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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
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
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
Chicago offers amazing historical and culinary adventures, and this bike and food tour allows you to experience both while leaving the navigation to a guide. Hop on a provided bike and pedal around 13 miles (21...read more
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
Welcome to Chicago! Here in the Windy City, we've got outstanding architecture, inspiring public art, a fabulous downtown district, and so much more. Come along with a local guide to check out some of the Must See...read more
Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish!Our two-part tour begins by exploring the heart of downtown Chicago - with its...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
Everyone does a boat tour when they come to Chicago -- it's "the thing to do." But how many people ever get BEYOND that? Imagine all the amazing interiors just waiting to be explored! This 2-hour walking (*not...read more
Are you looking for a way to see the wicked city without joining a tour group? Explore at your own pace with this affordable walking tour.• Find the city’s dark side with stories of opium trade, the city’s first...read more
Chicago’s Pedway is a system of underground tunnels and passageways that are laid out underneath the city so you can get from one end of the Loop to the other without ever going outside. We begin at the Cultural...read more
Welcome to Chicago, the city with rich culture, architecture, and art!This self-guided audio tour of Chicago will take you to must-see sights showing you the city from the best angles and telling its most exciting...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