Speakeasies In Chicago, Illinois, USA

1. Room 13 at the Old Chicago Inn

Room 13 is a Prohibition-inspired speakeasy (brazenly declared on its website) located in the Old Chicago Inn. This secretive establishment is only open to inn guests and Room 13 members, who are required to follow a cocktail and business casual model. Going along with its theme, patrons can sample a range of cocktails representative of the Prohibition. Luke, Room 13’s bartender, is also extremely knowledgeable about the history and nuances from that era.

Room 13

Address: 3222 N Sheffield Ave, Chicago, IL 60657, USA

Tel. No.: +1 (773) 472-2278

Website: Room 13

2. The Office

Situated right below The Aviary, The Office takes the secrecy of speakeasies to the next level with just 14 seats available, so your best chance of snagging a place is to make a pricey reservation through its official website. For successful “applicants” however, it is well worth the time, effort, and money. Aside from the inevitable sense of exclusivity exuded around its dimly lit lounge decked with antiques and art, patrons will have a chance to try liquor from past ages, as well as a wide range of drinks made from premium ingredients.

The Office

Address: 955 W Fulton Market, Chicago, IL 60607, USA

Website: The Office

3. The Drifter

“When you step into The Drifter, you’re stepping on the same floor where drifters have tread for over 100 years.” True to its official description, The Drifter is an authentic 1920s speakeasy located in the basement of the Green Door Tavern. There are no reservations, and its 37 tables are given on a first come, first served basis. The Drifter features over 100 cocktails uniquely presented on Tarot cards, which probably gives you an idea of the unusual music and entertainment this speakeasy offers, including horror film nights.

The Drifter

Address: 676-8 N Orleans St, Chicago, IL 60654, USA

Tel. No.: +1 (312) 631-3887

Website: The Drifter

4. The Violet Hour

The Violet Hour, which takes its name from TS Eliot’s The Wasteland, is a James Beard Award-winning speakeasy located in the heart of Wicker Park. It features exquisite furnishings and an extraordinary cocktail list to match. The Violet Hour is also shrouded in secrecy like many other speakeasies; guests have to abide by a strict set of rules, such as not being allowed on their cell phones, and not being allowed to bring anyone to the establishment that “you wouldn’t bring to your mother’s house for Sunday dinner.”

The Violet Hour

Address: 1520 N Damen Ave, Chicago, IL 60622, USA

Tel. No.: +1 (773) 252-1500

Website: The Violet Hour

5. Watershed

Pop by the Watershed Bar and you will find a set of stairs to the corner, marked with nothing more than a “W”. This will lead you to the Watershed’s basement speakeasy, whose call to fame is its range of craft beers, artisanal spirits, and fine wines from the Great Lakes region. It also features an extensive cocktail list. Watershed is also popular for its relaxed atmosphere, a respite for many from the hustle and bustle of Chicago. Pay the Watershed a visit on Sundays if you are a fan of vintage music.

Watershed

Address: 601 N State St, Chicago, IL 60654, USA

Website: Watershed

6. Untitled Supper Club

An American Whiskey-inspired cocktail list and delicious food whipped up by six-time Michelin Bib Gourmand recipient Frank Mnuk — Untitled Supper Club has all the elements of an amazing speakeasy. It is a typical subterranean, unmarked Prohibition-era establishment located at the end of a rather inconspicuous set of stairs next to a CVS store. A large Al Capone poster greets you as you make your way into a posh setting with dim lighting and shelves of about 500 types of American whiskey. Live music and entertainment are held five nights a week, each with varying themes, from vintage jazz to rock.

Untitled Supper Club

Address: 111 W Kinzie St, Chicago, IL 60654, USA

Tel. No.: +1 (312) 880-1511

Website: Untitled Supper Club

7. The Library

Located below the popular Gilt Bar is its more intimate space, The Library. Decked in posh red velvet seats and — true to its name — an extensive collection of curated literature from Chicago, New York, London, and Paris. Patrons down by The Library will also have Gilt Bar’s food and drink menu, consisting of sumptuous main dishes like coal-fired rib eye, and a generous selection of cocktails, wines, and beers.

The Library

Address: 230 W Kinzie St, Chicago, IL 60654, USA

Tel. No.: +1 (312) 464-9544

Website: The Library

8. The Bassment

The Bassment is a classic Chicago speakeasy located below The Hampton Social. Enter through a secret door, and step into another world behind thick, black curtains — a world inspired by the 1960s’ British Invasion movement, with gold accents prevalent throughout its interior, brick walls, a full-length stage, as well as a proportionate mix of velvet and leather couches. The Bassment also features its very own range of signature cocktails with pretty interesting names, such as “The Bathtub”, “Tea Time”, and “Million Dollar Negroni”. Live music is held every night, featuring in-house bands that add to a unique experience like no other.

The Bassment

Address: 353 West Hubbard Street Lower Level, Chicago, IL 60654, USA

Tel. No.: +1 (312) 386-5778

Website: The Bassment

9. Bordel

One of Chicago’s most sought after speakeasies, Bordel, is the brainchild of Daniel Alonso, whose portfolio also includes other popular establishments like Black Bull and Fulton Market Kitchen. Its Bohemian design is inspired by Paris’ Belle Époque and Chicago’s Prohibition era, and its premises are often packed full with a wide variety of entertainment, from jazz musicians to burlesque performers, magicians, and more. Bordel also features its own unique classic drinks like “Widow’s Kiss”, an apple brandy cocktail, and “Zosh”, a vodka mix.

Bordel

Address: 1721 W Division St, Chicago, IL 60622, USA

Tel. No.: +1 (773) 227-8600

Website: Bordel

10. Baby ATLAS

Down in the basement of the Matilda Bar is Baby ATLAS, a speakeasy whose name probably does not match its nature, but do not be fooled; it is actually a buzzing place awash with loud music and uninhibited dancing. Matilda and Baby ATLAS are a tag-team act — the former serves delicious food, and the latter, a reasonable range of cocktails. Baby ATLAS’ focus is quite clearly, the celebration of music and a sense of anonymity. Do note that you have to be at least 23 years old to be allowed in.

Matilda-Baby ATLAS

Address: 3101 N Sheffield Ave #1, Chicago, IL 60657, USA

Tel. No.: +1 (773) 883-4400

Website: Baby ATLAS

A slice of Capone in your cocktails

Chicago’s speakeasies are full of character, proudly embracing the Prohibition era that has shrouded them in the sort of secrecy that has endeared them to patrons from all walks of life. Check them out, and be a part of Chicago’s underbelly.