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A circular bar lit with candles at Rose Lounge
Photograph: Courtesy of Adalina

5 new speakeasies in Chicago worth a visit

Prohibition ended nearly 100 years ago, but the speakeasy tradition is alive and well in Chicago.

Written by Samantha Nelson for Time Out, in association with Ketel One
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During Prohibition, Chicago was home to numerous hidden bars where people could enjoy illicit drinks. While it’s been more than 100 years since alcohol was first made illegal, speakeasies continue to quietly pop up around the city.

“There's such a romance to them,” said Kim Klinger, beverage manager for Jaleo and its basement speakeasy Pigtail, which opened in October. “Something feels really special about a bar that’s a little bit hidden, a little bit dark, and a little bit sexy.”

Adalina owner Matt Deichl said speakeasies like the Rose Lounge, which launched on the Gold Coast restaurant’s ground floor in March, are beloved because they provide a more intimate experience than a typical bar. “I think they are really geared towards having some drinks with friends, catching up and having a great conversation.”

Restaurants add speakeasies to provide diners with an easy way to extend their night out by grabbing a drink before or after their meal in a space that feels very different, even if it’s under the same roof.

“Jaleo is really bright and rowdy,” Klinger said. “Then you go downstairs and you have a different vibe, something that's a little bit more intimate. It's a really fun way to integrate those two floors and give people a unique experience.”

They also allow for more menu experimentation. Adalina’s cocktails have to be fairly simple because the restaurant is so busy, but Rose Lounge allows you to sit back and watch bartenders work on elaborate drinks like The Centerfold, which blends mezcal, aperol, yellow chartreuse and pineapple with just a hint of habanero. Pigtail offers its own tasting menu with four cocktails and three wines paired with Spanish bites with an emphasis on jamon iberico.

“It's a great way to see what the chefs are working on and playing with and come out of there pretty satisfied,” Klinger.

If you want to feel like you’re in the know, check out one of these five new speakeasies. Heads up: You don’t need a secret password, but you might need a reservation.

5 exciting new speakeasies in Chicago

  • Restaurants
  • Latin American
  • West Loop
  • price 2 of 4

Purchase a ticket and enter through the Carnivale’s back alley to visit this monthly pop-up featuring rotating entertainment such as live music or mentalist shows. Like the Latin restaurant downstairs, the speakeasy pops with bright colors, though celebrity photos on the walls give it a bit more of an old school vibe. Stop in after dinner to enjoy a craft cocktail and the show at one of the small tables positioned right near the performers.

  • Restaurants
  • Cajun
  • River North

Named for Lulu White, one the most successful French Quarter madams, the basement space below New Orleans-inspired restaurant Storyville creates a boudoir vibe with couches, gilded mirrors and tasseled lamps. Settle in and order a classic cocktail like a negroni or sidecar or a signature sipper such as Be My Druidess, mezcal blended with papaya, lime and activated charcoal. Burlesque dancers, magic shows and live music add to the sexy fun.

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  • Bars
  • Cocktail bars
  • River North

As the name implies, the basement bar beneath chef Jose Andres’ Jaleo focuses on both pork and cocktails in a playful atmosphere with neon lighting and pigs hidden around the space. Snack on hand-carved jamon iberico paired with a showy cocktail like the Nitro-Frozen Pomada, made with gin, Spanish lemon soda and bergamot, before heading upstairs for your meal. You can also have a full dinner at Pigtail by ordering a five-course tasting experience.

  • Restaurants
  • Italian
  • Rush & Division

Take the golden elevator at Adalina down to Rose Lounge, where you can grab a seat at the horseshoe-shaped central bar or the plush velvet couches around the perimeter. Lit by candles and chandeliers and decorated by floral art to go with the name, the bar offers an extensive selection of champagne and spirits plus complex cocktails. You’ll also find premium spins on classics like the Walnuts Old Fashioned made with walnut liqueur, hazelnut and chocolate-walnut bitters. Reservations are required for most of the night to ensure it doesn’t get too crowded to have intimate conversations. 

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  • Bars
  • Cocktail bars
  • Armour Square
  • price 2 of 4

A Lunar New Year pop-up at Chinatown staple Moon Palace led to the launch of the neighborhood’s first cocktail bar. The restaurant became take-out only post COVID, though you can enter a door that looks like it leads to the kitchen to step into Nine Bar. The neon lit industrial space serves highballs and complex cocktails like the Mahjong Money (mezcal, Japanese whiskey, matcha, honey, lemongrass and ginger). You can get the party going with a sake bomb or relax and snack on cold sesame noodles or crab rangoon.

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