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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
To truly appreciate Chicago's famous skyline, admire it from the water on this top-rated Lake Michigan architecture cruise. While most sightseeing boats remain on the Chicago River, this one gives you a panoramic...read more
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
Set sail along the Chicago River and admire the city’s ever-changing architectural landscape from the water as you cruise through the Windy City. Listen as your guide points out key landmarks such as the Wrigley...read more
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
Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic...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
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
See Chicago the Island Party way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax an enjoy a beverage. Have questions about buildings? Our helpful staff will be...read more
Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations...read more
This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the totally weird stories of Chicago. We will travel back through the ages as you...read more
The Sunset Cruise departs from the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. Enjoy the beautiful City architecture from the best vantage point in Chicago. The vessel will then navigate...read more
See Chicago's architecture from the best possible vantage point―a boat on the Chicago River―during this architecture-focused tour through the city's heart. Listen to your guide's in-depth commentary as you pass more...read more
Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and...read more
Windy City Dueling Pianos combines high energy live music played on two pianos by two highly skilled entertainers with hilarious, interactive comedy! Enjoy the show on one of our premiere boats with full bar, views...read more