The Drifter Chicago

Reviews

• Adam B. J.

  star star star star star 22 May 2026

  So the speakeasy craze is sweeping the nation.  I've been to them in San Fran, Austin, NOLA, Atlanta, but had to go to one in Chicago where they all started.  
  
  The Drifter was a speakeasy​ back in the day, you can drink while waiting, and they have decent seating so it was a win win.  
  
  Drinks were good, but I've had better.  You're there more for the setting I'd say. I did think it was awesome that the cocktails are on tarot cards.  
  
  We had the Nutella​ sandwich.  That thing was huge and yummy.
  
  Burlesque​ was the ​icing on the cake, though I'm not a fan of a ​contortionist.

• Kate M.

  star star_border star_border star_border star_border 19 May 2026

  When you read online reviews about the best Speakeasy in Chicago, you have your hopes up a bit. Unfortunately, The Drifter was not up to my expectations. We were charged $6 per person for cover because of the "show" and was seated in a "booth" that really meant to be for two people, not three.. In one side there was a guest who was visually uncomfortable to be sharing this tiny space with two other girls instead of one and on the other side there was....well....a trash can. First performer sang for less than 5 minutes and after half an hour of the wait the other two showed up. In total, all the show lasted no more than 20 minutes. Do I think it was worth $18 in cover? No. I think I could spend same amount for three people in Kingston Mines in cover + uber there and we would've had a blast.
  
  Also, the place itself is incredibly small and feels very claustrophobic. There is literally no space between tables and one of the servers had to reach through me to serve drinks for the table next to us, because he could not walk through. Odd experience.
  
  On a brighter side - I liked that specialty drinks were written on tarot cards. Very unusual presentation. Drinks were also well balanced, but, again, pricey. We paid $62 (without tips) for three drinks and barely 20 minutes of performance. Decide for yourself if you think it is worth it, but certainly was not worth to me.

• Alex C.

  star star star star star_border 16 May 2026

  Really cool concept, but left a little disappointed and wanting more!
  
  I'm a sucker for a good speakeasy, and The Drifter had been on my list to check out for awhile. I've been to Green Door Tavern dozens of times and always had a blast, so I was really excited to head downstairs to the Drifter.
  
  We came on a Tuesday night around 9 or so and were seated quickly at a table near the stage. Our server was super nice and attentive. They had some Halloween beverages on special, and I tried one with mezcal. No complaints there. The drinks all night were terrific. Also enjoyed the fortune cookie option! For $10 you get to choose a random fortune cookie and you get what you open. The drinks range from upscale cocktails to Malort  and Jager shots. Try your luck!
  
  While drinks, service, and ambiance were great, I was disappointed there was only one short five minute performance every hour. I had heard from friends who'd previously gone that there were back-to-back performances ranging from magic shows to burlesque. Maybe we chose to go on the wrong night, but I left feeling a bit underwhelmed.

• Max R.

  star star star star_border star_border 14 May 2026

  The Drifter! One of the most love-hate relationships ever.
  
  I've been here a couple times now on Chicago visits. I have returned because I live for the late night entertainment. The bar upstairs is cool and all, but head downstairs for the whimsical evening entertainment. From drag to magic shows, the live entertainment will surely be just random enough to keep your attention.
  
  The obvious cocktail choice is the fortune cookie. It costs $10. Sometimes you get an amazing choice cocktail, whose menu price is $13/$14 and sometimes you break the cookie open and get a shot of Malort. Tragic, I know. It never works out in my favor, but it's always fun to try.
  
  My only qualms with this spot are that they are unwilling to split checks. At the end of a really nice night, my friends and I had to get a calculator out and figure out our bill. There were 6 of us, so it was too many drinks for one of us to grab the bill, but also confusing enough for it to take 20 minutes. I want to give them the benefit of the doubt, but I feel like it would've been faster for them to take care of it.

• Grant A.

  star star star star_border star_border 4 May 2026

  I like the concept of Speakeasies. This one shares some of the theme of the bar above as far as decor goes. Some of the cocktails are presented on tarot cards and there's also a paper menu. There's a cover charge which they're able to add to your ticket/ bill if you're not carrying cash. None of the menu items spoke to me so I ordered a Last Word. There was a performance on the stage that I didn't really vibe with and they were only at the top of the hour. I'm curious what the other ones were like. It was a dude dancing. The staff was friendly. Thought the chairs could have been more comfortable. They say speak easy and I get how people that plan and design bars can interpret that very differently. I guess I was hoping for the lights to showcase that with some dimmer lighting or colored lighting to put you more in a speak easy mood.