Top Chicago Historical & Heritage Tours

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus.
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Ready to discover some of the best Chicago has to offer with a local by your side?
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Interested in exploring Chicago from the perspective of ghosts and gangsters?
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Let us put the Custom in Chicago Custom tours… What are your must-see venues?
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Experience the best travel stories for yourself!
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Join us for a fun night of exploring Chicago's crime history on this 2-2.5-hour bus tour that includes: * World famous crime scenes like the St Valentine's Day massacre * Stops on-and-off the bus at famous crime sites * True Crime history * Historic video footage * Interactive live commentary * Crime quiz * Souvenir pamphlet with photos * Luxury climate-controlled bus * So much more!
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Our guides present an accurate account of the activities in Chicago during the 1920's and 1930's (Prohibition Era).
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This tour will take you past all the sights of Chicago’s Scenic North Side.
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This comprehensive half-day tour of Chicago is the perfect introduction to the Windy City!
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Go on a history-filled journey, from the inception of this majestic venue in 1921, all the way to its present-day incarnation as a premiere entertainment venue.
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Take a tour of Chicago and visit the 360 Chicago (John Hancock Observatory)!
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Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks below Chicago’s busy streets.
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Experience the vitality and excitement of Chicago on this sightseeing tour!
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Chicago and the history of the mob are synonymous when we look back at history.
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Looking for fun things to do in Chicago?
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This is a comprehensive tour of everything Chicago has to offer.
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Take in the world-famous skyline of the Windy City from the water, and enjoy a leisurely trip on Lake Michigan.
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Up for more of a spooky perspective of the Windy City?
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Learn about Chicago’s haunted past and see its mysterious sights as you glide through the city on a segway at night.
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Explore some of the most stunning interior spaces you’ll ever see – spaces you’d surely pass by without a second glance if you weren’t shown them by a seasoned, in-the-know tour guide.
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See Chicago’s most essential landmarks from the comfort of a private vehicle on this 3-hour jaunt around town.
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