Once known for its famous gangsters and mob affiliations, Chicago has calmed down noticeably in recent years. Even so, there are still several popular restaurants and bars that have a long history of serving the shadier side of Chicago. These places are all former speakeasies or the site of notable gang activity during the 1900s.
#1: Chicago Pizza and Oven Grinder Co. in Lincoln Park
Famous for its ties to Al Capone’s shooters, this restaurant is a favorite of locals that are looking for a quick bite to eat. This restaurant is located across the street from the famous St. Valentine’s Day Massacre, a 1929 bloodbath that is usually accredited to Al Capone’s gang. Interestingly, this prohibition era murder of several members of George “Bugs” Moran’s gang was never officially linked to Al Capone.
However, the stories say that Al Capone’s men used Chicago Pizza and Oven Grinder Co. as a lookout leading up to and during the massacre of the rival gang members. Because of this, Chicago Pizza and Oven Grinder Co. should be at the top of the list during any tour of Chicago’s old gang hangouts.
Gangster Spot #2: Butch McGuire’s
Formerly known as Kelly’s Pleasure Palace, this bar was a favorite stop for gangsters during the early days of prohibition. It has a long, fascinating history, changing from a tiny restaurant to a speakeasy and then to a mainstream bar. Today, it is known for its selection of beers, including its early adoption of Irish brews such as Guinness and Harp.
Gangster Spot #3: Exchequer Restaurant & Pub
In the early to mid 1900s, this restaurant was not yet named Exchequer. Instead, it was called the 226 Club. This is widely known as one of Al Capone’s favorite hangouts during his reign over Chicago’s streets. It was well equipped for illegal operations, with 2 hidden tunnels that could be used to escape if things went south. Between the illegal booze, the brothel set up in the back, and the rival gangs prowling the street, it was probably wise for Capone to prepare for the worst.
#4: Fox’s Restaurant & Pub
While this one is not directly gang related, this storefront was operated by Al Capone’s sister. If you want to walk in the footsteps of Chicago’s old school gangsters, stopping by this former deli is a quick way to experience a little piece of Chicago’s history.
#5: Green Door Tavern in Uptown
During prohibition, a green painted door usually signalled the presence of a speakeasy and this was no exception. Built in 1871, just after the Great Chicago Fire, the Green Door Tavern was a favorite spot of Dean O’Banion, one of Al Capone’s biggest rivals. Even today, visitors can see the large bookshelf that conceals a hidden passage and visit a modern day speakeasy: The Drifter.
Whether you are a long time Chicago resident or you are just visiting for the weekend, stopping by one of these famous spots is a great way to step into the shoes of one of Chicago’s prohibition era gangsters.