Coming to prominence during the controversial prohibition era, speakeasies flourished throughout Chicago as meeting places and watering holes for citizens looking to circumvent the law. While prohibition is now long gone, these bars to a troubled time still exist, and most have retained the secret entrances that defined the scene in the early 19th Century.
Many spots double as wine bars, jazz clubs, or even karaoke venues and serve some of the finest cocktails and local brews in Chicago. In order to dive back into a time where a night out meant getting creative, check out these 10 speakeasies that require a little work and research to enter.
10 Violet Hour
In order to begin your evening within Violet Hour, visitors will need to locate the concealed door handle set within the mural on Damen Avenue. Once it has been found, give it a push and, if you are lucky, a night of historical hijinks sipping on the smoothest cocktails in the city will follow.
The list of rules includes no cell phone use within the prohibition-themed lounge, no baseball hats, and no guests that wouldn’t be approved of by mother for a Sunday dinner. Violet Hour demands decorum within its thick curtained walls and will accept nothing less.
9 The Drifter
A genuine speakeasy from the days of prohibition, The Drifter rests beneath the Green Door Tavern and needs to be accessed through the hidden staircase at its rear.
Restored in recent years to bring it into modern times, The Drifter has a genuine vintage feel that has history crawling all over you from the moment of entry. The capacity is small, just 37, but the wait will not be in vain thanks to unusual entertainment and a lengthy list of delicious drinks just waiting to be devoured.
8 The Ladies Room
This intimate space holds just 20 patrons, so you may need to make a reservation in advance, which thankfully is not as tricky as actually getting inside. Look for the small red light within Fat Rice Bakery and, once granted admission, the actual entrance is behind the counter.
Featuring vintage Asian pin-up art, flaming bowls of alcohol including the famous Burning Bird, and some of the coolest music in town, The Ladies Room was the perfect night out in the time of Al Capone, and it has only gotten better in the intervening years.
7 East Room
Not so much a secret entrance as completely absent of advertisement, East Room is entered through a back alley door with no markings save for a small red light revealing its position. The inside is equally dimly lit, but there is also a bright outdoor space covered by graffiti art that gets plenty of use in the summer months.
Drop in for live bands and DJs most evenings and nightly drink specials that will have you feeling like a 1920s mobster in no time. There are also plenty of themed nights to get the imagination and feet moving in this Chicago institution.
6 Hush Money
Named for a notorious incident from Chicago’s past when Cubs pitcher Mordecai Brown had a run-in with the mob that ended in bribery, this stylish speakeasy features creative cocktails and local beer that will leave you in no doubt as to its classic Chicago heritage.
As an added bonus, and something that would have been especially sought after during the prohibition, Hush Money sports one of the country’s largest selections of collectible, vintage liqueurs. Always check the price tag before placing an order when you are several drinks deep.
5 Chicago Magic Lounge
Those needing to do some laundry will have the best chance of locating the entrance to this unique speakeasy thanks to the cleverly placed opening inside the adjacent laundromat.
Once inside, marvel at the unexpectedly large theatre space where local and international magicians ply their trade and wow guests with their modern takes on the mysterious art form. Slowly sip a house cocktail such as ‘How Houdini Died’ or ‘Sleight of Hand’ and snack on pork belly sliders while a night of trickery plays out around you.
4 Blind Barber
Resting cheekily behind a fully-functioning barber shop, this dark and grungy late-night spot may be hard to find, but it is not difficult to enjoy a raucous evening within its wood-paneled walls.
Prepare yourself for a night on the dance floor with a cocktail and grilled cheese sandwich while reclining in vintage lounge furniture that gives Blind Barber a sensational retro feel. The beauty of this Chicago hotspot is that you don’t need to get your hair done in preparation—you can have it sorted while you wait in line.
3 Room 13
One of the more exclusive speakeasies in town, Room 13 is accessible only to members and guests of the Old Chicago Inn. If you happen to be lucky enough to know or meet someone with the key, get dressed in your finest attire before sliding in and pulling up a stool at the bar to enjoy classic cocktail favorites from the time of prohibition.
If you do happen to get lucky and discover where the secret alleyway entrance is, you won’t be able to go any further unless you possess the ever-changing password as well. Hotel guests will receive an invite to the bar, so that may just be your best way to ensure a night in the always-lucky Room 13.
2 Janitor’s Closet
Hidden inside boutique hotel FieldHouse Jones, Janitor’s Closet requires visitors to take the leap of faith of walking through a door labeled ‘Employees Only.’ The reward for curiosity and courage is an intimate setting laced with unique cocktails and seating that gives the impression of an iconic yellow school bus.
Containing just 15 seats, the name of the bar was not pulled randomly from the sky. The space is, in fact, a genuine old janitor’s closet. Everything has been kitted out with finds from local flea markets and thrift shops, giving this speakeasy a vintage feel that will not soon be forgotten. Assuming you don’t hit the cocktail bar too hard, of course.
1 The Library At Gilt Bar
This library-themed speakeasy will serve you classic cocktails with a local twist and even feed you delicious meals from neighboring businesses if you are really lucky.
Finding your way into the remarkably beautiful bar begins when making your reservation. You will actually need to contact the Gilt Bar, an upstairs friend of the Library, and request seating downstairs. If you are granted entry to the book-laden repository of wonder, then look forward to an evening of scotch-sipping and seafood-scoffing, the likes of which you cannot experience anywhere else.