Make New Friends, But Keep the Old

By Michelle Moore

Prohibition Era Chicago brings to mind images of gangsters and flappers sequestered away in smoky speakeasies, clandestine clubs overflowing with jazz and gin. Many former speakeasies such as the infamous Green Mill and The Rainbo Club are still open for business, enabling patrons to step (or shimmy) back to the roaring 20’s for a taste of the same Sazerac Al Capone once swilled.  However, recent years have given rise to a new generation of bars and cocktail lounges, built upon the backs of bootleggers, serving up highball glasses of swirling intoxicants at once familiar and entirely new. These fanciful, reimagined beverages have refined the spirit of the very spirits at hand, while paying homage to the raw and gritty Prohibition Era libations from whence they came. Sidle over to these fine Chicago establishments to ring in the new year with a taste of the old. One is silver and the other’s gold!

The Drawing Room

The Drawing Room in Chicago

A discretely marked door tucked between two storefronts in Chicago’s bustling Gold Coast is the only whisper passersby may receive of the epicurean wonderland unfolding beneath their feet.  Descending the foreboding stairs to the cavernous dining room below, visitors to The Drawing Room can’t help but suspect they’ve slipped through a portal to 1920’s Chicago.

With mixologist Charles Joly manning the martini shakers, it’s no wonder The Drawing Room has been consistently featured on Esquire’s “America’s Best Bars” list since its inception in 2007. Joly’s discerning fingerprints are all over The Drawing Room’s well-appointed bar, stocked with a litany of local labels produced in and around Chicago. Malort,  anyone? Patrons who settle at the low, stone tables in the dining room, away from the main bar, will find their drinks mixed tableside by deftly skilled servers pushing gilded beverage trollies. The highlight of my visit was The Affiliate, a Charles Joly original featuring 8 year-old Jamaican rum, fino sherry, and Angostura bitters, sure to chase the chill from your bones even as the snow piles up outside.

Come for the cocktails, stay for the club. The Drawing Room gives way to Le Passage, an upscale nightclub churning out tunes faster than the kitchen churns out kobe beef sliders. chatting up your server may grant you access to the dance floor without paying the inordinate cover charge…but you didn’t hear it from us! 




Barrelhouse Flat

If Roald Dahl’s Willie Wonka sought to sip crafted cocktails and rub elbows with Chicago’s hippest hipsters, this new Lincoln Park haunt would undoubtedly be his first stop. With wispy clouds of homemade cotton candy gracing the tables and glistening decanters of punch drained into tea cups, The Barrelhouse Flat infuses an enchanting sense of whimsy into a laid-back night on the town.

A complex cocktail menu 60 selections deep, lovingly crafted by mixologist Stephen Cole, promises not to disappoint even the most particular palates. Can’t find what you like? The friendly, attentive staff are incredibly knowledgeable (and in my case, mercifully tolerant) and the bartenders would be happy to whip up something special to suit your personal taste.  I found their rendition of The Last Word (my favorite Prohibition Era cocktail, originating in Detroit in 1922) to be top notch.  

While the downstairs bar is a hectic, seat-yourself affair, the lavish upstairs lounge, complete with private billiards room, is where the magic happens. One part speakeasy, one part cozy living room, it’s worth arriving early to secure a seat near the fireplace.



Curio ChicagoWell-informed Chicagoans putting on the ritz this Saturday night need look no further than Curio… if they can find it! Nestled cozily beneath Gilt Bar, Curio is neigh inaccessible to all but those who already know where it is. Take the staircase behind the bar, follow the cryptic signs, spin around three times (optional, although I’ve heard it helps) and duck through the heavy curtain to find yourself in a candlelit chamber of classic cocktails and whispers in the dark.

If you’re not fortunate enough to secure one of the three (just three!) coveted barstools, don’t fret. Massive red leather sofas will cradle you in comfort while the waitstaff mixes your Manhattan. The cocktails here have a classic flair. Skip the somewhat tawdry tiki-inspired menu and let the bartenders do what they do best. The Sidecar, Whiskey Sour and Pimms Cup all exceeded my lofty expectations.

A word of warning: the bar here is cash only. A hassel? Yes. But worth the minor inconvenience to preserve the hushed, underground vibe. Apparently the old-fashion cash register prominently displayed behind the bar isn’t just for show!

Interested in exploring the authentic side of Prohibition Era Chicago? The Chicago Historical Society hosts a plethora of pub crawls where history buffs and curious cocktail aficionados alike can brush up on their Chicago lore.

Curio Cash Register in Chicago