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  1. Enjoy a truly unique dinner and a show in Tommy Gun's Garage, one of Chicago's longest running dinner theatre show experiences! This amazing gangster themed establishment is set up to appear like an illegal speakeasy in the roaring 20s when mafia men and flapper girls dominated the city of Chicago.

  2. Celebrate the 1920s in Chicago, an era of gangsters, jazz and flappers, during this dinner performance of Tommy Gun’s Garage in the Windy City. This lively, fun-filled show, complete with plenty of crowd interaction, is a sure-fire crowd pleaser.

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    • Tommy Guns Garage
  3. Step inside Harry Caray's landmark building, once owned by infamous Chicago mobster Frank Nitti, and join us for dinner and TRUE CRIME HISTORY MYSTERY based on the real-life murder of Eddie O'Hare (Al Capone's lawyer and father of war hero Butch O'Hare for whom the airport is named).

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    • Attraction
    • 33 W Kinzie St, Chicago, 60654-4613, Illinois
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  4. Step inside our landmark building, once owned by infamous Chicago mobster Frank Nitti, and join us for a dinner & show filled with laughs, gangsters, audience interaction and toe-topping musical productions!

    • 33 West Kinzie, River North, 60654, IL
    • gangster ka show in chicago downtown1
    • gangster ka show in chicago downtown2
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    • Sit in Al Capone’s favorite booth. The Green Mill in Uptown was once best known as a former speakeasy and mob hangout for Al Capone and his gang run by Capone associate “Machine Gun” Jack McGurn during Prohibition.
    • Visit Harry Caray’s Steakhouse, former mob headquarters. Mob boss Frank Nitti’s apartment was once on the fourth floor of the building that is now Harry Caray’s Italian Steakhouse.
    • See where Dillinger was gunned down at the Biograph Theatre. After a tip-off from his girlfriend, notorious gangster John Dillinger, often called America’s first “Public Enemy Number One” was shot by federal agents on July 22, 1934.
    • Hear true tales of Chicago’s mob history. Whether you’re a Chicago local or on vacay, a guided tour is the best way to explore Chicago’s colorful history of mystery and mayhem.
  5. Dec 18, 2015 · So find a real-deal speakeasy and don your seersucker suit for a night of running rum (to your stomach) at these eight Chicago bars with insane mob connections.

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  7. A wall replica of St. Valentine’s Day Massacre, 1928 model “A” Ford car and pictures of gangsters and mafias are hard to miss. Without any doubt you will enjoy music of 1920s including songs of Cole Porter, Fats Waller, George Gershwin.

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