Chicago Bars with a Speakeasy Past

For better or worse, many people associate Chicago with its gangster-filled past. Perhaps it’s tough to forget Al Capone and bootlegging because relics of that time are still around. On December 5th, 1933, The Man repealed Prohibition, and the country’s ban on alcohol was finally lifted after a 13-year drought. The city sighed in relief. No longer forced to function as speakeasies, its under-the-radar watering holes threw off their shrouds of secrecy. Fortunately, many bars from that era still remain, ready for you to explore. Personally, I believe any bar can serve you a cold brew, but only a select few can also serve up an interesting story. Get your fill of both at these historic bars.

Marge's Still

1758 N Sedgwick St, Chicago, IL 60614

Marge’s Still is located in a building that was erected in 1885, so it’s pretty impressive that the bar is still around. A favorite of Old Town residents, this vintage joint boasts a clean, elegant interior and serves up bistro cuisine. However, back in the day, it was pouring gin that was made in a bathtub on the second floor.

Rainbo Club

1150 North Damen Avenue, Chicago, IL, United States

A classic spot located on the border of Wicker Park and Ukrainian Village, Rainbo Club lets no outside light into its dim confines. The boarded-up look came in handy during Prohibition, helping to keep outsiders unaware of the speakeasy goings-on inside. Nelson Algren, Vince Vaughn, Liz Phair, and Jack White have all hung out here.

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Hangge Uppe

14 West Elm Street, Chicago, IL 60610, United States

The Hange Uppe largely attracts a college and hard-partying crowd that’s looking to throw down on the dance floor and throw back one too many drinks. That’s not necessarily a bad thing if you’re in the mood for it. Though Top 40 jams blare throughout, a closer look will reveal that Hange Uppe is actually pretty old. It’s not impossible to imagine it as a downstairs speakeasy back in the earlier 1900s.

Simon's Tavern

5210 N Clark St, Chicago, IL 60640

A charming watering hole located in the Swedish Andersonville ‘hood, Simon’s Tavern used to run a speakeasy out of the basement named the N.N. Club (the “No Name Club”). Today, locals love to stop in during the colder months for some glogg, a Nordic specialty consisting of warm, mulled wine.

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The Hideout

1354 W Wabansia Ave, Chicago, IL 60642

One of the city’s finest “hidden” gems, the Hideout is located on an industrial stretch that’s also home to a garbage-truck parking lot and a municipal-car gas station. The bar is basically a 100-year-old balloon-frame house that serves booze out of its living room, and hosts comedy sets and concerts out of the back. In fact, this is a spot where Jack White has played, Mavis Staples recorded a live album, and Neko Case worked as a bartender. Imagining it as a speakeasy is so easy, one tends to wonder what else goes down here after closing hours.

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Burwood Tap

724 W Wrightwood Ave, Chicago, IL 60614

Most of the crowd here is made up of locals from the fancy Lincoln Park neighborhood and DePaul University students. Nevertheless, Burwood Tap remains a charmingly old-school spot that’s filled with interesting historical knickknacks, such as a Richard J. Daley mayoral-campaign poster. Stop in Monday through Thursday at 8:30 p.m. to hit up the free buffet.

Twin Anchors Restaurant & Tavern

1655 N Sedgwick St, Chicago, IL 60614

Another one of Frank Sinatra’s favorite spots, Twin Anchors is largely known today for its tasty ribs and its cameo in The Dark Knight. Regardless of whether you’re eating or not, it’s still a great spot to enjoy a drink and the charming nautical theme. A secret escape door still remains in the southwest corner of the bar to this day.

Green Door Tavern

678 N Orleans St, Chicago, IL 60654

In addition to formerly being a speakeasy, the Green Door Tavern has also functioned as a grocery store and Italian restaurant over the years. It’s one of the first buildings erected after Great Chicago Fire of 1871, and it really shows. Its wooden frame leans dramatically to the right, which you can easily spot from across the street.

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Green Mill Cocktail Lounge

4802 N Broadway St, Chicago, IL 60640

The crown jewel of historic-Chicago bars, this classic spot has been around under its current name since 1910. It’s hosted the likes of Frank Sinatra and Charlie Chaplin, and today continues to attract talented jazz musicians who keep the music blaring way past midnight. You can tell that people here care about the music, because the conversations are generally kept to a hushed tone. Patrons also keep coming back for poetry-slam events and a popular Thursday-night swing-dance shindig.

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Southport Lanes & Billiards

3325 N Southport Ave, Chicago, IL 60657

Not only was Southport Lanes a speakeasy back in the day, it also had a brothel upstairs to really ratchet up the illegitimacy. Supposedly, Mayor Cermak used to host poker games in one of the bar’s secret rooms. Today, it also doubles as a bowling alley, and really retains its old-school vibe by hiring real-life pinsetters to keep games rolling along.

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810 W Diversey Pkwy, Chicago, IL 60614

Judging from the party-hard crowd and remodeled look, it’s hard to tell that Durkin’s used to be a functioning speakeasy back in the day. The oddly huge back room was actually where Prohibition Willy’s Speakeasy served up drinks, while a soda shop provided cover up front. Supposedly the owners found a secret room loaded with scotch and brandy when they were remodeling Durkin’s in 1974.

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Schaller's Pump

3714 South Halsted Street, Chicago, IL

The oldest continually-running bar in Chicago, Schaller’s Pump is also a haven for the White Sox faithful and local politicians—a crowd that’s oftentimes one and the same, since the local democratic office is located across the street. During Prohibition, an illicit next-door brewery pumped booze into the bar through underground piping, giving weight to the joint’s name. Stop in before a baseball game to enjoy some hearty eats and live music.

Last updated at Jun 07, 2014