“It’s so hard to find!!!!” When it comes to speakeasy’s those words are music to my ears. Ya’ll know I love a good speakeasy! Prohibition is over, but some Chicago establishments have brought back the concept. Looking for the unmarked entrance, heading up or down the elusive staircase, and finally arriving amongst the cool kids in a sexy dungeon like atmosphere. Good music, great drinks, and the ambience are sure to set the mood for the night. I’ve compiled a list of my favorite tried and true Chicago speakeasy’s both old and new. Hope you enjoy the list and keep me posted at firstname.lastname@example.org if you have a spot I should check out.
111 W Kinzie Street, Chicago, IL
I don’t claim to know all the intricate details and origin behind each Chicago Speakeasy. My first introduction to the speakeasy scene was at Untitled. There was much buzz around this spot when it opened and I knew to look for the unmarked door. Once inside you walk down the huge staircase into 10,000 square feet of adventure. There’s three different rooms to choose from and each offers a different experience. I’ve been to a derby party in the Whiskey Library, danced the night away to a Prince impersonator in the main dining room, and had a birthday celebration followed by a menu tasting dinner in the parlor. Each experience was different, but great memories were created all in one space. Definitely pop by speakeasy cherry at Untitled and have been in search of cool speakeasy’s ever since. Tip: It’s no longer on the menu, but ask for the Pistol Smoke Whiskey Based Cocktail…my favorite drink there. It’s STRONG!!
1939 W North Avenue, Chicago, IL
Dorian’s is fairly new and opened up late 2018. I love Speakeasy’s that masquerade as something else. In order to get to Dorian’s you enter through a record shop with vinyl selections. There’s even a sound booth you and your party wait in to be seated. Once inside…the vibe blows you away. We went on a night when they had a live jazz band. Expect creative cocktails and globally inspired shared plates. If you’re there with a group I would suggest ordering one of their shared drinks. We went with the Stormy Daniels that came served in a fun disco ball. Food wise we shared the Bay Scallops, but I’m eyeing the Mushroom Wonton’s for next time. Side Note: The vinyl records are available for sale.
676 N Orleans Street, Chicago, IL
It took me a minute to find this one the first time I went. You enter through Greendoor Tavern, follow the signs to go downstairs to the bathroom, then knock on the unmarked door on the right. It’s funny cause I felt like 90% of the patrons upstairs didn’t know this spot exists. Once seated you get tarot cards, not to tell your fortune, but to order your drinks. 🙂 Such a cute concept! There are also burlesque shows and a small food menu. Not the type of place to come to hungry. Food options are very limited. TIP: Before you sit down ask if there will be any entertainment charges for the performance that evening.
416 N Desplaines, Chicago, IL
I had the pleasure of going to Chit Chat before it opened to the public and I’m glad I did because I can definitely see this place being the new hot spot. Esthetics are so important to me and right away you can tell lots of care was put into the exterior and interior of the space. The suspense starts as you enter through the walk way with the huge CHIT CHAT and LIPS printed on the outside wall. Once you make it through the gate and down the beautifully golden draped staircase my word (or words) once you enter are “Grown and Sexy.” Everything from the beautifully placed ceiling light bulbs, to the color scheme is a turn on. The DJ had us jamming and when the DJ isn’t in the booth the curated playlist from owner Dustin Drankiewicz is soooo smooth and may I say a little old school, which I LOVE. We had several shared punch bowls that night, but my favorite was the Jager Colada cocktail. Side note: There’s a little area upstairs reserved for the VIPs to “chit chat.” Such a cute spot!
948 W Fulton Market, Chicago, IL
Need a haircut…then a drink? This is another one of those cool kid spots where the front is totally different from what’s going on in the back. It’s funny when you enter in and see customers getting their hair cut and then walk past to enter the speakeasy Blind Barber. Space is small and it’s ALWAYS packed. I’ve been for a birthday party and had a good time. Tip: If you want to sit down and not stand all night go during the week day. It’s ALWAYS ALWAYS packed on the weekend!
660 W Lake Street, Chicago
So I don’t know if Money Gun is “technically” a speakeasy, but I added it to the list because it definitely has that speakeasy vibe. You enter through the restaurant Saint Lou’s Assembly (took me a while to figure that out. LOL) I’ve been here on several dates and girls night outs and it’s been a crowd pleaser. Music is always on point, I always order the tasty meatballs as a snack, and OMG the drinks are 100. I like to sit at the bar to watch the presentation as they light the drinks on fire. Just in case you don’t see this happening make sure to let the bartender know you want to see your drink set on fire. Trust me they’ll know what you mean. TIP: If you haven’t gotten my tip by now….it’s to ask to see your drink set on fire. DUH. LOL.
