Chicago Trip Guide · Experiences
Make your trip your own. Discover memorable tours, explore the details, and find the experience that feels right for you.
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399 experiences
Explore experience ↗◷ 1 hr 30 min
Explore the highlights of Chicago’s Chinatown in just 90 minutes with our expert-guided History and Culture Tour. This tour takes you t
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Explore experience ↗◷ 1 hr 30 min
"Dive into adventure with us, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden ge
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Explore experience ↗◷ 1 hr 30 min
Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hi
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Explore experience ↗◷ 2 hr
With Crazy Dash, you'll use an app to explore Chicago in this exciting scavenger hunt! Use an app to find things around the city in any
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Explore experience ↗◷ 1 hr 30 min
Let’s Roam leads the way as the top app-led adventure hunt company! Explore the city’s top landmarks and uncover hidden gems while tack
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Explore experience ↗◷ 2 hr 20 min–2 hr 30 min
To me, one can appreciate a given building, or piece of public sculpture, far better when a tour guide explains the historical and cult
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Explore experience ↗◷ 1 hr 30 min
"Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and h
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Explore experience ↗◷ 1 hr 30 min
Dive into adventure with your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is
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Explore experience ↗◷ 1 hr 30 min
"Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and h
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Explore experience ↗◷ 3 hr
Take a spin through the Windy City on a bike tour and discover the most remarkable and world-famous sights. Hit the streets like a loca
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Explore experience ↗◷ 45 min–1 hr 15 min
This 45-minute self-guided walking tour explores the bizarre history beneath Wicker Park’s elegant surface. Led by a longtime resident,
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Explore experience ↗◷ 30 min–1 hr
The Bloomingdale Trail was built on a former railway line that once served as the industrial backbone of Chicago's north side. On this
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