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Tours, activities and experiences bookable on Tripadvisor, ranked using exclusive Tripadvisor data including reviews, ratings, photos, popularity, user preferences, price, and bookings made through Tripadvisor.
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Tours, activities and experiences bookable on Tripadvisor, ranked in alphabetical order.
Get views of Chicago’s most famous buildings, as well as insider info from an expert guide, on this architecture-focused cruise. See all the most important buildings on one tour, a hard-to-accomplish task on foot....read more
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Known as a world-famous hub for architecture, art, and politics, the lakeside city of Chicago has a wealth of must-see sights. Know exactly where to go in the Windy City on this hop-on, hop-off bus tour, complete...read more
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Check many Chicago landmarks off your must-see list on this small-group sightseeing tour aboard a minibus. Cover more ground than on foot, and hit lots of highlights over the tour. See Museum Campus, the Rookery,...read more
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See the beauty of Chicago from a new vantage point by going on this scenic cruise along the Chicago River and Lake Michigan shoreline. It’s a great way to spot multiple top Chicago landmarks in a short space of...read more
See dozens of landmark buildings that line the Chicago River on the only architecture cruise lead by expert docents from the Chicago Architecture Center. The vessel—Chicago’s First Lady—is designed for prime...read more
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Named for the cable car turnarounds and the prominent elevated railway that encircled the area at the end of the 19th century, the Loop is Chicago's commercial and cultural core. On today's epic scavenger hunt of...read more
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$2 Mimosas All Day! Sundays are Fun-Days aboard the floating tiki bar. See the Chicago River the Island Party way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax...read more
Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic...read more
Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish...read more
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Are you looking for a way to see the wicked city without joining a tour group? Explore at your own pace with this affordable walking tour.• Find the city’s dark side with stories of opium trade, the city’s first...read more
Everyone does a boat tour when they come to Chicago -- it's "the thing to do." But how many people ever get BEYOND that? Imagine all the amazing interiors just waiting to be explored! This 2-hour walking (*not...read more
Spice up your visit to Chicago on this in-app audio tour through the creepiest places of the city of lights!Explore the most haunted sites and buildings securing tragic and mysterious stories of Chicagoans. Hear...read more
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See Chicago Fireworks the Island Party way. Our floating Tiki Bar offers you the unique opportunity to see the sights of the Chicago River, topped off with a fireworks show. Have questions about the buildings you'll...read more
Enjoy $2 mimosas (all day) and beautiful views of the Chicago skyline aboard our flagship vessel. Enchantment boasts a Tiki Chic vibe, two climate controlled decks, two bars, two bathrooms, premium sound system,...read more