My Top 10 Favorite Speakeasies in Chicago

My Top 10 Favorite Speakeasies in Chicago

I think one of the top questions I get in my inbox from readers (besides how I started becoming a blogger) is what are the best speakeasies in Chicago to visit when they are in town.  Chicago is, after all, known for being one of the best cities in the world for speakeasies thanks to our man Al Capone and the Prohibition Era.

Well...I decided to compile a list for all of you since I keep copy-and-pasting the same ones over and over in my emails.  Here is a list of my Top 10 Favorite Speakeasies in Chicago.  Bottoms Up!

1.     Violet Hour

Wicker Park, 1520 N Damen Ave.

Violet Hour: my absolute favorite spot in the city for a drink.  Chances are you have walked by this famous Wicker Park institution and not even known it.  The main door is always camouflaged behind a massive, ever-changing mural that is painted across the building’s wall. 

Step inside this place and feel like you are being transported to an Alice in Wonderland-esque world.  The cocktails are to die for, and they have a no cell phone rule—so put them away!

2.     The Drifter

River North, 676 N Orleans St.

Located in the basement of The Green Door Tavern you will find this vintage-looking REAL speakeasy from back in the day.  Just walk downstairs like you are going to the bathroom and knock on the bookcase (that is actually the door) that is on your right.

The drinks are presented on tarot cards for you to order from, and they have live music and burlesque shows through the week.  *Check out the old door hanging on the wall inside because that is the original door from the Prohibition days!!

3.     Door No. 3

Wicker Park, 1572 N Milwaukee Ave.

So I kind of have a soft (and angry) spot for this place because I got my fake I.D. taken away at the Double Door when I was underage... BUT—all is not lost because Door No. 3 is Double Door’s speakeasy basement lounge and it is really fun.

You’ll find the entrance in the alley off of Damen and under the Blue Line tracks.  You’ll find DJs spinning and drinks flowing down here.

4.     Untitled

River North, 111 W Kinzie St.

Untitled is like the mega-venue of speakeasies in Chicago.  You will probably miss the entrance unless it is a busy night of the week when there is a line outside the door.  Despite the line, it is definitely a place to check out.

There are 3 massive rooms when you walk downstairs, and each of them has a totally different vibe.  Sit in the dining hall (with private booths) for some dinner.  Enter the library for a cocktail, to catch an old black and white movie, or to gaze at the giant wall of private lockers that holds the members' booze. Last, you can head to the back room for live music and entertainment.

5.     Double A

River North, 108 W Kinzie St.

Just across the street from Untitled is another great spot in the basement of Mercadito.  Down there you will find the cute, tiny speakeasy Double A.  Drinks are delicious and space is limited, but it is always a great time.

6.     The Green Mill

Uptown, 4802 N Broadway St.

Another Prohibition-original, this place used to be a popular hangout for the (in)famous mobster Al Capone and other celebs of the day.  Capone’s favorite booth is still in the lounge located directly west of the short end of the bar.

Nowadays, you can catch amazing jazz music and other live performances while sipping your cocktails.

7.     Barrelhouse Flat

Lincoln Park, 2624 N Lincoln Ave.

When you walk into this place, you wouldn’t think there was any type of speakeasy vibe to it at all.  All you have to do is just head to the back of the bar, go up the stairs and there you go!

The upstairs bar here is a great spot to have a more quiet experience than you will have downstairs, and you’ll be served much better cocktails.  The decor is to die for!

8.     Bordel

West Town/Wicker Park, 1721 W Division St.

Going back to my Latin roots, Bordel gives me everything I need in a speakeasy.  Open the door to the right of Black Bull (which is one of the best tapas restaurants in town), take the stairs up, and the unmarked door will be on the left.

You can expect amazing cocktails and live performances from music to burlesque.  My personal favorite:  Flamenco Dancing on Saturday! Ahhh... it’s wonderful.

9.     Three Dots and a Dash

River North, 435 N Clark St.

Chicago gets pretty damn cold most of the year, so us locals need a tropical escape from time to time.  Thankfully, there is Three Dots and a Dash to tickle that fancy.

This tiki inspired speakeasy is located in the alley behind Bub City.  Once inside, follow the massive wall of skulls down the stairs to enter the tropical drinking hole. You’ll find a massive drink list that resembles something you would get at a hotel resort on the beach. You and your friends could even order a giant treasure chest filled with dry ice and Dom Perignon to share at your table!

10. The Office

West Loop, 955 W Fulton Market

This spot is definitely the trickiest of all speakeasies on this list to get into.  It is located in the basement of The Aviary (which is an unbelievably amazing cocktail lounge that you must go to as well) and you basically need an invitation to get inside.

You can try to politely ask around upstairs for an invitation, or book a private party for up to 16 people and you are almost guaranteed to get in.  The cocktails here and upstairs at The Aviary are among the best in all of Chicago.


What are your favorite speakeasies? Comment below with more great locations!

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