C is for Cocktail Guest Post: 7 of Chicago’s Most Famous Speakeasies (Which Are Still Open Today!)

Looking for a sip of Chicago history? Then check out this lovely guest post from Liana Camen, the Mayor of Drinxville, about Chicago’s historic Prohibition bars!


Although Chicago doesn’t have the centuries of history that eastern seaboard cities like Philadelphia, Boston, and New York do, the Windy City’s role in early commodities trading, mechanized industrialization and U.S. gangster culture has made it a historical mecca for travelers fascinated by the early 1900s. The passage of the eighteenth amendment in 1920, and the nationwide prohibition on alcohol that the amendment created and enforced, turned Chicago into a city of violent gangs, irrepressible good times, and seemingly limitless rivers of illicit booze.

These illegal spirits were bought and sold by establishments called speakeasies, which were secret bars and pubs that operated outside the purview of the law – often by bribing public officials and convincing cops to look the other way. Today, even though Prohibition is a distant memory, Chicago’s speakeasy culture hasn’t completely disappeared. Here are seven modern-day watering holes that have either been continuously operational since the 1920s or are striving to keep the proud speakeasy tradition alive in midwestern America’s biggest metropolis.

~ T H E   B A R S ~


The trademark glowing sign of the Green Mill, Chicago’s most well-known Prohibition Era bar. Photo Source: this article at the Chicago Reader; Photographer Richard A. Chapman


  1. The Green Mill (4802 North Broadway Avenue – www.greenmilljazz.com)


An interior shot of the Green Mill, featuring the the booth that Al Capone favored in the foreground. Photo Source: Photographer Tom Gill, from this article at savingplaces.org

Supposedly, this venerable establishment was created in the 1920s as an homage to the celebrated Red Mill bar in Paris, France (the setting of Baz Luhrman’s film Moulin Rouge). Formerly owned by Jack McGurn, who was an associate of Al Capone renowned for his violent nature and ruthlessness with a machine gun, the Green Mill was the picture of opulence in the pre-Prohibition period. After the eighteenth amendment’s passage, the bar downsized and served Chicago’s finest and most infamous alike. Visitors to Chicago today can go and enjoy (legal) spirits inspired by those crafted by Prohibition-era bartenders while listening to the best that Chicago’s vibrant jazz scene has to offer. No secret password to come into the Green Mill anymore – simply walk up to the bar and order a drink!


  1. The Zebra Lounge (1220 North State Parkway – www.thezebralounge.net)


The darkened interior of the Zebra Lounge, complete with zebra lamps. Photo Source: The Chicago Reader

The Zebra Lounge feels like a relic from an age long gone that somehow ended up down the block from steel skyscrapers and multinational conglomerate headquarters. Operational since 1929, the lounge actually owns the third-oldest liquor license in Chicago, which is quite the accomplishment in that city of ancient bars and pubs. The bar is located inside the Canterbury Courts apartment complex, and would-be patrons must pass under a set of black arches in order to access the tiny establishment. Known in the neighborhood for its commitment to being an authentic, old-fashioned piano bar, the Zebra Lounge hosts live piano players seven nights a week. If you find yourself in Chicago and in the mood for some Elton John or Billy Joel, you can’t do any better than a visit to the Zebra Lounge.


  1. Simon’s Tavern (5210 N Clark St)

simon bar sign.jpg

The cheery glowing sign of Simon’s Tavern. Photo Source: getawayhostel.com

Simon’s Tavern is another longstanding Chicago neighborhood tradition. Founded as a cafe by a Swedish immigrant in 1929, the owners of the tavern quickly acquired a new set of revenue streams by rebranding as a speakeasy, bottler and distributor of illegal spirits. The whiskey distributors operating out of the bar’s basement were rumored to be supplied by Al Capone himself, and the Capone organization reportedly had a fondness for the Swedish drinks and bar food supplied by the tavern’s immigrant chefs. In the new millennium, the owners of Simon’s have attempted to stay true to the bar’s origins: the tavern sells huge quantities of glogg, which is a traditional Swedish spiced wine that is only brewed during the Christian holiday season. House drinks also include copious amounts of Swedish liquors, making Simon’s Tavern a can’t-miss stop on any speakeasy tour through the city.


