The 5 can’t miss hidden Chicago Speakeasies

Step into the captivating world of Chicago speakeasies, where the city’s rich history intersects with its vibrant nightlife scene. In the heart of Chicago, speakeasies thrived during the Prohibition era, offering an escape from the restrictions of the time. 

Concealed behind discreet entrances and hidden within the city’s unassuming buildings, speakeasies in Chicago became havens of secret revelry. While we didn’t get a chance to visit them all (damn livers!), we were able to indulge in some amazing craft cocktails at the ones we did visit. 

Short on Time? Here are the key takeaways: 

• Most Chicago Speakeasies don’t open until 5 PM (even on the weekends)
• Almost all of the speakeasies on this list have food
• In our opinion, don’t miss The Booze Box or The Drifter

Map of the 5 Speakeasies in Chicago

The 5 Can’t Miss Chicago Speakeasies

1. The Drifter

• Hours: 
  • Wednesday – Friday: 5PM – 2AM
  • Saturday: 5PM – 3AM
  • Sunday – Tuesday: Closed
• Food Available: Snacks only
• Reservations Available: No, first-come, first-serve

Nestled beneath the unassuming exterior of The Green Door Tavern, The Drifter offers a speakeasy experience like no other. This hidden bar invites patrons on a nostalgic journey back to the Prohibition era.

The Green Door Tavern was built in the late 1800s but has been open and operating since 1921 making it one of the oldest bars in Chicago. Many of the tavern’s original fixtures are still in place to this day and it offers decorative memorabilia from the past century throughout the bar. 

Descend the stairs as if you’re heading to the restroom, and find yourself transported back to the bygone era behind a hidden door that resembles a bookshelf. Inside, the 45-seat bar oozes with 1920s charm, complete with live entertainment and more vintage decor. 

Their extensive cocktails list of over 100 options changes daily with each night’s offerings depending on which tarot cards are selected for that day. We hesitate to name the cocktails we had because they very well may not be available when you visit, but regardless, they are going to be expertly crafted cocktails that are delicious – all while relishing in the intimate setting and vibrant energy of the crowd.

The Drifter promises a unique experience and live entertainment every night. As mentioned above, the rotating selection of tarot cards dictates the evening’s libations which ensures an element of surprise and excitement for visitors. And as for that live entertainment, when we visited, we were delightfully surprised with a more-risque-than-expected burlesque “show” (it was only a couple of minutes long).

With its commitment to preserving history and providing patrons with an unforgettable evening of revelry, The Drifter captures the essence of Chicago’s rich and storied past and is a must-visit speakeasy in Chicago (in our humble opinion). 

Note: since there are live performances every hour, there is a $7 charge per person added to your bill. However, we thought it was worth it for the performance we saw. 

2. The Booze Box

• Hours: 
  • Tuesday & Wednesday: 5PM – 10PM
  • Thursday: 5PM – 11PM
  • Friday & Saturday: 5PM – 12AM
  • Sunday & Monday: Closed
• Food Available: Full menu, Japanese food
• Reservations Available: Yes, for parties of 2-8

We found the Booze Box by accident on our first trip to Chicago back in 2019. We were next door for a drink and saw this neon sign in the alley. After 5 years, the memory of this Chicago speakeasy stayed with us and we were anxious to try to it again. 

In the back alley of the sushiDokku restaurant, look for a bright red neon sign. Enter through the door (don’t be alarmed that the door is between a bunch of dumpsters), down the staircase and you’ll find yourself in a secret Japanese oasis offering an incredible selection of Sake and Japanese Whiskey.

The Booze Box doesn’t have a website. If you try to google the location, the restaurant will pop up. You just gotta trust us, this place is worth the visit. 

While the upstairs sushiDOKKU offers a fine-dining experience, venturing downstairs to Booze Box sets the stage for an unforgettable evening. Dim, warm lighting and low ceilings create an intimate atmosphere and while we didn’t eat here, the food looked scrumptious and we found ourselves growing hungrier with every passing dish. We arrived around 7 on a Friday and it was packed. There are limited seating options so we highly recommend making a reservation if you want to eat here as well. 

In our opinion, the cocktails we ordered here blew away every other cocktail that we tried on this list. Sam got the Muraski crafted with Dry White Rum, Ube Syrup, Egg White and Lime, while Chris opted for the Eastern Medicine made with Glenfiddich 12 year scotch, Islay Scotch, Ginger Wasabi and Lemon. 

Between the drinks, the back alley entrance and the incredible selection of Japanese libations, we think Booze Box might be one of the most underrated speakeasies in Chicago. 

3. Blind Barber

• Hours: 
  • Tuesday – Saturday: 5PM – Close
  • Sunday & Monday: Closed
• Food Available: Yes, small bar bites
• Reservations Available: Yes, through their website

Step into the whimsical world of Blind Barber, a hidden bar in Chicago’s bustling West Loop neighborhood. The Blind Barber is a novel fusion of barbershop and speakeasy. 

