Secret Speakeasies in Chicago: How to Enter
Speakeasies can be defined as prohibition-style 1920s-themed bars that are exclusive to only those who know about them. They may not be easy to see or get into. With Chicago’s rich history, there are plenty of speakeasies hidden in the city. Some pricier than others, yet worth the visit. Chicago has more speakeasies than you know. Check out Stay In Chicago’s list of secret speakeasies and how to enter.
The Office
955 W Fulton Market
(312) 266-0868
The Office - Extremely hard to get into with only 14 seats available is known as The Office, located in the Fulton Market District. You must book a pricey reservation on their website. You may have an easier time getting in by being personally invited by someone you know at The Aviary, the exclusive bar upstairs. The entrance involves an unmarked metal door inside The Aviary. This dimly lit lounge is filled with pristine art. An interesting aspect of The Office is that there’s no menu here. All drinks are $20, with the exception of $375 for an ounce of liquor from past eras.
The drifter
676 N Orleans St
(312) 631-3887
The Drifter - Built right after the Great Chicago Fire was one of the most popular speakeasies in Chicago during prohibition. This speakeasy is actually easy to get into, being located at The Green Door Tavern. Although there’s no sign, just knock on the wooden door after you go down the stairs. The drinks are fantastically unique and inspired by tarot cards, being written on and selected at random each night. You may or may not see a burlesque show here.
Milk room
12 S. Michigan Ave
(312) 792-3515
Milk Room - Costing $50 a ticket to get in is absolutely worth it here at Milk Room Chicago. Located at the Chicago Athletic Association Hotel is this eight-seat speakeasy that focuses on using vintage spirits that are extremely hard to find in other bars. You must arrive on time for your time slot visit. The $50 ticket fee does go towards your bill. And yes, Milk Room is way better than Cindy’s Rooftop.
Violet hour
1520 N Damen Ave
(773) 252-1500
Violet Hour -The entrance may be given away by the amount of people waiting to get inside on the weekend. There’s a secret tour located on the facade of the building. This popular Wicker Park speakeasy doesn’t allow standing. There’s also a number of other strict rules such as no talking on a phone, no hats. This bar loves to display their rules all over the dimly lit bar. The drinks are truly works of art. You will appreciate the mixology here.
Watershed
601 N. State St.
(312)266-4932
Watershed - Located inside Pops for Champagne is this low-key downstairs speakeasy. This one has a huge cocktail list, yet also serves beer, wine, and artisanal spirits. It is located in the heart of River North. This is a more intimate speakeasy, being perfect for a date or a weeknight drink. To get downstairs, go to the door that says W.
the library
(312) 464-9544
The Library - This hidden gem is located underneath the wonderful Gilt Bar in River North. Gilt Bar already has the feel of a speakeasy, so you can only imagine what it’s like down under. The service here is stellar. It is the perfect place to experience romance, being quiet and dim. Simply go down the staircase at Gilt Bar and enjoy a scotch surrounded by a library of unique books.
Bordel
1721 W. Division St
(773) 227-8600
Bordel - This unmarked speakeasy is true prohibition-themed bar, featuring burlesque and flamenco dancing. The menu consists of Spanish and Mediterranean influences. This Wicker Park speakeasy will have you coming back for more. To get in, you’ll have to open the door to the very right of the Black Bull. Go up the steps and open the door on your left. What’s better than drinking alcohol out of a tea set?
Untitled supper club
111 W. Kinzie St
(312) 880-1511
One of the biggest speakeasies in Chicago is the gigantic Untitled Supper Club, boasting 18,000 square feet. This River North lounge makes up many different cocktail rooms. Live music is one of the best parts about this speakeasy, along with the delicious food menu. Go downstairs and check out their huge selection of Whiskey. If you like burlesque shows, come here on Thursdays.
