Chicago's Original Gangster Tour at Chicago Walking Tours

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Hear stories about historic figures and visit historical sites

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Learn about Chicago as it was during the 1920s and 1930s. Guides explain the events and activities of Prohibition-era Chicago, highlighting the stories of historical figures such as Capone, Moran, and Dillinger. Visit notable sites, including the location of the St. Valentine’s Day Massacre, the Biograph Theatre, and the Holy Name Cathedral. The tour includes informative commentary and actors portraying figures from the time period.

Why you'll love it

  • Explore Chicago's most notorious gangster history on foot
  • Visit authentic historical sites tied to organised crime
  • Hear stories about iconic figures from Chicago's past
  • Uncover the real history behind the city's gangster era

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Age suitability
Recommended for ages 12+

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