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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.
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
Sightseeing in Chicago is especially entertaining with this nighttime crime history tour. A guide aboard the bus details the Windy City’s notorious mobsters, from Al Capone to Bugs Moran. It’s a fun and...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
See dozens of landmark buildings that line the Chicago River on the only architecture cruise lead by expert docents from the Chicago Architecture Center. The vessel—Chicago’s First Lady—is designed for prime...read more
Enjoy a private 2-hour walking tour with Belgian-American tour guide Leentje. She will introduce you to the city she calls home since 2014. Every tour is different and custom-made. Tours are available in English,...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
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
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
We wrote the book(s) on Chicago ghosts! Now in our 18th year!Ursula Bielski, our founder, has published more than a dozen volumes on Chicago's haunted history over more than two decades. Chicago Hauntings is the...read more
This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying architectural styles and see how older structures...read more
Chicago is the architectural capital of the country and has so many tours profiling these wonderful, beautiful buildings. Hiding around these architectural masterpieces, however, are UGLY BUILDINGS. This...read more