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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
Are you looking for a way to see Chicago without joining a tour group? Explore at your own pace with this affordable walking tour.• Take in Chicago’s concrete giants and hear fascinating stories about quirky...read more
Immerse yourself along the Chicago River and admire the astonishing architecture and landmarks that have shaped the Windy City and beyond.Our expert guides will show you Chicago through a new lens and explore this...read more
This tour explores a worldwide phenomenon called “Dark Tourism” — the field of interest in visiting sites of death and tragedy. On this 2-hour walking tour, we will cover the real stories behind some of Chicago’s...read more
Join us for a family-friendly fireworks cruise on the Chicago River! Listen to seasonal music and celebrate the kick-off of the holiday season. Alcoholic and non-alcoholic beverages are available for purchase and...read more
Discover Chicago by private boat with a local Chicagoan to highlight its fascinating history and architectural marvels along the way!Before we board, we’ll take a short walk in the Chicago Loop, a bustling area...read more