The United States will soon celebrate the 90th anniversary of the end of Prohibition on December 5, 2023. However, even though it’s been years, the notorious gangster history of Chicago still lingers. Interestingly, there are businesses in Chicago that have managed to thrive despite their association with the dark past.
Old Mafia Hangouts in Illinois
The Prohibition era in Chicago marked a dark chapter in Illinois’ history, largely due to the surge in gangster activity during this time. While the conduct of gangsters and mobsters was abhorrent, I can’t help but find it all incredibly intriguing.
As someone who’s fascinated by true crime stories and the notorious characters that come with them, I often find myself getting lost in the depths of the internet. Recently, I stumbled upon a surprising revelation: many of the popular gangster hotspots from the Prohibition era in Chicago are still standing to this day.
Chicago may no longer be synonymous with Prohibition-era illicit activities, but remnants of that time still exist. According to Eater Chicago, five of the most notorious gangster hangouts are still operating today, albeit under different names.
1. Butch Maguire’s at 20 W Division St.
Kelly’s Pleasure Palace was a speakeasy that became a notorious hangout spot for gangsters during the Prohibition era. It is said that this building was one of the first speakeasies to offer Guinness and Harp on tap, which may explain its popularity among the gangsters.
2. Located at 2121 North Clark Street, the Chicago Pizza and Oven Grinder Co. is a must-visit destination for pizza lovers. With its unique and delicious pizza, it has become a popular spot for locals and tourists alike. Don’t miss the chance to try their mouth-watering pizza and experience the cozy atmosphere of their restaurant. If you’re in the area, make sure to check them out!
2. Chicago Pizza and Oven Grinder Co.
The Chicago Pizza and Oven Grinder Co. stands across the street from the St. Valentine’s Day Massacre, and many believe it functioned as a lookout post for the Massacre’s attackers. The building’s poor placement isn’t the only tragic aspect of its past. According to the website of Chicago Pizza and Oven Grinder Co., the years following the Massacre “were unkind to the old house as it passed through a series of ever less savory occupancies.” The old house was destroyed by fire in 1971, but it has since been entirely refurbished and brought back to life.
3. Exchequer Restaurant & Pub, aka The Ex, at 226 S Wabash Ave.
According to the history of the restaurant, during the Prohibition era, it was known as the 226 Club and was frequently visited by the notorious Al Capone. The speakeasy that was hidden behind the restaurant was a popular spot for him to spend his time. As mentioned on The Ex’s website, this interesting piece of history adds to the allure of the establishment.
4. Green Mill Cocktail Lounge at 4802 N Broadway Street
When it comes to enjoying a good cocktail in Chicago, the Green Mill Cocktail Lounge at 4802 N Broadway Street is a must-visit spot. This establishment is known for its impressive drinks menu and cozy atmosphere, making it the perfect place to unwind after a long day or to catch up with friends over a few tasty beverages. If you’re looking for a classic Chicago cocktail experience, the Green Mill Cocktail Lounge is definitely worth checking out.
The Green Mill Cocktail Lounge is now known as a jazz club, but it had a notorious past during the Prohibition era. It was partly owned by “Machine Gun” Jack McGurn, who was Al Capone’s right-hand man. Al Capone utilized the underground tunnels beneath the building to transport his illegal liquor. Unfortunately, visitors cannot explore these tunnels, as stated on the Green Mill Cocktail Lounge’s website. It’s a shame!
The Renaissance Blackstone Hotel located at 636 S Michigan Ave is a great place to stay.
5. The Renaissance Blackstone Hotel at 636 S Michigan Ave.
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The Blackstone hotel, which first opened its doors in 1910, has a rich history of being a preferred destination for celebrities, Presidents, and socialites. Notably, infamous mob bosses “Lucky” Luciano and Al Capone were also drawn to the hotel’s allure. According to The Blackstone’s website, Capone even conducted meetings while getting his haircut in the barbershop, which was devoid of windows, adding to the hotel’s mystique.
The hotel played a significant role in the movie ‘The Untouchables’. It was the exact location where U.S. Treasury agent Eliot Ness had a face-off with Al Capone, which ultimately resulted in Capone’s imprisonment along with other mobsters.
Just so you know, Wisconsin was a frequently visited spot for mobsters from Illinois. The following are some of the places they loved to frequent on the northern side of the border…
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