Stay Classy This Winter With a Spiced Pear Tom Collins
1. Room 133222 N Sheffield Ave, Chicago
2. JIMMY at The James Chicago610 N Rush St, Chicago
3. East Room2828 W Medill Ave, Chicago
4. Double A108 W Kinzie St, Chicago
5. Everleigh Social Club937 W Randolph St, Chicago
6. Three Dots and a Dash435 N Clark St, Chicago
7. The Violet Hour1520 N Damen Ave, Chicago
8. Door No. 31572 N. Milwaukee Ave, Chicago
9. The Office At Aviary955 W Fulton Market, Chicago
This secret speakeasy is home to old slot machines, prohibition era-style cocktails, and lots of dark, musty detail to make you really feel like you've stepped back in time.
Located on the Near North Side, this cocktail bar and lounge is a sophisticated and inviting space that offers an upscale, unpretentious environment to enjoy an innovative cocktail.
Follow a single red lightbulb to an unmarked door off Milwaukee Ave. in Logan Square, and you’ll eventually find your way into the music venue and speakeasy that is East Room. Though its entry may lead you to believe it’s on par with the rest of the pretentious, unmarked cocktail bars of the world, one step inside and those expectations shatter. East Room is a beer-and-a-shot joint with live music, 30 beers, and 40 whiskeys to choose from. And it’s cash only, but show your receipt from the on-site ATM to the bartender… it’s your ticket to a shot of whiskey, on them.
DA is an intimate, speakeasy-style lounge centered around an "open bar" work station for the mixologist, giving him no room/barrier to separate him from his thirsty customers, who surround the station in dark, low-slung leather booths with filament bulbs hanging overhead from the wooden ceiling, which female woodchucks have long been trying to break through.
One of the city’s most legit speakeasies (and definitely the sexiest), this brothel-style private club offers memberships which allow you unfettered access to events like Naked Girls Reading (where naked girls, um, read), Bordello Drawing Club (where you can paint nude models), and the invite-only Thieves event where fine bottles of bourbon are voraciously consumed.
Three Dots and a Dash is a tiki-themed speakeasy in the back of Bub City that's pouring out crazy tropical cocktails in vessels like glass skulls and treasure chests.
The first clue that this Wicker Park cocktail lounge is different from its neighboring bars is the house rules, the first of which forbids cellphones. The second is the James Beard Award-winning cocktail program. The drink menu is organized by alcohol type, and though you'll find vodka, brandy, tequila, gin, and rum cocktails, The Violet Hour's speciality seems to be whiskey, and a sip of the eponymous Old Fashioned confirms it. This is your Chicago destination for a night of refined, expensive drinking -- there is a dress code, and it's fancy.
The team behind Wicker Park's Double Door brings you Door No. 3, a speakeasy lounge with a secret door on Damen, just under the El tracks. It has a stellar drinks menu created by none other than owner Sean Mulroney.
This classy speakeasy is located below The Aviary, and is only accessible by invitation, or booking a private party (up to 16 people). Prepare yourself for $20+ cocktails and creative small plates with a similarly decadent price tag.