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Best Speakeasy Bars In Chicago

At one point, there were more speakeasies in Chicago than there are bars in the city today. A speakeasy could pop up anywhere from a back yard, basement or a portion of a store. They had some common threads, the basic of which was their secrecy. Often there was a password to get in spoken in hushed tones hence the term speakeasy. Secret drinking joints are really a relic of Prohibition but there are a few spots, subterranean and a little hard to locate, that can take you back to the day.

Harry's Velvet Room
(Photo Credit:Harry's Velvet Room's Facebook)

Harry's Velvet Room
1480 West Webster
Chicago, IL 60614
(773) -868-0608.

The fact that Harry's Velvet Room has been moving locales over the last few decades adds to its speakeasy cachet. It's previous incarnations included its share of whiskey and cigars. This Lincoln Park version of Harry's promises to be more sophisticated and a respite from the hordes crawling around River North every weekend. Staff encourages a no-phone atmosphere while you sip a classic cocktail and swallow briny oysters. The menu is offered late night. The sophisticated vibe is a welcome alternative to a thumping club.

610 North Rush Street
Chicago, IL 60611
(312) 660-7191

JIMMY (at The James) used to be a bit more covert in its operations but it is difficult to be secretive located adjacently to a hotel in River North. JIMMY has a separate marked entrance at Rush Street but accessing the venue through the hidden door and two beads of curtains lends a certain feeling of clout in a town that practically invented the noun. "The street entrance is easy to find, but most guests who have never been before are dazzled by the opulent and cozy décor that makes up the lounge," a spokesperson for the bar said. Order yourself a Rusty Nail, Harvey Wallbanger, glass of bubbles or bourbon to get in the spirit of this speakeasy.

(Photo Credit:

111 W Kinzie St
Chicago, IL 60654
(312) 880-1511

With a precious name, unmarked entrance, below ground space and dimly lit atmosphere, Untitled checks off its necessary speakeasy characteristics. The venue also adds a lovely lighted liquor display including a whiskey "library" with nearly 500 choices, five bar areas for serious drinking and a large dance floor. Swanky food such as bacon wrapped prunes and pig tail arancini compliment the dress code no T-shirts, shorts, sandals or gym shoes.

Double A
108 W Kinzie St
Chicago, IL 60654
(312) 329-9555

Double A squeezes a subterranean into this snug space. You'd never find cocktail concoctions this complicated like vodka, sherry, liqueur, mezcal, barbecue bitters and grapefruit essential oil when Al Capone was alive but they are delicious. The drinks may cost above average, but this 2015 version of a speakeasy won't cost you a night in the slammer.

Southport & Irving (SIP)

4000 N. Southport Ave.
Chicago, Illinois 60613

You probably couldn't rely on bellying up to the bar in your neighborhood speakeasy all week in the 1920s. You can feel the naughty tenor of a secret bar once per week at Southport & Irving during Speakeasy Fridays. Order prohibition-era cocktails, $6 Volstead Act cocktail specials and listen to live jazz from 8 p.m. to 11 p.m. Drinks are drawn from "The Old Waldorf-Astoria Bar Book 1935," a bartender's recipe book of pre-prohibition cocktails popularized post-prohibition at New York's Waldorf-Astoria Hotel. In crafting these cocktails,  Beverage Director, Ardit Dizdari, reproduces drinks according to original recipes using premium and artisanal ingredients circa 2015.


Jacky Runice has been a columnist with the Daily Herald Chicago since grunge music and flannel was the new black. Her fingers and gray matter have been busy as travel editor of Reunions Magazine; penning a column that was syndicated around the nation via Tribune Media Services. Her work can be found at

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