A Prohibition-Era Adventure Through Chicago

Tom Malone/Adventure Tribune
In the 1920s, Chicago became the epicenter for prohibition-era gangsters. Al Capone battled for total control of the bootlegging industry in the Windy City against competitors like Bugs Moran. On February 14th, 1929, gunman massacred seven of Moran’s henchmen; Capone was believed to be behind the attack. The massacre crippled Moran’s operations and gave Capone total control of the city.

After his arrest in 1931, other infamous gangsters arose. John Dillinger, who rose to infamy after becoming “Public Enemy Number One”, was gunned down on the street outside of Chicago’s Biograph Theater, just blocks away from where Moran used to run a speakeasy.
Chicago is steeped in prohibition-era gangster lore. While exploring Chicago, you may find yourself in an old gangster watering hole and not even know it. Here are a few former gangster haunts in the Windy City that you can still spend time in today.

Biograph Theater
John Dillinger earned the title of Public Enemy Number One in 1934 after robbing over 24 banks. On July 22, 1934, he headed to the Biograph Theater with a red-headed date, who dimed him out to the fuzz. When he left the theater, he was shot dead in the street by the F.B.I. The theater still operates as it did in 1934, minus Public Enemy Number One.

Halligan Bar
Formerly owned by Bugs Moran himself, this Irish bar sits at the apex of a triangular street corner. The modern bar has only been in operation since 2001, but the history of the building is worth the stop.

St. Valentine’s Day Massacre Site
In 1929, Al Capone was competing for total control of the bootlegging industry in Chicago against his prime adversary, Bugs Moran. On February 14th, 1929, Capone sent hitmen dressed as cops into Moran’s headquarters and massacred the entire crew, which crippled Moran’s operation. Though the building has since been torn down, the site still remains as a lone grass field. Visit the antique shop next door for some authentic photos of the police investigation.

Chicago Pizza and Oven Grinder
Rumor has it that Capone’s guys waited at this location across the street from Moran’s headquarters to scout the scene before the St. Valentine’s Day Massacre. Nowadays, this restaurant serves this incredible concoction called a “Pizza Pot Pie” that’s just as filling and awesome as it sounds.

Green Door Tavern
During Prohibition, a green door signified a speakeasy’s location. Step into the Green Door Tavern, which has been in operation since 1921, and order an old-fashioned cocktail like Capone’s guys used to.

Renaissance Blackstone
This hotel, built in 1910, served a resting place for notorious gangsters like Al Capone and Bugs Moran. The interior’s ornate finishes haven’t changed since Capone’s day. Step inside and visit the place where Capone used to stay.

Know of any other cool old gangster spots? Let us know by submitting your own article to The Adventure Tribune.


Tom Malone is the Editor-In-Chief of The Adventure Tribune and author of adventure novels, like Across Americana. He is based in Denver, Colorado, where he adventures through the Rocky Mountains while not traveling abroad.
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