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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
“very informative cruising up and down the Chicago river...and then the highlight....passing through the lock out on to Lake Michigan.Very fun! Followed by a wonderful time out and back viewing the city skyline!”
If your feet need a break from the city streets, a short sightseeing cruise is the perfect way to see the best of Chicago without breaking a sweat. Offered regularly throughout the day, it’s easy to fit this tour...read more
“I’ve taken the architectural boat tour several times from other companies, but her pictures of the insides, and wealth of knowledge made it fascinating!”
Discover the lavish interiors of some of Chicago’s most spectacular buildings when you book this architecture-themed walking tour. Meet your guide in the Loop, and set off on foot. You’ll venture behind closed doors...read more
“In addition to visiting several iconic Chicago restaurants and sites and enjoying their delicious specialties, Gabe took us to several sites important to Chicago’s history and architecture.”
Stroll around the Loop with a guide, discovering Chicago's lively food scene, on this small-group walking tour. Learn about the city's history and culinary heritage from your guide as you stop at favorite local...read more
“Kevin was very kind, knowledgeable, and fun to listen to!”
“As a bonus, you can visit the center, a small museum where you can admire an incredible 3-D model of the city of Chicago the size of a large room, and buy beautiful things at the gift shop.”
Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic...read more
Go inside more iconic buildings than any other Chicago architecture tour. The Loop is not just famous for the L train circling downtown Chicago, it’s an iconic, vibrant neighborhood, steeped in history. Prepare to...read more
Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new...read more
“This is a great tour to see amazing work from Tiffany.”
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
“The tour itself was the perfect blend of indoors, outdoors and a ride on the L-train.”
Make the best of your visit to Chicago and explore the interiors of the emblematic Loop of Chicago downtown with a private licensed guide.You will enjoy a private tour and discover the hidden architectural treasures...read more
Discover Chicago's bold character through its beautiful landmarks and fascinating backstories on this thoughtfully designed tour of history, contemporary life and world-famous architecture. Guests will see iconic...read more