Chicago – Bar Crawl

For those looking for a drink, Chicago is a great place to be. The Windy City’s bar scene is outstanding. You can choose from rooftop bars, gorgeous patios, relaxed breweries, and timeless pubs.

But there are even more possibilities to explore. Chicago is filled with speakeasies and underground bars that you have to hunt down to find. Some of these require an exclusive membership, while others are accessible through an inconspicuous door. Hunting down speakeasies to visit feels more like a scavenger hunt than a bar crawl.

During your visit to Chi-Town, embark on an adventure and try to find these eight watering holes. This guide takes you through multiple neighborhoods in Chicago, and we recommend public transportation when following this bar crawl.


Janitor’s Closet

We recommend starting out at Janitor’s Closet, where being nosy is a plus. In the lobby of the FieldHouse Jones hotel, you’ll find an unassuming door leading to a staircase. This staircase brings you to a hallway where you’ll feel as though you shouldn’t be there.

As you venture through the hotel’s basement, look for the door marked “Employees Only.” This is where you’ll find the Janitor’s Closet, a speakeasy that’s definitely true to its name.

Back when the building was Borden Dairy Depot, the room actually did serve as a janitor’s closet. The bar embraces its theme with wet floor signs, mops, tool shelves, and bottles of Pine-Sol.

This speakeasy is one that truly feels hidden and intimate. There’s only one bartender and no more than 15 people can fit inside. Since Janitor’s Closet is relatively hard to find compared to other speakeasies, you and the other patrons feel like you are in on a secret. So when you’re in Chicago, make sure you head down to the basement and drink in the Janitor’s Closet.


The Drifter

ChicagoA six-minute walk from Janitor’s Closet is The Drifter. This location is an authentic speakeasy, having served as one during Prohibition. It’s located in The Green Door Tavern, a casual pub that was once frequented by the gangsters of Chicago.

You can find the speakeasy by walking down the stairs to the bathroom. There you’ll see a door covered in knickknacks, which is the entrance to The Drifter. This dark and secretive cocktail bar is filled with vintage decorations, such as old bottles lined up on top of the bar, vintage road signs, and antiques dispersed throughout the dimly lit area.

The Drifter also takes an interesting approach to their menu. Guests order off custom tarot cards that display the ever-changing cocktails. Past guests have commented that even after multiple visits there weren’t any repeating cocktails.

The Drifter hosts an eclectic mix of live entertainment as well. Performers include belly dancers, jugglers, and burlesque shows. When you sneak into The Drifter, you’ll feel as if you’ve been transported back to the 1920s.


Milk Room

A 10-minute Uber or Lyft ride from The Drifter brings you to Milk Room, one of the most luxurious speakeasies in the city. Milk Room is located on the second floor of the Chicago Athletic Association hotel.


This incredibly exclusive watering hole only has room for eight people, making it one of the hardest speakeasies to get into. Esquire Magazine included them on their list of the “Best Bars in America” in 2017, and Chicago Magazine named Milk Room one of “Chicago’s Best News Bars” in 2016.

The cocktails there contain rare, luxury spirits, such as 100-year-old Bacardi and bourbon from 1948. These outstanding drinks come with a hefty price tag, though. For instance, the Daiquiri #4 features three-year-old Cuban rum, 1950s maraschino liqueur, key lime, and hand-shaved ice, and will put you back $52. Sip on them as you enjoy Milk Room’s fantastic view of Grant Park.


Booze Box

The next stop on your journey is Booze Box, where you can grab a quick meal before venturing down into the secret speakeasy. A Lyft or Uber will get you there from Milk Room in nine minutes, but you can also take the 30-minute walk. Chicago’s Sushi Dokku looks like your everyday sushi restaurant. But in addition to grabbing a roll for lunch, you can hang out in a lively bar with drinks and a fantastic DJ.

To find their speakeasy, walk around the back of Sushi Dokku to the alleyway. This may seem suspicious, but keep an eye out for a red light above a doorway. That’s where you’ll find the entrance to Booze Box, where drinks and Japanese food meet.

Since Booze Box is located beneath Sushi Dokku, the bar has access to its menu. This is perfect for fans of Japanese food who may want to enjoy gyoza, sushi, or a small plate of grilled octopus along with their craft cocktails. Booze Box has everything you need: sushi and spirits. What more could you ask for?


The Office

At this office, you won’t mind staying late. That’s because, at The Office, you can enjoy some delicious cocktails made by knowledgeable bartenders. This tiny speakeasy consists of just one small room, so guests almost always need a reservation. The Office is located underneath an existing bar, The Aviary, which you can walk to from Booze Box in less than 10 minutes.

The cocktails at The Office are age-old favorites crafted with rare, antique liquor. Past patrons have suggested going with the dealer’s choice, so the expert bartenders can create an outstanding concoction for you.



Around the corner from The Office is barbershop Blind Barber, where you may notice many people heading into each night. Are there haircut discounts after dark? Nope! This fully functioning barbershop actually has a speakeasy hidden in the back. It’s called the Backroom, and it’s open until 2 a.m., seven days a week.

This dark, retro bar contains passé furniture, a checkered floor, and outdated, yet charming, wood paneling. The entire bar feels as though it’s been left in the 1970s, which adds to its charm. Various DJs perform throughout the week, keeping the crowd up and dancing all night. So stop by Blind Barber for a haircut, and show it off at the Backroom afterward!


The Violet Hour

ChicagoAfter Backroom, take a 12-minute ride to Damen Avenue. On this street, there’s a large mural with a plain door and a light above it. It looks unassuming, but it’s actually the entrance to the stylish Violet Hour.

You can tell they’re open when the light above the door is on. When you walk in, you’re greeted by a thick, velvet curtain, with the dark bar area behind it.

The Violet Hour keeps its upscale reputation by enforcing a few rules that maintain a classy atmosphere. No baseball hats, no loud conversations, and no cellphone use, for starters.

You’ll feel comfortable while enjoying an expertly crafted cocktail tucked away amongst private booths and intimate seating areas. With this cozy atmosphere, The Violet Hour creates an escape from the outside world.


The Ladies’ Room

Fat Rice, a rustic cafe located less than 10 minutes from The Violet Hour driving, is the perfect place to grab some delicious comfort food. Their menu represents cuisines from around the world, especially Chinese food. This casual eatery is also home to The Ladies’ Room.

Right near the bathroom in Fat Rice is a curtain, which leads to this exclusive speakeasy. The Ladies’ Room requires reservations, as this intimate space is small and in high demand.

They’ve got delicious cocktails with funky names, like Bamboo Pandamonium and Saigon Street Breakfast. One of the most popular drinks is The Thunderdome, which the bartenders set on fire right before they serve it.


At this point you’ve traveled across the city, exploring some of the best speakeasies in Chicago. Keep an eye out throughout your trip, because you never know when you may stumble across another one!