Everyone likes to be in on a secret. It’s an exhilarating feeling – you’re special, knowing something your coworkers, family or friends don’t. We’re going to share 7 Must-Try Chicago Speakeasies in this blog post.
It’s even more exciting knowing a city’s secrets, and trust us when we say Chicago has plenty. Our Free Chicago Walking Tours are loaded with them.
When most people think of a night out in Chicago they think of well-known areas like River North and Gold Coast–perfectly fine choices no doubt, but what they don’t know is that Chicago has some of the best-hidden bars in the country. You can find Chicago speakeasies in the strangest locations throughout the city. It’s also a great way to explore new neighborhoods in Chicago.
Violet Hour
1520 N. Damen, Chicago, IL (Wicker Park)
Source: The Violet Hour
Perhaps one of the most well-known Chicago speakeasies, The Violet Hour may also be one of the classiest. Located in the bumping and trendy Wicker Park neighborhood, The Violet Hour will make you feel like one of Chicago’s elite. The Violet Hour has no door, sign or light. If you’re not careful you will walk right past the door which is typically painted over and a part of a larger mural that covers the entire front of the building. After ten minutes a bouncer will take you into a waiting room– a sign that you’re in. You must adhere to the strict dress code, never order anything that you’d drink at a frat party and refrain from using your phone.
What you need to know: No reservations. No use of cell phones inside. No baseball hats. No reservations, first come first serve. No ‘O’ bombs or jaeger bombs or any kind of bombs. No Budweiser.
What you need to try: Frites and aioli for a snack and wash it down with their version of a Manhattan – appropriately called a Brooklyn.
Booze Box
823 W Randolph St, Chicago, IL (West Loop)
Source:Sushi Dokku
Many people have heard of the restaurant Sushi Dokku in West Loop. It’s located in the arguably the hottest restaurant “district” in Chicago today. Sushi Dokku has neighbors with names such as Au Cheval, the Girl and the Goat and The Publican. Randolph Street is a gem amongst the restaurant and bar world of Chicago. But we digress. We’re talking about Booze Box here, the bar in the basement of Sushi Dokku that many that have dined there don’t know about. You have to walk 10 yards south to an alley behind Sushi Dokku where you will see a lonely bright red sign– the entrance to Booze Box. The atmosphere and what they are serving is just as unique as their entrance. Japanese street food, cold draft sake and a rotation of DJs spinning next to the guests at the bar all make a visit here worthwhile.
What you need to know: Booze Box is open only on the weekends – Thursday, Friday & Saturday – starting at 6pm.
What you need to try: Chill Gin Mojito
East Room
2354 N Milwaukee Ave, Chicago, IL (Logan Square)
Source: Yelp
To be fair– East Room isn’t a speakeasy all the time. They open their doors to the main street when there is a special event or concert, but all other days you can only get in through the back door. The first time we went there it took us 20 minutes to find the place. Your phone will be telling you you’re standing right in front of it but you won’t see a soul near you. Everyone will be across the street at all the other bars lined up pretty in a row. But don’t give up! Just walk to the back alley until you see a strong looking man leaned up to the wall. He is your way to the second floor– a mix of cheap drinks, good music and wooden benches for good conversation.
What you need to know: Cash only! So, you know…bring cash or someone that has cash.
What you need to try: BYO-Vinyl. Yes, Bring Your Own Vinyl, as in records – East Chicago crowd-sources their music on Mondays.
3 Dots and a Dash
435 N Clark St, Chicago, IL (River North)
Source: Facebook
Consider this a new-age speakeasy. A new-age tiki-lounge-inspired speakeasy. This place is far from your traditional prohibition-era underground hush place. It’s still more well known than the other bars, but 3 Dots and a Dash is one of the most fun speakeasies in town. It boasts a Polynesian type theme complete with mini umbrellas in the drinks and almost any type of rum you could possibly dream of. You’ll often see large 21st birthday parties, bachelorette parties and groups of bar crawlers. This is a great speakeasy to have a drink at before hitting the clubs in the area.
What you need to know: It’s tricky to find. Walk up Clark St, then head east on Hubbard and go north up the alley. On your left (west) will be a small hanging sign that says “3 Dots and a Dash” – congratulations, you have arrived.
What you need to try: For those in a large group or with plenty of disposable income – or both, you definitely should order the “Treasure Chest” – a $400 cocktail that is served in an actual treasure chest on bamboo shoots carried in by a couple of waiters. Smoke (dry ice) billows out, the drink is lit up and the waiter pops a bottle of Dom Perignon and pours it into the concoction. Everyone at the table gets a giant straw and has at it.
Door No. 3
1572 N Milwaukee Ave, Chicago, IL (Wicker Park)
Source: Facebook
Another speakeasy located in Wicker Park, Door No. 3 puts you in the mood with a secret entrance in the alley behind the Damen Blue Line stop. What makes Door No. 3 special is the live music. The DJs are skilled spinners that know how to keep people dancing and keep the party going. The interior isn’t shabby either with sexy leather furniture and blue lighting perfect for a chill, relaxed date night. It is also a go-to destination to kick off a night of bar hopping in Wicker Park.
What you need to know: There is no food served here. They have a small vending machine in the corner to satisfy your hunger. They aren’t known for any fancy cocktails either. Hipster beers like PBR and Tecate are available as well as your traditional mixed drinks.
Room 13
3222 N Sheffield Ave, Chicago, IL (Lakeview/Wrigleyville)
Source: Old Chicago Inn
No questions about this one – Room 13 is definitely a speakeasy. Or maybe it should be a “speak hard” because it’s not easy to get into. Get it? Ha.
Located a half a mile south of Wrigley field like many speakeasies Room 13 is a part of another business: The Old Chicago Inn Bed & Breakfast. This place has all the markings of a speakeasy. Garden unit, check. Classic American cocktails, check. Dress code, check. Oh, and you seriously need to work to get in.
There are 3 options and only 3 options to get into this place:
- Stay at the Inn and you will receive an invite
- Buy a membership (aka become a member)
- Be a guest of a member
Mic drop. That’s it. If you are not fitting into one of those buckets you will not get in.
What you need to know: This place is seriously awesome.
What you need to try: Their cocktail flight. Reserved exclusively for guests of the Inn simply add the “Speakeasy Flight” to your reservation and you will receive a flight of 4 cocktails while the bartender explains the history of each drink. Cost is $55 for two people.
The Office
955 W Fulton Market, Chicago, IL (West Loop)
Source: Yelp
Ah yes, The Office. This will be sort of a good news-bad news situation. Let’s start with the bad news. This is another really tough one to get into. The good news? It’s underneath one of our favorite bars in the city which you can get into (if you have a reservation): The Aviary.
The Office is a 14-seat VIP speakeasy located beneath The Aviary. The bar features drinks and food that you will not find on The Aviary’s menu. If you’re a commoner just having drinks and food upstairs you might notice people going in and out of The Office and wonder – how do I get in? Well…you need to be invited. The staff at The Aviary invite guests to The Office. That’s it. Good luck!
What you need to know: If you have made it inside The Office and have to use the bathroom you’ll take a key from the bar, use the “commoners” restroom and get back inside The Office using the key. And it’s not exactly cheap either. $20+ cocktails, $30+ appetizers, Make sure you bring your wallet!
What you need to try: The level of attention you receive from the staff and bartenders is incredible here. Instead of ordering off the menu tell the bartender your favorite spirit and let them come up with something that will impress. And if you’re in the mood for dessert order their ice cream sundae. OMG.
If you have the time give all of these spots a try while visiting. And let us know in the comment section how the night went. We look forward to hearing from you!
