Chicago, IL

The Top Six Secret Speakeasies in Chicago

Natalie Frank, Ph.D.

These are some of the best hidden speakeasies in Chicago and the secret to getting into each one.

Prohibition took place from 1920 until 1933 in America, and Chicago was a city very much affected by that era of restriction. Most people who have lived near or visited Chicago have heard of the famed gangster Al Capone and his involvement in the Prohibition era. Not as many are aware that many of the original Prohibition Era Speakeasies from that time still exist today in Chicago. The best ones still have an aura of secrecy around them and take some know-how to gain admittance, but the effort is well worth it. Here are some of Chicago’s top speakeasies with tips on how to get in to enjoy all they have to offer.

The Violet Hour 1520 N. Damen Chicago, Illino
The Violet

One of the first bars in Chicago to serve craft cocktails The Violet Hourserves seasonally themed, pre-prohibition style cocktails. This award winning bar is known for its artisanal menu of popular and creative drinks. There are three interior salons and large marble var which are lit by the candlelight from the clusters of tables. Should you have trouble deciding on a drink, the bartenders will be happy to whip you up something special so long as you follow the house rules: "No Grey Goose, no bombs of any kind, no Cosmopolitans."

If you get hungry there are seasonal small plates such as red curry squash crostini with pickled Spanish octopus, marinated finocchiona with pickled vegetables, and sardines with house-made crackers and Tabasco. To get in, you have to locate the door handle which is hidden somewhere within the large mural painted on the bar’s exterior.

The Chicago Magic Lounge 5050 N. Clark St. Chicago, Illinois

Check out this video of the various experiences at The Chicago Magic Lounge:

When you approach the Chicago Magic Lounge, you’ll probably think you are in the wrong place. Instead of the entrance to a magic club, you’ll find the door to a rather dingy laundromat, with nothing but washers and dryers everywhere you look. But if you look around you’ll notice a door sized washer. Open it, walk through and you’ll be transported to a bar which is like no other.

Vintage posters adorn the walls. Trinkets and magic memorabilia, books and other magic items can be viewed as you enter and around the club and provide ambiance.

Roving “Chicago-style” magicians travel from table to table performing tricks up close. This style first became popular in 1915 when magic bars began opening in Chicago. Clubs were transformed into speakeasies when prohibition began.

There is a theater that seats 120 with cabaret style seating, and a 43 seat theater that is more intimate. After buying your ticket for the show, you’ll be directed to get in line in the library. Looking around you may be confused as there doesn’t seem to be a door anywhere nearby.

Don’t worry, the host will grab a book from a shelf and the fireplace will slide open to reveal another hidden door. Beyond it is a lounge, which is a relatively small space with Art Deco architecture. It’s a speakeasy within a speakeasy.

Cocktails names are magic themed including How Houdini Died (Parce 8 Year, Rhum JM 80, Aperol, Lime Juice, Pineapple Juice, OJ, Iced Tea, Angostura Bitters), Abracadabra (El Tesero Platinum, Lime Juice, Luxardo Maraschino, Simple Syrup, Creme de Violette), and Smoke and Mirrors (El Buho Mezcal, Amaro Montenegro, Letherbee Fernet) which is magically set alight.

If you are hungry there are a variety of food options including shareables like roasted olives and goat cheese with marinara, different kinds of sliders, and small bites such as Prosciutto Wrapped Dates stuffed with gorgonzola. Top you light meal off with one of their sweets such as s’mores, caramels, truffles or peanut butter bon bons.

The Drifter 676-8 N Orleans St., Chicago, Illinois
The DifterPinterest

This speakeasy is truly a hidden gem in Chicago that many people don’t know exists. It’s tucked away on the lower level of the Green Door Tavern, Chicago’s oldest bar. The Drifter holds tight to its roots as the speakeasy it was back in the times of prohibition and Al Capone. During prohibition, people would enter a building a few blocks away and get into the bar through a window, which has since been covered over.

