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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
“Very informative and entertaining - the tour guide Andy was excellent, views were outstanding, bar on board for refreshments and could sit downstairs in the shade when the July sun got too much!”
Explore all three branches of the Chicago River on a journey through the heart of the city. This riverboat excursion introduces passengers to Chicago’s legendary architecture, narrated by a professionally trained...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
“Once in Chicago we took a river boat tour that showed us insights of the city that ended up at spectacular Lake Michigan, which allowed us to admire the impressive city skyline as sailors arriving at a mystical land.”
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
“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...”
“This was the perfect way to get an overview of the city and its sights and get some excellent recommendations for good places to eat and drink!”
“Walking pace between food stops was just right, food choices were scrumptious, and history narratives, views of the river, architecture, and choice of stops superb!”
Combine tastes of Chicago's most famous foods with stops at local must-see landmarks on a single tour. Instead of spending the day chasing down these foods and highlights on your own, save valuable vacation time by...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
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
“Downtown Chicago is a fabulous place to visit, but you haven’t seen it till you’ve taken a tour of the river that divides it and helped it become the City it is today, A view from the river puts the history and th...”
Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages...read more
“A fabulous and must see view of the architectural genius that defines Chicago and a refreshing cruise on the lake topped by an informative, witty, well delivered narration by our tour guide: Cameron, are what you...”
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
Our Chicago Foodie Lovers Tour will take you to the most iconic and delicious spots in Chicago all in one day. If you are looking for a little bit of culture, great photos, and a ton of delicious food then this is...read more
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
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
“Daniel O Connell was our tour guide today and we were very impressed with his knowledge of Chicago events, shadey spots to stop and regroup, as well as interesting facts and stories about the area we covered today.”
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
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