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A red room with a table flanked by red velvet dining chairs atop a patterned red rug
Photograph: Mallory Korol

The 10 most romantic speakeasies in Chicago

Snag a table for two at these intimate lounges.

Written by Samantha Nelson for Time Out, in association with Ketel One
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Planning a date often centers around where to go for dinner, but the right bar can provide a lower pressure destination or a way to keep a great evening going. Chicago’s tradition of speakeasies—bars hidden underground or within other businesses—dates back to Prohibition but continues to thrive with both recent openings and institutions that rank among the best bars in Chicago. The romance of the Roaring ‘20s is also alive and well, with intimate spots outfitted with couches and dim lights from candles and chandeliers creating the perfect atmosphere to get to know each other while sipping some well crafted cocktails or enjoying the energy of live music. Feel the love at one of these romantic speakeasies.

RECOMMENDED: Check out even more Chicago speakeasies

The most romantic speakeasies in Chicago

  • Bars
  • Wine bars
  • Logan Square

Get a taste of Rome at Testaccio then head down an unmarked staircase to this Parisian-style wine lounge. Sit at one of the red velvet banquettes or throne-like chairs arranged around dark wood and marble candlelit tables and share a bottle of Champagne or something from Soif’s collection of natural wines. On the weekend, DJs provide a soundtrack of house and R&B music perfect for relaxing with a complex cocktail and a plate of cheese and charcuterie.

  • Restaurants
  • American
  • River North
  • price 2 of 4

After a meal of wood-fired bone marrow and handmade pasta at Gilt Bar, walk through a hallway covered with photos to get to The Library. The vintage art, velvet booths and fringed chandeliers will make you feel like you’ve traveled back in time as you sip an old fashioned or espresso martini. Before you leave, step into the photo booth to commemorate a great night out and add your picture to the gallery.

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  • Bars
  • Lounges
  • West Loop
  • price 3 of 4

Tucked beneath the James Beard Award-winning cocktail bar The Aviary, The Office opts for more classic cocktails rather than the spectacle upstairs. Peruse the cabinet filled with vintage spirits and select something to sip or ask the bartender to whip something special up based on your preferred flavor profile. For a really memorable date, book a cocktail class led by one of the bar directors where you’ll learn how to mix two drinks and take home a recipe book.

  • Bars
  • West Loop

Start your date by sharing Peruvian-inspired plates at Stephanie Izard’s rooftop spot Cabra, then head downstairs to Lazy Bird where you can catch live music Thursday through Saturday. Pull up a stool at the bar and watch the bartenders work as they mix up a classic cocktail like a Boulevardier or French 75 and sweeten the experience by digging into double chocolate cake for two. You can also snuggle up on the couch set with small candlelit tables.

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  • Bars
  • Cocktail bars
  • Wicker Park
  • price 3 of 4

Cocktail lovers flock to this James Beard Award-winning bar, which specializes in pre-Prohibition drinks. The space is divided into three candle lit salons, creating an intimate space for sipping a seasonal drink from a menu that’s divided by shaken and stirred options and also boasts a collection of rare spirits. For a super cozy night out, book the fireside experience where you’ll watch a bartender prepare a flight of three drinks from your seat near the hearth.

  • Bars
  • Hotel bars
  • River North
  • price 3 of 4

Start your evening with a great meal of tacos and margaritas at DineAmic Hospitality’s Barrio then head behind the register and through the cold storage room, where you’ll walk through a curtain and into this secret nightclub. While it’s been open since 2017, the space has been largely kept a secret aside from being used for private parties. This year it’s gotten more active, hosting DJs and live music Friday and Saturday nights along with bottle service.

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  • Bars
  • Lounges
  • River North
  • price 2 of 4

See if love is in the cards at the lively speakeasy beneath the Green Door Tavern, which prohibits flash photos and cellphone lights to maintain the mood. Peruse a collection of 100 drinks laid out on custom tarot cards, with a selection changing daily, or nurse a fine spirit while sharing snacks like deviled eggs or pork belly sliders with kimchi. The stage hosts a variety of performances including music, comedy and burlesque so you never quite know what to expect.

  • Bars
  • Cocktail bars
  • East Village
  • price 2 of 4

Channeling the opulence of Paris’ Belle Époque era, Bordel’s candlelit space features velvet couches, tasseled chandeliers and a stage that hosts jazz, burlesque and flamenco performances depending on the night. The drink selection features punch served in glass porrons or hidden in teapots plus classic cocktails like a Sazerac or old fashioned. Have dinner beforehand downstairs at Mama Delia or enjoy late night bites from their menu such as beef tartare with bone marrow aioli or a chorizo sandwich with truffle-aged balsamic.

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  • Restaurants
  • Japanese
  • West Loop

Walk through the back alley behind Komo to find this upstairs lounge modeled after a Colombian castle. Cozy up on one of the pillow-strewn couches and enjoy the Latin vibes with a selection of premium rums or a drink made tableside from a vintage cocktail cart. As the evening goes on the place takes on more of a party atmosphere where you can dance to salsa, merengue and bachata.

  • Bars
  • Dive bars
  • River North
  • price 2 of 4

Pops for Champagne celebrated its 40th anniversary in August by reopening this basement speakeasy, renovating the stone and woodwork that dates back to the 1890s. As a playful spin on the seasonal cocktail menu, the drink list is currently based on Community and will continue to rotate through different TV shows. Every option has its ABV listed so you can select your level of buzz, though if you’re feeling bold you can also opt for a dealer’s choice.

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