From Frank Sinatra To Al Capone, This Chicago Jazz Club Is Filled With History (And Secrets)

If you've ever seen the musical "Chicago" or the 2002 film adaptation, you know that jazz clubs in the Windy City have a long, colorful, and sometimes shady history. While many of the establishments that thrived in Prohibition-era Chicago are long gone, one of them, the Green Mill, is not only still open but also has secrets to share. This cocktail bar and jazz club, officially named the Green Mill Cocktail Lounge, has been a place for everyone from musicians to mobsters to drink, dance, and be merry for over a century.

The Green Mill actually predates both Prohibition and the First World War, having opened its doors in 1907. At the time, it was called Pop Morse's Roadhouse, and it catered to mourners wanting to raise a toast after visiting one of two nearby cemeteries. This slightly morbid association would continue throughout the Green Mill's history, as it became a favorite hangout for Chicago gangsters, including Al Capone, who took over the lounge during Prohibition and was said to have used tunnels underneath it for his bootlegging operations. The Green Mill was also beloved by entertainers, including Charlie Chaplin and Frank Sinatra.

Happily, today the Green Mill is known less for gangsters than it is for good cocktails and live jazz. There are still some decidedly old-school touches to a night at the Green Mill, though. For one thing, the lounge is cash only, so before you head there, check the night's cover charge and hit up an ATM.

For another, the Green Mill is firm that there are two kinds of cocktails bartenders will not serve: drinks made with egg whites and mojitos. The club sadly doesn't offer tours of the famous bootlegger tunnels — a question the Green Mill staff gets so regularly that it's on the FAQ page of the club's website.

As for what is on the menu at the Green Mill, there's a lot to enjoy, in terms of both music and drinks. A look at the Green Mill calendar shows live jazz every night of the week, sometimes with multiple shows per day. While you're listening, you can enjoy a draft beer or a classic cocktail, like Frank Sinatra's very specific martini. The Green Mill doesn't serve food, but it is located in a neighborhood with plenty of restaurant options. Remembering that, you can always find a place to sample some Chicago deep dish pizza or a local spot for a classic Chicago hot dog before heading to the club.