Chicago’s Best Modern Speakeasy Bars

Chicago’s Best Modern Speakeasy Bars

From live Burlesque performance lounges to intimate, hidden basements, Chicago is full of jazzy places to enjoy a drink. Here are my choices of Chicago’s best modern speakeasy bars for drinking great cocktails and soaking up the atmosphere in the Windy City.

Chicago was once notorious for its abundance of speakeasies and the flagrant bootleggers and rum-runners who ran the show. While many of the Prohibition-era secret watering holes have since shut their doors, there are quite a few underground drinking spots where the true spirit of the speakeasy lives on.

If you’re keen on drinking in some of the Windy City’s most unique drinking quarters, then look no further. Here’s my round-up of Chicago’s best modern speakeasy bars.

 

Traveling to Chicago and keen on drinking in some of the Windy City’s most unique drinking quarters? Take a peek at my round-up of Chicago's best modern speakeasy bars. www.willfulandwildhearted.com

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Chicago’s best modern speakeasy bars

 

The Drifter in River North

Chicago's Best Modern Speakeasy Bars www.willfulandwildhearted.com

  • Recommended for: Speakeasy bar underneath Green Door Tavern pouring craft cocktails and offering live entertainment.
  • Address: 676 North Orleans Street, Chicago, IL 60654, USA
  • Opens: Wednesday to Saturday, 5 p.m. – 2 a.m.

The Drifter is particularly interesting as it’s actually a restored 1920s speakeasy. It sits below the city’s historic Green Door Tavern and is unlike any other bar in town. Patrons can sit back and enjoy whatever unique entertainment is on for the night along with the daily rotating cocktail menu. The Drifter has a capacity of 37 people, so it’d be best not to arrive with a large group. The intimacy factor certainly makes it one of Chicago’s best modern speakeasy bars.

How to enter The Drifter: Walk through the Green Door Tavern straight to the back and chill out in the waiting room until there’s space to enter. Bottom’s up!

 

The Violet Hour in Wicker Park

Chicago's Best Modern Speakeasy Bars www.willfulandwildhearted.com

 

  • Recommended for: Creative cocktails and small bites make up this sophisticated, stylish speakeasy bar.
  • Address: 1520 North Damen Avenue, Chicago, IL 60622, USA
  • Opens: Sunday to Friday, 6 p.m. – 2 a.m., Saturdays 6 p.m. – 3 a.m.

The secret hideaway of The Violet Hour is a haven for cocktail enthusiasts and hipsters alike. Not only is there no labeled entrance, but there is no cell phone use allowed inside the lounge, nor are customers able to order bomb-style shots. It’s a truly modern twist on the speakeasy revolution, offering pricey cocktails in exchange for the privacy from rambunctious crowds. The Violet Hour is essentially the epitome of Chicago’s best modern speakeasy bars.

How to enter The Violet Hour: Look for the giant wooden door on the building across from neighborhood favorite taco joint Big Star. Hop in line if there is one (there will be), otherwise, knock a few times on the door to be let in. Let the magic of the night take over.

 

Punch House in Pilsen

Chicago's Best Modern Speakeasy Bars www.willfulandwildhearted.com

 

  • Recommended for: Hidden basement speakeasy bar with a vintage air serving up creative and classic punch style cocktails.
  • Address:1227 West 18th Street, Chicago, IL 60608, USA
  • Opens: Sunday – Friday: 6 p.m. –  2 a.m., Saturdays 6 p.m. – 3 a.m.

Located just below the classic American tavern Dusek’s, the Punch House is ideal for those who are out in a group and on the hunt for one of Chicago’s best modern speakeasy bars. This basement bar will aptly take you back in time. The wood panelled walls and 1970s inspired décor make for a Midwestern sanctuary. This place is known for serving some of the best – you guessed it – punch in town, so order a bowl and dance the night away.

How to enter Punch House: Walk into the considerably more polished Dusek’s and take the stairs into the basement. Have a blast in the past.

 

The Library in River North

Chicago's Best Modern Speakeasy Bars www.willfulandwildhearted.com

 

  • Recommended for: Speakeasy lounge bar with vintage library decor serving cocktails and the same upscale American menu as Gilt Bar upstairs.
  • Address: 230 West Kinzie Street, Chicago, IL 60654, USA
  • Opens: Thursdays 5:45 p.m. – 11:30 p.m., Fridays and Saturdays, 5:45 p.m. – 12:30 a.m.

