Tommy Gun’s Garage

7 January 2020


Chicago is no stranger to venues with deep-seated gangster pasts. While everyone knows and loves The Green Mill jazz lounge in Uptown, a renowned Al Capone favorite hangout, not far from 1000M, there’s a little known spot in the South Loop with an equally fascinating history. Tommy Gun’s Garage is an interactive speakeasy that dives deep into its gangster roots… through musical comedy.

From Gangster Past

Tommy Gun’s Garage is located on the site of where notorious gangster Big Jim met his unfortunate end. Giacomo Vincenzo “Big Jim” Colosimo was an Italian immigrant, and the leader of the Chicago South Side gang before Prohibition. From humble crime beginnings as a pickpocket, he eventually worked his way up to build the infamous Chicago Outfit, which lasted more than a century. Big Jim’s own crew even included Johnny Torrio and Al Capone himself.

Johnny Torrio was an enforcer, imported directly from New York by Colosimo to join the outfit. As an enforcer, Torrio’s role was to handle those who didn’t agree with the Chicago Outfit’s policies. Meanwhile, Torrio himself was outspoken against Big Jim. When Prohibition went into effect in 1920, Torrio pushed for the gang to enter the bootlegging game, though Colosimo refused. In May of that same year, Colosimo went to receive a shipment reported to him by Torrio, only to be ambushed and murdered. It’s suspected that Torrio organized the killing, and some even theorize that Al Capone, one of Torrio’s henchmen, was the gunman. As the story goes, eventually the site of Big Jim’s death became Tommy Gun’s Garage.

Tommy Gun’s Garage

Tommy Gun’s Garage is a speakeasy experience that transports guests back to the 1920s. At this interactive speakeasy, guests first enjoy a delicious sit-down dinner from a fixed price menu that includes Italian home-classics such as lasagna and prime rib. Dinner is, of course, accompanied by hooch — craft cocktails, martinis and beers fit to please a Prohibition Mob boss. Dinner is followed by a show, featuring gangsters and flappers dancing and singing the Charleston and other musical selections from the Roaring 20s. 

To learn more, or make a reservation for dinner and a show at Tommy Gun’s Garage, visit their website, here

Tommy Gun’s Garage is located at 2114 S Wabash Ave, Chicago, IL 60616.