Chicago Gangster Tours

Chicago Gangster Tours.

Experience real Chicago gangster culture on one of the city’s s Chicago Gangster Tours. Learn about legendary Chicago gangsters, like Al Capone and John Dillinger, who shot their way to celebrity status in the Windy City during the Prohibition-era. Immerse yourself in Chicago’s exciting gangster culture by touring the infamous sites that illuminate gangster fact and fiction- from the Biograph Theater to Union Station.

The Biograph Theater

- Visit the Biograph Theater on Chicago’s North Side, the infamous site where, in 1934, FBI agents gunned down legendary gangster John Dillinger. The exterior of the Biograph was temporarily restored to its gangster-day glory for the filming of the Johnny Depp biopic Public Enemies.

Mount Carmel Catholic Cemetery

- Mount Carmel Catholic Cemetery is the final resting place of the most notorious of Chicago gangsters, Al Capone. The cemetery just outside Chicago honors the graves of other Chicago gangsters like Sam Giancana, "Deany" O’Banion, and the "Terrible" Genna brothers.

Valentine’s Day Massacre Site

- On February 14, 1929, seven gangsters were shot and killed at a garage in Chicago’s Lincoln Park neighborhood in what is known as the "Saint Valentine’s Day Massacre." It is believed that the murderers where members of Al Capone’s gang dressed as police officers. The main target, "Bugs" Moran, escaped injury. If you love gangster lore, this Chicago site offers an "I was there" moment.

Union Station

- Chicago’s Union Station is the known-site of the famous shootout scene in the movie The Untouchables. While the film’s “baby carriage" scene was created by Hollywood, Chicago gangster fact and fiction are so blurred that it’s now a stopping point on many Chicago gangster history tours.

Untouchables Tours

- If you’re hot for Chicago gangster history, Untouchable Tours are billed as "Chicago’s Original Gangster Tour." Take the 2-hour driving tour in a jet black school bus to Chicago gangster landmarks and hangouts, including the Biograph Theater, Dion O’Bannion’s flower shop, Holy Name Cathedral, and site of the St. Valentine’s Day Massacre. Tour guides wear gangster garb and get into the lingo. Tours leave from 600 N. Clark Street.

Tommy Gun’s Garage

- For a lighthearted look at Chicago’s gangster past, visit Tommy Gun’s Garage, an audience interactive dinner theater decorated as a 1920s speakeasy. Tommy Gun’s Garage recreates the ear of Chicago gangsters with a sit-down dinner and musical comedy revue with gangsters and flappers performing tunes from composers like George Gershwin and Cole Porter. Tickets are $60 – $70 per person.


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Avenue Crowne Plaza Hotel and Suites Chicago Downtown - 160 E Huron, Chicago, Illinois, 60611 Avenue Crowne Plaza Chicago Magnificent Mile - Chicago, Illinois (IL)
160 E Huron, Chicago, Illinois, 60611
Contact: 312-787-2900 Fax: 312-787-6093
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