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 ↗◷ 35 min
Take the worry out of your arrival to Chicago (ORD) Airport and pre-book a private transfer to suit your group size (up to 14 people).
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View datesExplore experience ↗◷ 35 min
Take the worry out of your departure to Chicago Airport and pre-book a private transfer to suit your group size (up to 14 people). Avoi
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View datesExplore experience ↗◷ 35 min
Take the worry out of your departure to Chicago Airport and pre-book a private transfer to suit your group size (up to 14 people). Avoi
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Explore experience ↗◷ 2 hr–2 hr 30 min
Chicago is inseparable from its Black history, where local pioneers helped shape the city’s story. On this self-guided audio tour throu
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Explore experience ↗◷ 336 hr
Travel the legendary Route 66 in 14 unforgettable days - from Chicago to Los Angeles across eight states, discovering over 450 handpick
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Explore experience ↗◷ 144 hr
Route 66, known as "The Main Street of America", runs through eight states from Chicago to Santa Monica. EN route to Illinois, POR Miss
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Explore experience ↗◷ 2 hr
Starting near Vietnam Veterans Memorial in Chicago, complete Wacky Walks by using an app to find a list of objects around the city and
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Explore experience ↗◷ 35 min–1 hr
Arriving at your destination is effortless with Deenil Experiences’ airport transfer service. Enjoy a smooth ride in a clean, luxurious
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Explore experience ↗◷ 1 hr 30 min–2 hr
Chicago's prettiest neighborhood hides some of its darkest history. This self-guided audio tour takes you through Lincoln Park on your
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Explore experience ↗◷ 1 hr 29 min
Discover how a city of rigid steel and glass skyscrapers transformed its streets into a world-class, democratic art gallery. On this im
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Explore experience ↗◷ 2 hr
Skip the lines to the iconic Art Institute of Chicago and marvel at world-famous masterpieces by Monet, Van Gogh, and Picasso. Dive int
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Explore experience ↗◷ 2 hr 30 min
Explore Chicago with a passionate local guide on a small-group walking tour that takes you beyond the city's most recognizable landmark
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