Staff may mention the secret club to you and how to get in. If not, you can ask and they’ll tell you how to get on the list (if there is one) and where to find the door. If you want to find it on your own, head downstairs and find the door hidden behind the bookcase by the restrooms. If there is a wait someone will be there taking names. If there isn’t, knock on the wooden door and you’ll be let in.

This bar is simple, unpretentious and intimate. It seats only 40. Drink lists are printed on tarot cards and there’s a rotating selection of drinks. You can visit there half a dozen times and never have a repeat cocktail on the menu. You can also ask the bartender for something totally unique to satisfy your taste buds.There is a small stage with occasional performers such as belly dancers, jugglers and burlesque dancers.

The Office 955 W Fulton Market, Chicago, Illinois

Located below The Aviary is one of the most exclusive speakeasies in town, backed by famed chef Grant Achatz. Gaining entrance to this den of high-priced cocktail art is not easy and not cheap. If you eating at the Aviary, you may be approached by a manager and quietly invited downstairs. If that doesn’t happen, you can inquire of your server if there is room for any additional guests at The Office. If you are not eating at the Aviary, you must make an advance reservation, which includes a $50 deposit to hold your spot which will be applied to your bill.

Before going, if you are unaware of how to palm a tip for a maitre d’, transferring it from you to them while shaking hands, it’s a good idea to practice before going. This is how they will give you one of the coveted keys that unlocks the nondescript door to the small bar. Be sure to plan ahead as reservations are not easy to get as there are only five seats at the counter and three small tables in this mini-bar. The Office is furnished with heavy leather seats and a gorgeous metal bar top..

This speakeasy is known for classical cocktails with a twist that often involves rare, and antique spirits, including a cognac that dates back to the 1940’s and sells for $265 an ounce. Some of their antique liquors are older than prohibition itself.

If you can’t decide what to order, tell the bartender what your favorite flavors are, then ask for a “dealer’s choice” and let them surprise you..

As you would expect from an establishment associated with Chef Grant Achatz, there are decadent dishes that are different even from what is offered in the Aviary, which are exclusive to The Office.

The Janitors Closet 312 W. Chestnut St., Chicago, Illinois
The Janitors ClosetPeter Ranvestel/

This is one of the most unique speakeasies you’ll ever visit. As the name implies, the bar is located in a former janitor’s closet. To get in, you first need to make a reservation. Go down to the lower level of Chicago’s FieldHouse Jones Hotel and look for the “Employees Only,” sign. Ignore it and go right in and you’ll find yourself inside an old janitor’s closet. The speakeasy is decorated with retro relics salvaged from old schools, flea markets, and thrift stores. The dimly lit Janitor’s Closet has 15 seats along with school bus-inspired booths and petite round tables lining the back wall.

Cocktails feature global booze & local ingredients. Some of their more popular drinks include The Brown Line (Mezcal, Tequila, Pineapple Gum Syrup, Tamarind, and Lime), the Last Swerve (Mezcal, Green Chartreuse, Hibiscus-infused Maraschino Liqueur and Lime), and Field’s Martini (Gin, Dry Okra Vermouth and Bitters with a Lemon Twist). If you are in need for a pick-me-up try their Cafe Con Leche Flip (Blackstrap Rum, Coffee, Heavy Cream, Simple Syrup and Egg Yolk).

The Booze Box 823 W Randolph Street, Chicago Illinois
The Booze BoxEater Chicago

This is the most unusual speakeasy on the list as it is an Eastern establishment which is located in the basement of Sushi Dokku. To get in, head down the alley which is located just south of Sushi Dokku. Find the door with the Booze Box sticker near its handle and head on in. The Booze Box is a dark, sexy bar, illuminated by red lanterns. Here you’ll find Eastern-inspired drinks like Japanese highballs served alongside Japanese “trail mix” snacks accompanied by a laid-back vibe. Their sake flights are not to miss.


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