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Chicago Gangsters

The “Roaring 20s” was a time of prosperity and celebration throughout America, but under the cover of Chicago’s vibrant veil, leagues of criminals continuously brewed trouble in the city. Al Capone and the Chicago Outfit gangsters took control of the streets with a hard hand and a deadly machine gun. The reign of Chicago gangsters in the early 1900s left an eternal stamp on the metropolis with the abundance of crime, bootlegging, and brothels.


Chicago Gangsters guides

Chicago Gangsters: History

Legendary tough guys such as Al Capone made Chicago the home to America's first gangsters. These hardened hooligans left a permanent mark in the history books of this bustling city by coining the Windy City as their center of operations for organized crime. 

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Chicago Gangsters: Tours

Only an exceptional crew of gangster connoisseurs could pack all of the history, excitement, and scandal of the 1920s into an interactive tour. These whirlwind tours give guests an insider view of the complex inter-workings of Chicago's gang system and even provokes the electric feeling of a dangerous gangster adventure.

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Chicago Gangsters: Restaurants & Clubs

Be taken back to the 1920s by participating in one of the Chicago gangsters’ favorite activities: eating and drinking (illegally). Restaurants all over Chicago have discovered that once upon a time their bars where actually underground speakeasies. Many of these eateries play up this theme by adding antique Prohibition relics, aged black and white photos of ill-famed criminals, and even specialty gangster menu items.   

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