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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.
“He was very knowledgeable and answer all questions he made the ride interesting and fun! 10/10 recommend when you book ask for Clifton to be your host!”
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
“Even got cheese caramel popcorn at the Chicago theatre!! Eric was great!!! Fantastic tour: highly recommend & I’m a native Chicagoan!”
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
“We really enjoyed the guided tour of Chicago's historic crime scenes and although many places have changed since the time the crimes took place, Leah, our guide's vivid description made it interesting and fun.”
Chicago has a past filled with big gangster names such as John Dillinger and the infamous Al Capone. Dive deep into the city’s mobster ways with a guide who knows where “the business” was done. Stay comfortable...read more
“As the other tours from the Chicago Architecture it was a great tour and gave valuable insights about the buildings along the Magnificent Mile and their history.”
Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier shopping district. Hear the secrets and stories behind the striking...read more
“Our tour guide, Lara was very friendly, informative and did everything possible to make the tour fun.”
“The tour was very informative and the stops for photos was great Our driver Rick was very friendly and funny The boat tour was also very informative and the crew was great I would definitely recommend this tour to...”
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
“We loved the sites that we saw from Grant Park, The Stock Exchange, the view of the skyline, Duncan's Toy Chest, the World's largest Starbucks, Lincoln Park, the Chicago River and the Playboy Mansion.”
“I loved just being able to know little facts about the city and it’s neighborhoods, Gabe is a great tour guide made us feel safe riding around the city and answered all of our questions.”
Explore the lakefront districts of Chicago's North Side on a bike tour along quiet streets and waterside paths in the Windy City. You cover ground quickly as you pedal with your guide from Lake Shore Drive to the...read more
Flytographer Private Vacation Photo ShootConnect with a local hand-picked professional photographer in Chicago and capture your most memorable moments during this private photo shoot. Get insider tips on the best...read more
Choose the number of hours and we can help you make the most out of your time! Book a VIP treatment to see the city in your private car. Our knowledgeable drivers will do the hard work so that you an enjoy the view....read more
Welcome to Chicago! Here in the Windy City, there’s got outstanding architecture, inspiring public art, and a fabulous downtown district. Come along with a local guide to check out some of the Must See spots in...read more
“Our guide was super fun, friendly and knowledgeable.”