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
SaleRegular price $39.00 CADUnit price perWander through colorful sculptures, charming boutiques, and local eateries before discovering breathtaking riverside gems that are so photo-worthy, your camera roll is sure to fill up!- Accessible
- Kid-Friendly
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Falls, Forests & Fables
SaleRegular price $39.00 CADUnit price perGet ready for a day filled with charm and easy winter adventures. Start in a small town bursting with colorful murals, then take in riverside lookouts, snowy trails, 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 CADFrom snow-dusted lakeside views and quaint small-town charm to playful animal encounters and a whimsical museum, this captivating road trip promises unforgettable moments for everyone in your group.- Kid-Friendly
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Lakeshore Views & Brews
$65 CADStroll 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
