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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.
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
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
Combine a Chicago history lesson with supernatural tales for an ideal activity for adults and kids. Go back in time on the Gangsters and Ghosts tour to hear about Chicago in the roaring 1920’s when speakeasies...read more
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
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
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
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
We are Chi-Town foodies of the first order, and we're so excited to share with you all the culinary delights this historic Midwestern city has to offer. There is so much to share about Chicago: historic enclaves,...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
Get close to Chicago's most important monuments and parks on a top-rated bike tour that travels entirely on the city’s abundant bike paths, so there's no need to worry about traffic. Pedal through Grant Park, along...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
Learn about Chicago’s haunted past and see its mysterious sights as you glide through the city on a Segway at night! Venture through the dark with your local guide, and see alleys, hotels and sites of some of the...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
What an amazing experience you will have on this One of a Kind Private Sightseeing tour! We will explore the wonders of Chicago from a 46-foot Private Yacht.Chicago's newest Harbor has been adorned with new...read more
If you're looking for an exciting and stress-free day exploring the wonders of Chicago, then this is the tour for you. We can’t wait to show you around!The morning will start with a private pickup from your hotel by...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
The Chicago Showcase Helicopter Tour is our most popular flight, perfectly combining amazing sights with plenty of time to soak it all in! This tour includes a breathtaking 15-minutes of flight covering almost every...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
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