5121 S. Harper, Chicago, IL
So please don’t fact check me, but I think the absolute newest Speakeasy on the scene is The Hyde. The Hyde like its namesake is located in Hyde Park. Once again I had the pleasure of checking out this speakeasy before it opened to the public. (Past article click here) The Hyde plays off the mobster mentality with a huge photo of AL Capone when you enter. Try to sneak your picture in real quick because this speakeasy has a NO cellphone policy. The owner Jovanis Bourgoub wants us to enjoy the company were with and the live entertainment. Expect a rotating food menu and a heavy focus on Cognac based cocktails. Oh did I mention you need a password to enter? Tip: To get the password needed to enter DM their Instagram page @theHydechi to make a reservation.
1721 N Division Street, Chicago, IL
You know I couldn’t do a speakeasy round up list without including my tired and true Bordel. My first experience here was on a 4 hour date (we loved it so much) and I’ve been coming back ever since. Head up the stairs of the bar Black Bull and you enter into a red dungeon. You’ll want to follow Bordel on social media because their always having burlesque performances and even Jazz sometimes too. This past year I went to see a really good performance by Sam Trump. The red velvet couches are inviting and so are the craft cocktails. Tip: Great place for large groups to get cozy in the huge sexy booths.
905 W Randolph Street, Chicago
You know what’s Darling? The Darling. 🙂 Yet another speakeasy that masquerades as something else. You enter through a small flower shop in the front. Once inside you have the option of going to the enchanted ballroom upstairs or heading to the intimate library downstairs. Both serve cocktails and food. I had a mini photoshoot with my friend here NYE in the fireplace area. The décor is very antique and grand. The cocktails are made extravagant and beautifully presented. Tip: If you’re really hungry larger plates are served upstairs in the ballroom.
The Press Room
1134 W. Washington Blvd, Chicago, IL
The Press Room is another one that’s not necessarily a Speakeasy, but it has the characteristics of one. The wine bar is located in the basement of the Publishing House Bed & Breakfast. The Pressroom feels cozy and inviting. I had previewed the space before it opened over a year ago and tried different wines and cheeses. Their charcuterie board is pretty amazing! The atmosphere was intimate and the space is used for events as well. Tip: This would be an awesome place for an engagement party and to rent out the rooms upstairs at the bed and breakfast. Such a unique space.
613 N Wells Street, Chicago, IL
Why just listen to music when you can sing your heart out? At Blind Dragon you can Karaoke the night away in their private Karaoke rooms. There’s a minimum to reserve a room, but the deposit goes towards your food and drinks. I’ve been a couple of times now and the music is definitely a draw. Both times it’s pretty much been hip hop/rap. The last time I went Phor from the reality tv show Black Ink Crew Chicago was there and performed. That was unexpected and made for a really fun night. Each time I’ve went I definitely have noticed people dancing versus standing around, which is rare at most lounge/speakeasy’s. The cocktails here are also fun with some creative names. Tip: Don’t think it’s too early to reserve a Karaoke room a few weeks ahead of time. They get reserved fast. Generally rooms are booked out on the weekends.
3222 N Sheffield Ave, Chicago, IL
So I saved the most authentic speakeasy for last. Room 13 is located inside the Old Chicago Inn. It’s a private prohibition-era style speakeasy. You enter through the irongate and YES you definitely need the password which changes weekly. What makes Room 13 unique is it’s membership based. You can visit two times before applying for a membership which currently is $100 for 13 months. Drinks are reasonably priced and the bar offers more old school drinks than frilly drinks we’ve come accustomed to. I want to say it’s definitely one of those spots you should go check out for yourself. From the chaise lounge, to the slot machine, to the phone booth, to the antique cash register….this place screams old school speakeasy. They offer live entertainment and reservations are a must! Tip: To make your reservation contact the manager Luke at Luke@oldchicagoinn.Com.
Sooooo how’d I do??? I know some of you might be screaming, but you left off The Violet Hour, Sparrow, The Watershed, Heavy Feather, Todos Santos, or The Office. NO…I didn’t leave them off purposefully. I just listed the speakeasies I’ve been to in the last two years. Although I haven’t been to The Office yet and plan on trying it out really soon. Hope this list helps and stay tune…..next up will be doing a round up of Chicago’s best Happy Hour spots. Cheers to the New Year!!
Other list you should check out:
Tavi J. – Best Date Night Spots
Tavi J. – Chicago Best Rooftops
More from my site