The Library is the perfect romantic hideaway to end the night after a few cocktails at Chicago hotspot Gilt Bar. While it may not be easy to find, once you’re in, you’ll be thankful. The red-velvet furnishings and dark, wooden tables create the perfect atmosphere for an intimate conversation or catch-up. Not only is this one of Chicago’s best modern speakeasy bars, it’s certainly a cozy spot regardless of it’s secret appeal.

How to enter The Library: Once you’re in Gilt Bar, head downstairs through the velvet curtains near the bar. If you still can’t find it, ask one of the hosts and they’ll be more than willing to assist you.

 

Bordel in Bucktown

Chicago's Best Modern Speakeasy Bars www.willfulandwildhearted.com

 

  • Recommended for: Craft cocktails and drinks fuel the vibe at this bordello-inspired, speakeasy lounge bar offering a variety of live performances.
  • Address: 1721 West Division Street, Chicago, IL 60622, USA
  • Opens: Every day from 9 p.m.- 2 a.m.

Bordel is Chicago’s ultimate modern-day speakeasy. While it’s garnered recent attention, it’s still located in a completely unmarked location. Music lovers can rejoice: there’s weekly live music scheduled. Wednesdays lineup features jazz, head over on Thursdays for some bossa nova and Fridays and Saturdays: dance the night away to some flamenco tunes – perfect for this Spanish-style secret space.

How to enter Bordel: The bar is located on the second floor of famed tapas joint Black Bull. The door is unmarked, but once you walk up the red stairwell, you’ll know you’ve arrived.

 

Have you been to any of Chicago’s best modern speakeasy bars? Let me know in the comments below!

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11 Comments

  1. September 26, 2017 / 7:10 pm

    I think that the Library would be my first choice. There was a time when I was looking for places where to work from in my small town in Romania, and of course, there weren’t many places where I could stay for hours. But places like this ones seem to be a good match that meets everybody’s needs.

  2. September 27, 2017 / 11:36 am

    Oh my gosh, I want to go to all of these places! I love classic cocktails, and these look like top-notch places to check this out! I think the Violet Hour is my top pick for my next trip to Chicago! Thanks for sharing!

    • September 27, 2017 / 10:55 pm

      The Violet Hour is so lovely inside and a great spot. I love the fact no phones are allowed inside!

  3. Katie
    September 27, 2017 / 1:16 pm

    I feel like I’m all set for some good nights out if I visit Chicago! I actually wouldn’t have thought to go out and visit any bars but this totally makes me want to – especially getting some punch at the Punch House!

    • September 27, 2017 / 10:54 pm

      Awesome! Let me know if you have any other questions! Chicago’s known for its food and drink options, and so it’s all part of the touristy experience as well 🙂

  4. September 28, 2017 / 3:05 am

    I so wish there was a Speakeasy list like this for my location. I love Speakeasy’s and this is a great list for when I visit Chicago. I’d probably go to the Bordel in Bucktown first. It’s great that they have weekly live music.

    • September 28, 2017 / 3:59 am

      Agreed! I hope you get to visit soon! Best city!

  5. September 28, 2017 / 3:18 am

    I’M PLANNING ON SURPRISING TIM NEXT YEAR WITH A CHICAGO WEEKEND BDAY GIFT SO THIS IS PEEEEERFECT!!! I’ve recently become obsessed with speakeasies! Love love love the decor of the The Library (anything book related I’m pretty much into) but I am totally onboard with The Violet Hour’s no cellphone policy! Bookmarking for later use 🙂

    • September 28, 2017 / 3:58 am

      Girl, I’ll give ya alllllll the Chicago tips! How exciting! You will love it.

  6. September 28, 2017 / 5:58 am

    Like the way The Drifter works. Seems like my kind a place when I head to the states next summer. The windy city does have some good speakeasies. Reminds me the prohibition era when booze was illegal and these underground speakeasies were the way to go!

  7. September 30, 2017 / 2:55 pm

    Wow, I truly love your choices of Chicago’s best modern speakeasy bars for drinking great cocktails and soaking up the atmosphere in the Windy City. The list of places that you have posted here is really interesting and I fin them such a great place to chill for a Friday night while waiting for the next day to arrive. I also love all the photos that you have captured. It actually speaks how great and interesting these places are.

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