Explore Chicago’s Infamous Gangster History Tours

The fascination with Chicago’s infamous gangsters continues today, despite the height of gangster culture occurring long before World War II. Here are some ways to immerse yourself in the world of legendary figures like Al Capone and John Dillinger with various gangster tours in Chicago.

Biograph Theatre

The Biograph Theater, located on Lincoln Avenue in Chicago’s North Side, is famously known as the site where, in 1934, FBI agents awaited gangster and bank robber John Dillinger. Dillinger was shot while exiting a movie—appropriate for a gangster movie—as he attempted to draw a weapon on the agents. Today, the theater houses the Victory Gardens Theater, and its exterior was restored for the filming of the Johnny Depp biopic Public Enemies.

• Address: 2433 N. Lincoln Ave.

Mount Carmel Catholic Cemetery

Mount Carmel Catholic Cemetery serves as the final resting place for many notorious Chicago gangsters, including the infamous Al Capone. Located just outside Chicago in Hillside, this cemetery also contains graves of other well-known gangsters from the era, such as “Deany” O’Banion and the “Terrible” Genna brothers.

• Address: 1400 S. Wolf Rd., Hillside, Ill.
• Office Hours: Monday through Friday, 8:30 a.m.-4 p.m.; Saturday, 9 a.m.-1 p.m.

Tommy Gun’s Garage

Located in Chicago, Tommy Gun’s Garage is an interactive dinner theater that brings to life the Prohibition-era. This venue, styled as a 1920s “speakeasy,” features a delicious sit-down dinner alongside a lively musical show with “gangsters” and “flappers,” performing songs from famous composers of the time, including George Gershwin and Cole Porter. Though the entertainment is cheesy, it creates a fun atmosphere if you can relax and enjoy the experience.

• Address: 2114 S. Wabash Ave.
• Phone: 312-225-0273
• Tickets: $60 – $70 per person

Chicago Union Station

Chicago Union Station is not only a vital hub for Metra and Amtrak but is also a significant site for gangster lore, due to its notable representation in the film The Untouchables. The dramatic shootout scene is entirely fictionalized, yet the intersection of fact and fiction regarding Chicago gangsters makes this location compelling for enthusiasts of gangster history.

• Address: Canal Street between Adams and Jackson

Valentine’s Day Massacre Site

On February 14, 1929, the notorious St. Valentine’s Day Massacre occurred when seven gangsters were killed at a garage in Chicago’s Lincoln Park neighborhood. Though unproven, it is widely believed that the murders were orchestrated by members of Al Capone’s gang or hitmen contracted by Capone. The attackers deceived their targets by masquerading as police officers. Notably, the intended target, “Bugs” Moran, escaped unharmed due to an early signal that alerted the killers before Moran arrived at the scene. Unfortunately, while visiting the historical site may offer a sense of the past, the original building is long gone.

• Address: 2122 N. Clark St.

Chicago Untouchable Tours

If guided experiences appeal to you, consider joining Untouchable Tours, advertised as “Chicago’s Original Gangster Tour.” This two-hour driving tour, conducted in a jet black school bus, guides you through numerous gangster landmarks and hotspots. The costumes worn by tour guides add to the immersion as they embrace the characters and slang of the era.

• Address: Tours depart from 600 N. Clark St.
• Reservations: 773-881-1195
• Price: $30 per adult
• Hours: Tours operate various times seven days a week.