This Legendary Chicago Bar Frequented By Al Capone Still Serves Up Plenty Of Mob History

While a notorious criminal like Al Capone isn't necessarily someone to admire, he's certainly a fascinating figure surrounded by a lot of intriguing history. Capone was one of the leaders of the Chicago organized crime scene from 1925 to 1931, and his gang is believed to have made around $100 million through their illegal operations. Unconfirmed lore abounds, too — was he indeed behind the infamous St. Valentine's Day Massacre in 1929, for example? To dive into Al Capone history is to explore the history of the United States during the Prohibition and the resulting rise of organized crime. And if you can get that education in while enjoying a classic cocktail, that sounds like a pretty sweet deal, doesn't it?

At the Green Mill Cocktail Lounge in Chicago, you can literally experience the kind of place Capone would hold court — because this was one of his favorite joints. You can even sit in what was once his private booth. What's interesting to note is that, from there, you can clock every entrance into the bar, which a mob boss with lots of deadly competition would want to have eyes on at all times. The Green Mill is up there with the oldest pubs in the U.S. worth visiting: It opened as Pop Morse's Roadhouse in 1907 and became Green Mill Gardens in 1910. Allegedly, one of Capone's righthand guys, Jack "Machine Gun" McGurn, was a part owner of Green Mill while it was a speakeasy during the Prohibition.

McGurn supposedly helped keep that private booth cordoned off for his employer, and with his aid, Capone's operation could run illicit booze through tunnels and serve it at the bar. On top of all that mob and specific Capone history, though, the Green Mill is also a star on the country's jazz map. Legends such as Al Jolson and Billie Holiday performed there. To tie together the mob and jazz legacy, it's alleged that McGurn may have attempted to murder singer Joseph Lewis when the performer thought of entertaining at a rival venue. In fact, the Frank Sinatra movie "The Joker Is Wild" is based on the tale. But times change, and the Green Mill had a rough few decades in the middle of the 20th century. 

Post-Prohibition, different owners came and went. But in 1986, Dave Jemilo purchased it and restored it to its former glory complete with regular jazz performances that still draw a crowd to this day — come for the Capone history, stay for the excellent music. While it might not be one of the best cocktail bars in the country, you can enjoy a mean martini or classic lager there. The bar keeps things low-key, with its website stating that bartenders will not make a mojito or "drinks with egg whites," and that they're cash only. Stop by for a well-made, straightforward beverage with some history and music, and if you're in search of more mafia lore, check out Bamonte's, Brooklyn's oldest Italian restaurant with mob ties.