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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
“Great tour guide Joe, lots of good places and gave passengers some decision making ( zoo or Portillo's for food).”
Get a grand overview of Chicago on this half-day tour that ventures beyond downtown to both the North Side and South Side. With included coach transport, you don't need to rent a car or tackle traffic to see...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
“I got a great handle on what makes Chicago Chicago, while also learning about the buildings, the hiatory, the food traditions and comfort food of locals, and plenty of insight into the life and mindset of the ever...”
“He drove us from the Loop, to the Chicago River, up the Magnificent Mile, the Rush Street restaurant area, a children's farm next to the Zoo, the length of huge Lincoln Park, and back along beautiful Lake Shore Dr...”
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
“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...”
“We had bill and he was the best so Knowledgeable about Chicago history and all of the food we were eating!! Everything was great, big portions everyone was stuffed by the end of the tour!! Highly Recommend this to...”
Chicago's famous food scene is a huge part of its identity but finding the best of all the options can be daunting. Let a foodie-guide show you the way on this culinary-focused tour of the River North neighborhood....read more
“Very fun and informative, great tour guide, convenient photo op stops.”
PLEASE NOTE: Our mini buses are disinfected after each tour. We will do our best to make each tour fun, informative and as SAFE as possible!Freshly discounted private tours are also available. They will be the best...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
“Fun foods that will fill you up....we weren't hungry for dinner until about 10 pm! Kelly was a great guide providing her knowledge of the restaurant scene and Chicago lore as we walked between classic food destina...”
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 (now including Wrigley Field!) and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus,...read more
“We live in Woodstock, IL and these tours are a great way to reconnect with the big city.”
“Sarah will teach you how to ride in minutes, and then off you go on an architectural tour of the city along with the sights of Grant Park, the Riverwalk, and the Chicago Shoreline.”
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
Downtown Chicago is filled with gems. Some famous, others known only by select locals. Many of these spots are best seen on foot as opposed to a moving vehicle. We'll take you inside several of these architectural...read more
See Chicago the best way possible, in a PRIVATE open top Jeep Wrangler. Fun, informative, cool music, top guides, best routes, customizable too.Sanitized after each trip to do our best to protect everyone. Masks...read more