Al Capone would sit at the lush green booth because he could monitor both entrances while enjoying the show.
The Green Mill Cocktail Lounge has hosted some of Chicago’s best Jazz performers for over a century. During Prohibition, the lounge was a notorious speakeasy run by “Machine Gun” Jack McGurn, a known associate of Al Capone. Today, the Green Mill continues to play Jazz all night, seven nights a week.
Walking into the Green Mill Cocktail Lounge is like taking a step back to the 1920s. Jazz and Blues play hard and loud all week with multiple bands per night. Many patrons dress in clothes from the era and swing dance steps away from the band stage. The nightclub hosts a number of bands, poetry slams, and jam sessions that often last until 4 or 5 a.m.! Check the calendar on the lounge’s website to see whose playing each night.
The iconic lounge has a long history in Chicago. Located in Uptown, the original Green Mill was much larger than it is now, taking up the entire red brick building. The Green Mill Gardens, as it was once called, had a full ballroom, a restaurant, and lounges where live music and dancing girls performed every night. Famous musicians like Billie Holiday, Von Freeman, Franz Jackson, and Wilbur Campbell have all played the jazz club.
The cocktail lounge is best known as a former speakeasy and mobster hangout for Italian boss Al Capone. Capone had his own booth that allowed him to enjoy nightly shows while keeping an eye on both entrances. In the case of raids, tunnels beneath the bar lead out to the streets for a quick escape and also served to smuggle alcohol in. While the trap door to the tunnels still exists, you can’t explore them (we asked and they said no.) These days, the Green Mill is smaller (just the lounge) but it’s still as lively as ever.
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The cash-only bar sticks to its traditional roots when it comes to serving drinks. Bartenders serve classic cocktails with masterful execution. They don’t have a cocktail list, so you have to know what you like before ordering. The lounge also doesn’t serve food, but there are several restaurants within walking distance such as Fiesta Mexicana, Demera (Ethiopian), and the Golden House Restaurant and Pancake House.
The Green Mill doesn’t take reservations, only a cover charge of $5-$15 depending on the musical act that night. The lounge is first come, first serve so if you want to get a seat at the famous Al Capone booth, we recommend getting there early. If you’re not able to snag that historic seat, you can still enjoy a piece of Chicago history hosting the future of Jazz music.
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This is also a great place to welcome the 20s back on New Year’s Eve. Dress up in your best flapper dress and head to Uptown Dec 31. The Green Mill will host a Battle of the Saxes and a Late Night NYE Jazz Jam to celebrate 2020.
Feature Photo: @kenzirkel