Categories: Chicago History

Chicago Gangsters

Author: Molly Ryan

Infamous gangsters such as Al Capone, Bugs Moran and John Torrio made Chicago internationally known for crime, bootlegging, and brothels in the 1920s and beyond. Organizations such as the Chicago Outfit coined the Windy City as its center of operations for organized crime in America.

Today, we can check out the city's gangster history in a variety of ways: Untouchable Tours allows visitors to travel back to the scenes of infamous crimes and learn about the complex inter-workings of Chicago's gang system. For a real speakeasy expereince, Tommy Gun's Garage provides an interactive musical/comedy dinner show that takes visitors back to the days of Prohibition.

History

Gangsters as we now know them sprung up in Chicago in 1920 right after the passing of the 18th Amendment prohibiting the sale of alcohol in the United States. The overwhelming demand for "hootch" led to the formation of groups of gangsters that trafficked illegal alcohol and managed prostitution and gambling rings. The most well-known gang was the Chicago Outfit, which was headed by scandalous gangsters such as "Scarface" Al Capone and Johnny Torrio. On Valentine's Day, 1929, the gang wars in Chicago culminated with the St. Valentine's Day Massacre. Seven members of Bugs Moran's Northside gang (in competition with the Outfit) were found grotesquely gunned down in a garage. Although there was no supporting evidence to accuse Capone of the murders, it is highly suspected that he and his cohort, "Machine Gun" Jack McGurn, were the masterminds behind the slaughter. After Prohibition ended, the groups of gangsters slowly dissolved in Chicago, but there are remnants of these gangs still active today.

Besides being social deviants, Chicago's gangsters were highly active in politics. By interfering with elections, threatening the police, and pulling other illegal maneuvers, gangsters succeeded in influencing the greater Chicago area. The 1920s gangsters will always remain as an important aspect of Chicago's history.

Untouchable Tours

One of the best ways to learn more involved details about the colorful lives of the 1920s Chicago gangsters is to rely on the experts: Untouchable Tours. For $27 you will be led all around the city to old gangster hangouts and shootouts. Upon entry to the black bus (modeled after Capone's black, bullet-proof Cadillac), you will be greeted by well-informed guides dressed in zoot suits, of course. Tap your fingers to the hip blues songs of the 1920s and 1930s while learning about everything from Deanie O'Bannion's passion for flowers to Al Capone's various nicknames. During the drive through many of Chicago's eclectic neighborhoods form the North to the South side, the guides point out and tell the stories of the famous speakeasies, shootouts, and other hot spots frequented by gangsters. Although many of these sights have been remodled, it is still possible to see that  the gangsters have permanetly left their mark around Chicago. The crowd-pleasing and joke-cracking guides keep the bus captivated and the two-hour tour flies by.

The bus tour is conveniently located at the corner of Clark Street and Ohio Street right outside of the two-story Rock N' Roll McDonalds. Unfortunately, there is no sign for the bus, but it pulls up about 20 minutes before the scheduled tour. The black bus decorated with fake gunshots and white lettering is unmistakable. Although it is suggested to make a reservation by calling the Untouchable Tours office, there are usually a few free seats for walk-ons. If you happen to miss the bus or plan on having another adventure before or after the tour, you can shop like a high-class gangster on Magnificent Mile, which is mere steps away from the drop-off location. There are also a slew of esteemed restaurants and some staple chains such as the Hard Rock Cafe and the Rainforest Cafe lining the streets up to Magnificent Mile.

Mount Carmel Catholic Cemetery

For truly motivated 1920s gangster enthusiasts, the Mount Carmel Catholic Cemetery, located in a nearby Chicago suburb, is a must. The cemetery can be found about 25 minutes outside of Chicago in the town of Hillside. Holding more than 400 family mausoleums, the largely Italian cemetery draws visitors from around the world. Gangster legends such as Al Capone, Deanie O'Bannion, Hymie Weiss, "Machine Gun" Jack McGurn, and the Genna brothers along with other big-time criminals are all laid to rest at this historic plot. Besides gangsters, Mount Carmel Catholic Cemetery also holds the graves of the bishops and archbishops of Chicago in the noted Bishops' Mausoleum.

Tommy Gun's Garage

If you feel like being transported back to a "Roaring Twenties" speakeasy, Tommy Gun's Garage is the site to hit up. The interactive dinner theater is packed with gangsters and flappers who serve delicious food and perform in a fun-filled night including live music, dance, and comedy routines. Give the password to the bouncer, try to avoid the coppers, and sip on some quality hootch while enjoying all of the excitement of a wild and crazy decade. This family-friendly downtown joint provides a quality experience for all types and ages.

Check out places of interest near Chicago Gangsters:

Tommy Gun's Garage
2114 S. Wabash, Chicago, IL 60616

The whole family will enjoy this 1920s inspired interactive dinner theater complete with gangsters and flappers. Hidden away in this furtive speakeasy is a musical-comedy troupe that performs the hippest tunes, dances and jokes of the time when Al Capone ruled the streets of Chicagoland.

Untouchable Tours
600 N. Clark St., Chicago, IL 60614

This two-hour guided bus tour of Prohibition-era gangster hot spots is a wild ride.  Visit notorious speakeasies, shoot-out locations and other haunts of the 1920s Chicago gangsters while tour guides provide all of the insider scoop about gangster history. 

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