Story: Can You Keep a Secret? Revisiting Chicago Speakeasies

Cara Van

By Cara Van
Written on 26 April 2013

America has an enduring fascination with Al Capone, the mob, gangsters and bootlegging. A visit to Chicago is a great opportunity to immerse yourself in this fascinating history and culture.

Prohibition-era Chicago is one of the most evocative periods of time in American nightlife. Even now, nearly 100 years later, our culture remains fascinated with secrecy, alcohol and mobsters. The prohibition days in Chicago have been depicted in countless films, television shows and other works of fiction, and America has had an enduring fascination with Al Capone, the mob, gangsters and bootlegging. A visit to Chicago is a great opportunity to immerse yourself in this fascinating history and culture.

Even though alcohol was illegal during the Prohibition, Chicago residents refused to let the party end. They kept the booze flowing into the town through illegal speakeasies, which were hidden in plain sight in almost every neighborhood. These bars were disguised as back rooms, soda shops and basements.

A few of the famous speakeasies of Chicago are still open today and you can likely find tours in Chicago that will reveal the history behind these establishments. John Barleycorn in Lincoln Park was disguised as a Chinese laundry and barrels of booze were smuggled inside under dirty sheets. Another secret drinking establishment, Marge’s Still, brewed gin upstairs in a bathtub.

One of the most famous speakeasies was Room 21, which is where famous gangster Al Capone had his largest brewery and speakeasy when he was at the height of his influence in Chicago. It even has a secret hallway and staircase that leads to a street exit.

Legends and myths abound about these old-fashioned clandestine drinking establishments and the shady characters that frequented them. Visiting one of the existing speakeasies is certainly a must when in Chicago.

Speakeasies That Still Exist in Chicago

Although many of the Chicago speakeasies closed their doors when prohibition ended, a few remained open and have been serving up drinks ever since. There are a number of these historic Chicago drinking establishments that you can visit during your stay in the city.

The Green Door Tavern

The Green Door Tavern on Huron was named after its unmarked green door which was a secret side entrance. In fact, the term “green door” was a common euphemism for a speakeasy at that time. The alcohol at this speakeasy was supplied by the notorious North Side Gang, led by Irish-American bootlegger and mobster Dean O’Banion. Of course, this meant that the Green Door would have been the enemy of the even more notorious Al Capone.

The joint is still open today and serves up excellent cocktails and delicious food. Try the corned beef sandwich and sip on a Moscow Mule which is a refreshing mixture of ginger beer, lime juice and Russian vodka.

The Green Mill

Originally known as Pop Morse’s Roadhouse, this business opened in 1907 and was later named Green Mill Gardens. The Green Mill was inspired by the Moulin Rouge in Paris and it was a massive pleasure paradise with dancing girls, fountains and much more. Even its name was a tribute to the “Red Mill” of the Moulin Rouge.
During the Prohibition Era, Jack McGurn, who was part of Al Capone’s outfit, became a part-time owner. It is said that there is a network of tunnels leading out underneath the Green Mill that were used by gangsters to get around in secrecy. After prohibition was over, the Green Mill became somewhat of a more respectable place to drink and started to attract many popular jazz acts. It is now home to the popular Uptown Poetry Slam. It has also been a setting in many films, including “Next of Kin,” “Prelude to a Kiss,” “Soul Food” and “High Fidelity.”

Simon’s Tavern

Back in the 1920s a Swedish immigrant named Simon Sumberg opened up a cafe, which quickly became a speakeasy. This tavern was supplied with booze by Al Capone and his men, and Simon sold whiskey out of the tiny room downstairs. These days, you can ask Scott, the current owner, about the story and he just might take you downstairs and reveal the entire history to you.

While you are there, be sure to sample of some of the delicious Swedish-inspired drinks including the traditional Scandinavian spiced wine.

These are just a few of the famous Chicago speakeasies that still remain open to this day, where you can enjoy a drink and some great stories about the shady secrets and larger-than-life characters of Chicago’s past.

About the Author: Kayla Waters is a Chicago resident who frequently attends the poetry slam at the Green Mill before finishing off the night with cocktails at Simon’s Tavern.


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