Chicago Trip Guide · Experiences
Make your trip your own. Discover memorable tours, explore the details, and find the experience that feels right for you.
Explore the collectionYour next great day out
399 experiences
Explore experience ↗◷ 2 hr
Step into the birthplace of the modern skyscraper on this immersive walking tour through Chicago’s historic Loop. Discover the stories,
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Explore experience ↗◷ 3 hr–7 hr
This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and
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Explore experience ↗◷ 3 hr
• Skip the lines and explore the world-renowned Field Museum with a ticket and a digital tour - all in one app • Get into an Ancient Eg
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Explore experience ↗◷ 2 hr
Uncover the chilling history of Chicago's gangsters and ghosts on this thrilling late-night Halloween walking tour. Delve into the dark
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Explore experience ↗◷ 1 hr
Rent a premium Yamaha VX jet ski and ride the waves on Lake Michigan with Rev & Ride Adventures. Offering flexible 1 hour ride times, t
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Explore experience ↗◷ 2 hr
Walk through Chicago’s vibrant Jewish history, from the striking Loop Synagogue to the inspiring Heald Square Monument and Jay Pritzker
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Explore experience ↗◷ 1 hr 30 min
Become an official Chicago Explorer with the Kids Loop Treasure Hunt. This engaging scavenger hunt invites young adventurers to navigat
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Explore experience ↗◷ 1 hr–2 hr
This self-guided bike tour traces Chicago's reinvention from the ashes of the Great Fire to the skyline that rose in its place, pedalin
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Explore experience ↗◷ 3 hr
Discover the local shopping scene and its fashion DNA with a professional stylist as you embark on a personalized shopping circuit buil
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Explore experience ↗◷ 1 hr 30 min–2 hr
Downtown Chicago has a dark history hiding in plain sight. This self-guided audio tour takes you through the Loop on your own schedule,
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Explore experience ↗◷ 35 min
Book your private arrival transfer from Chicago Midway Airport (MDW) to Chicago. Avoid the hassle of waiting in long taxi or shared shu
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Explore experience ↗◷ 50 min
Book your Private Round-Trip Transfer from Chicago Midway Airport (MDW) to Chicago or address and return. Don't go through all the hass
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