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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.
“Our "docent" was Nick, and he is a first-class raconteur: very glib, entertaining, personable, knowledgeable, and passionate about Chicago and the marvels of structural engineering that define the skyline.”
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
“The night tour was great and James was an amazing tour guide who did all these extras to make the ride fun, like light strings and a bubble gun! Perfect views during the day and at night!”
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
“This tour offered a local perspective of Chicago so it totally didn’t feel like a scripted tour at all. Kelly gave us interesting and unique facts about Chicago’s architecture and transportation and history, even...”
“Our tour guide Matt was hilarious!!! Amazing night time views.”
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
“Our tour guide Dave was incredibly knowledgeable about the history of the city and was able to fill our tour with fun facts about the buildings and neighborhoods we explored.”
Welcome to Chicago! Here in the Windy City, we've got outstanding architecture, inspiring public art, a fabulous downtown district, and so much more. Come along with a local guide to check out some of the Must See...read more
“His knowledge of Chicago was vast and he made every part of the tour intriguing.”
Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish!Our two-part tour begins by exploring the heart of downtown Chicago - with its...read more
“Our guide was friendly and informative and we were able to eat some amazing food along the way.”
“The tour was interesting and informative with a nice combination of commentary on architecture and a visit to many featured attractions ... strongly recommend!”
Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Art Institute of Chicago, Willis (Sears)...read more
Chicago's Riverwalk is a bevy of impressive buildings, gardens, eateries, and beyond. Spend two hours wandering with an expert local at your side. Explore the art, architecture, and all the little hidden spaces with...read more
Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurants during the summer months, seating areas to relax,...read more
Are you looking for a way to see Chicago without joining a tour group? Explore at your own pace with this affordable walking tour.• Take in Chicago’s concrete giants and hear fascinating stories about quirky...read more
“Our guide was super fun, friendly and knowledgeable.”
Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a little bit of culture, some amazing architecture, & a ton of great photos then...read more