Hidden within the Old Chicago Inn, a secret speakeasy will mix you Prohibition-era cocktails with amazing historical accuracy—if you can get inside
Standing before an unmarked door in a narrow Chicago alleyway lit by red neon, I recited the password in my head. I knocked, hesitantly at first—this was the right place, wasn’t it? Then I waited for something to happen.
Within seconds, the door opened a crack and a woman peered out. I quickly mumbled the two-word password. After a few, long seconds, the door opened, and she ushered us out of the cold into the dark bar.
Room 13 (3222 N. Sheffield Ave.), nestled within the basement of the Old Chicago Inn, bills itself as a true speakeasy. The bartenders here mix and serve only those brands of spirits that were around during Prohibition. This attention to historical detail extends to the mixers too: bartenders measure out each egg white to mimic the size they would have been in the ‘20s, before the advent of superchickens and jumbo eggs.
On this particular evening—just days before the 80th anniversary of the repeal of Prohibition—Nick was tending bar. He waited while our coats were checked before explaining the menu. Each cocktail on it had seen its heydey during Prohibition, though he was willing to go off script; he indulged my husband’s request for a Negroni, and he suggested a pink-hued Polynesian-inspired drink for me.
Drinks in hand, we settled into a cozy corner table near the piano. On Saturdays, live music plays, and we heard rumors that the hostess sometimes sings along.
Over the course of the night, our group of four sipped on nearly every drink on the menu. We tried the Aviation, a purple-tinged gin-based cocktail that gets its colors from creme de violette; The Last Word, on the other hand, appears green thanks to chartreuse. We also introduced our friend to my husband’s go-to cocktail, the Corpse Reviver No. 2, a strong and boozy absinthe-laced drink that Nick informed us was created for day drinking.
With every order, Nick delivered each drink himself, explaining the history behind each. He convinced a tequila-loving companion to try a Picador, a drink inspired by the fact that booze was legal out in open water; partiers would spend hours at sea, mixing whatever was left on the boat into new concoctions. The drink combines tequila, lime juice, and triple sec—a tart precursor to the margarita.
As the cocktails continued to arrive (and just as quickly disappear), I couldn’t help but notice that the joint wasn’t filling up. In fact, the only people who did eventually join us had previous affiliations with the inn. One of them, John, was a former innkeeper, and he had lived in this very basement. He even showed us the plumbing hookup where his laundry machine had stood.
Some revelers may have been turned off by the absence of a “scene” here, but to me, the lack of a crowd lent a sense of ownership to the place, a feeling that we really were part of an underground club. In a way, I almost feel like I’m violating the spirit of the evening by writing about it in the light of day. Even more so, perhaps, because the experience was a singular one: only inn guests and people willing to pay a yearly membership are granted access.
Because of this policy, the speakeasy remains out of the grasp of most casual drinkers. But if you’re willing to go to these lengths—I considered booking a room at the inn just to get inside—I think you’ll fit right in.
But you’ll have to figure out the password for yourself.
Photo credit: Melanie Zanoza Bartelme, Groupon