. Can't decide? Take our road trip quiz for personalized recommendations.
How does it work?
Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.
See our road trips below, or check out our quiz and trip map to help find your perfect adventure.
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A Riverside Ramble
$65 USDA scenic Chicago-area road trip with art, boutiques, eateries, and riverside views.- Accessible
- Kid-Friendly
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Falls, Forests & Fables
$65 USDGet ready for a day filled with charm and easy outdoor adventures. Start in a small town bursting with colorful murals, then enjoy riverside lookouts and even some surprising wildlife. This trip is perfect for those who love to stay active while exploring!- Dog-Friendly
- Kid-Friendly
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All Things Charming
$65 USDFrom serene lakeside views and quaint small-town charm to playful animal encounters and a whimsical museum, this captivating road trip promises to create unforgettable memories for everyone in your group!- Kid-Friendly
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Lakeshore Views & Brews
$65 USDStroll along a breathtaking boardwalk, dip your does in the cool water, sip craft drinks in unique destinations, and take lots of funky photos! This road trip will certainly let you unwind from the hustle and bustle of the city.- Kid-Friendly
- Accessible