  1. Room 13 (3222 N. Sheffield Ave – www.oldchicagoinn.com/rooms/room13.shtml)


The public entrance to Room 13. Photo Source: Thrillist

When people think about “secret” bars in Chicago, nearly everyone brings up Room 13. Although the bar has no tangible connection to the Prohibition era in Chicago, its entire ethos hearkens back to the 1920s in every way. Located deep in the bowels of the Old Chicago Inn, Room 13 requires visitors to either book a room in the hotel or supply a secret password to enter. The bartenders are highly trained in the art of the cocktail, and they supply guests with expertly crafted Old Fashioneds and Manhattans while expounding upon the intertwined history of speakeasies, jazz and old metropolises. Even the décor of the bar is set up to perfectly mirror the embellishments and gaslight sensibilities of authentic speakeasies in and around the city. Certainly an interesting – and intoxicating – attraction in the heart of Chicago.


  1. The Office (955 W Fulton Market)


A comfortable nook at The Office. Photo Source: Bach Ha/Grant Achatz at Flickr

Located beneath a trendy restaurant called The Aviary, the Office is the perfect complement to an opulent dining experience – if you know the secret number to text for reservations. That’s right – having a drink at the Office depends on either receiving an invitation from the wait staff to descend into the basement for an after-dinner digestif, or knowing the well-guarded, exclusive reservation digits. Open since 2011, the Office charges a pretty penny for its libations, but each drink is crafted with care by licensed mixologists using equipment such as a rotary evaporator. A must-see location for people who spare no expense to quench their thirst for innovative drinking experiences.


  1. The Green Door Tavern (678 North Orleans – www.greendoorchicago.com)


Inside The Green Door Tavern. Photo Source: Spring Rewards

The Green Door Tavern claims to have had its doors open since 1921, but the origins of the building that it is housed in actually stretch back even further. The squat, two story wooden structure was built directly after the Great Fire of 1871, which makes it one of the only wooden buildings left in Chicago that was constructed before the Central Business District fire code ordinance banning wood buildings was passed in 1873. In 1921, an Italian immigrant opened a small speakeasy that signified its presence in the neighborhood by painting its nondescript door green, and a Chicago tradition was born. The establishment maintains many of the old bar’s distinctive traits today: it is known throughout the city for its cheap drinks, expansive bar menu and casual atmosphere. Certainly worth passing through for a drink or two!


  1. The Berghoff (17 West Adams Street – www.berghoff.com)


That famous sign! Photo Source: Tripadvisor

The Berghoff is the proud holder of the first liquor license issued in Chicago after the repeal of Prohibition in 1933, and its tumultuous history goes back decades before that moment. The bar was founded in 1898, and was actually able to remain open for business during Prohibition by playing by the rules (sort of.) The Berghoff became famous for selling “near beer” products, which were typically low-alcohol content malt beverages that remained beneath the government’s official alcohol threshold while still supplying patrons with plenty of good times. Today, the bar is actually still owned and operated by the original Berghoff family. Patrons can visit the pub for a dining experience steeped in the sordid history of the neighborhood and city and for a taste of Berghoff’s famous root beer – the recipe goes back four generations, and the beverage is nearly as famous as the bar itself!


Chicago is a city full of fascinating drinking and dining experiences, many of which stem from an era that peaked and passed almost one hundred years ago. A visit to this majestic city of the shores of Lake Michigan simply is not complete without a trip to each of these seven venerable establishments!


This guest post comes from Liana Camen, who balances her time between her family, her freelance writing career, and fulfilling her duties as Mayor of Drinxville. She enjoys experimenting in the kitchen, traveling to exotic places, and sipping on a nice stiff drink.


About lupachi1927

My name's Megan, and I'm a writer with an interest in history. While I might not be a real historian, I'm a very thorough researcher. This blog is my place to post about all the interesting historical tidbits I find that can't use in the novel I'm working on, which takes place in Chicago in 1927. If you're looking for research help, writing feedback, or just want to say hi, feel free to drop me a line! :)
This entry was posted in C is for Cocktail series, guest post and tagged . Bookmark the permalink.

3 Responses to C is for Cocktail Guest Post: 7 of Chicago’s Most Famous Speakeasies (Which Are Still Open Today!)

  1. The Green Mill and The Office…I want to drink there!


    • lupachi1927 says:

      Me too! I’ve never been to either. Only been to the Berghoff, but that was pretty neat. I’d love to try Room 13 too. The secret entrance looks really cool! Have you been to any on the list?


  2. jazzfeathers says:

    Fantastic post. Thanks so much for sharing the history of these places 🙂


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