Two years ago, Abraham Conlon and Adrienne Lo styled a surplus room between Fat Rice and Fat Rice Bakery into an intimate 18-seat cocktail lounge awash in crimson light. Behind a heavy red velvet curtain, Chinese pinup girl posters plaster walls—aesthetic decisions in line with Chinese gambling halls and red light districts from Macau during the mid-19th and 20th centuries. A cabinet of booze stocks Japanese whisky, Cognac, and Champagnes, in addition to myriad house-infused spirits. Beverage director Annie Beebe-Tron weaves a menu of East meets West intoxicants, such as A Dangerous Summer, which mixes rhum agricole with Indian cashew distillate feni, rose, grapefruit, and lime. Note: Reservations are required. 

Pass through longstanding, kitsch-filled The Green Door Tavern, and descend stairs to reach The Drifter, a cozy cocktail enclave that debuted three years ago in an original Prohibition speakeasy space. Decorated with vintage artifacts that surround a long bar and performance stage, here one can sip a lengthy list of craft cocktails while watching juggling acts or burlesque performances. 

New York and Los Angeles export the Blind Barber hit Chicago last year, introducing the city to an unlikely, and seemingly dangerous, duo of haircuts and booze. Push past the white-washed salon room to find a retro cocktail lounge serving a bevy of blended beverages, plus a short list of spirit-friendly snacks.

One floor above Slippery Slope, The Heavy Feather is Scofflaw Group’s ode to old school fern bars of the 1970s. Think peacock-print wallpaper, gold embellishments, and plush booths, plus a roster of classic cocktails with contemporary twists. 

Enter the laundromat, press the spin-cycle button, and a door gives way to Chicago Magic Lounge, a new early 20th century-themed performance venue and bar. Divided between various small rooms and one central space with a stage and two levels of seating, guests can suck down exotically-flavored tipples, in addition to a few beers and wines. 

Watershed—the retro-designed basement bar below Pops for Champagne—pays homage to the Great Lakes region and its many craft liquid producers, from beers to wine to the harder stuff. The vibe here is casual and comfortable, with a particular focus on seasonal and limited edition local craft brews. 

While The Booze Box is located right below Sushi Dokku, to enter one must locate the nearby alley, then spy a neon red arrow which indicates the bar’s door. Once inside, expect a collection of Japanese snacks and Japanese cocktails laced with Asian ingredients like matcha, yuzu, and wasabi.

Room 13 is the 1920s-themed speakeasy located within Old Chicago Inn, and entrance is reserved for hotel guests and private members. Both reservations and proper attire are required to imbibe Prohibition-era cocktails made with top-shelf booze.