By day, it operates as a traditional barbershop, but by night, it transforms into a vibrant speakeasy with a cozy, dark ambiance and plush leather seating. 

At first glance, Blind Barber appears to be just another barber shop, complete with the iconic spinning multi-color spiral tube outside. We’ll admit, we were completely fooled when we walked by it as people were legit getting their hair cut when we peered through the window! 

Once inside the barber shop, ask for the speakeasy. You’ll be escorted through an unmarked door inside the barber shop which opens to this sophisticated bar. 

We visited during happy hour and enjoyed two of their HH cocktails: Southside Richie and Paradise Ginza. Both were simple, yet delicious and hit the spot for both of us. 

Despite its unassuming facade, Blind Barber harbors a not-so-secret speakeasy that’s become a hotspot for party-goers in the city. Whether you’re popping in for a haircut during the day or craving some late-night snacks and cocktails, this Chicago speakeasy has you covered.

4. Three Dots and a Dash

• Hours: 
  • Sunday – Wednesday: 4PM – 12AM
  • Thursday & Friday: 4PM – 1AM
  • Saturday: 2 PM – 1 AM
• Food Available: Yes, mostly shareables
• Reservations Available: Yes, via OpenTable

Tucked away in Chicago’s River North neighborhood, Three Dots and a Dash is a speakeasy-style paradise, offering a unique blend of island charm and tiki cocktails. 

To enter this oasis, walk down the alley directly next to Firecakes on West Hubbard. You’ll see the tiki art painted on the building; then look for a door among the artwork.  As you descend into the tropical hideaway, you’ll find yourself surrounded by unique Polynesian artifacts, a bamboo and straw roofed bar and colorful Caribbean decor. 

Their menu boasts an impressive selection of over two dozen classic and original tropical drinks, meticulously crafted using the freshest ingredients served in statuesque ceramic mugs. 

Sam ordered the Royal Hawaiian which was served in a massive bowl complete with a smoking tiki statue, flower, umbrella and a large chunk of pineapple. This delicious concoction was made of Gin, Almond Orgeat, Lemon and Pineapple. Chris ordered their signature drink, Three Dots and a Dash, made of Aged Martinique Rhum Agricole, Aged Guyana Rum, Lime, Orange, Falernum, Allspice. 

While we didn’t eat on this visit, the table next to us ordered the Pu Pu Platter that is served with a tiny grill so you can skewer your food over an open small flame right at your table. 

If you are looking to escape the bustling streets into an immerse tropical atmosphere, Three Dots and a Dash should be on the top of your Chicago speakeasies list! 

5. Fox Bar

• Hours: 
  • Wednesday: 6PM – 1AM
  • Thursday – Saturday: 6PM – 2AM
  • Sunday – Tuesday: Closed
• Food Available: No
• Reservations Available: No, first-come, first-serve

Curl up into Fox Bar, an intimate, cozy hideaway concealed within the mezzanine level of Soho House Chicago. 

Once inside the Soho House, look for a large fox painting hanging along the staircase on your right. Walk up the stairs and look for the saloon doors with the words “Bar Service Only”. Swing through the doors to enter. 

Despite its smaller size, Fox Bar offers a seasonal craft cocktail menu that perfectly compliments each season. We happened to be visiting in the winter and their menu offered a variety of drinks to warm you back up (think Hot Toddy). 

Chris ordered the La Estrella Del Norte, a Mezcal-based drink with lemon cacao, mole bitters and orange oil while Sam was feeling something a bit more classic and went with a vodka gimlet. 

The bar has very limited seating so get there early or be prepared to wait. We were very lucky to snag 2 seats at their bar, but this place was packed when we left. 

Boozy Tours in Chicago

If the idea of trying to find these speakeasies in Chicago is intimating OR you are looking for more boozy fun, check out these tours on Viator:

• Private Speakeasy Pub Crawl in Chicago with Local Historian: If history and speakeasies are your passion, this tour was made for you. Complete with a driver, this is a solid option for a large group looking to bar hop. Note: It’s a bit pricey.
• Haunted Chicago Booze and Boos Ghost Walking Tour: If you want to put the boo in boozy, this much more affordable option combines history, haunts and libations. While the speakeasies aren’t on this guide, you’ll get to learn the secrets of Chicago’s past.

In wrapping up our exploration of Chicago speakeasies, it’s evident that these stealthy establishments offer more than just cocktails—they provide a captivating journey into the city’s storied past. From hidden alleyway entrances to glamorous underground lounges, each speakeasy reveals a unique facet of Chicago’s Prohibition-era heritage. 

Whether you’re a local seeking a new haunt or a traveler craving an authentic nightlife experience, delving into the world of speakeasies in Chicago promises an unforgettable adventure through the city’s hidden gems.