Chicago Speakeasy Guide – Secrets of the Prohibition Icon

Bucket List Item 2024:  See Stevie Nicks in concert.
Oooh, what’s that?
Stevie Nicks is opening for Billy Joel in Chicago in June?
Well, I guess we are going to Chicago.
What else should we do there?
How about we visit a few Speakeasies?
What?  Speakeasy?  Well, I suppose it is for research purposes.

You should know our Speakeasy Guides are our favorite niche content. And when you think of Speakeasies, you no doubt envision roaring 20’s, mobster-run, prohibition-era Chicago. So this was destined to be an iconic trip.

Starting off with The Best Kind of Speakeasy on the Planet

Bold statement, I know, and why is that?  Because Sushi Suite is a sushi speakeasy, and easily one of the best culinary experiences we have had. In the Lincoln Hotel in Lincoln Park, Sushi Suite has 60-minute seatings, for 6 people at a time.  So, it has a very exclusive, intimate feel to it.  It is 17 different sushi plates, with the “optional” sake flight add on.

Sister Side Note (ssn) – I’m not sure we understand the meaning of “optional” when it comes to food, drinks, or anything remotely upgrade-y, luxurious.

You enter through an unmarked red-framed hotel room door for Suite 202 on the second floor. You are shown to the bar to wait.  The bar has cool, inventive cocktails with a Japanese flair to them (and some smoke if you order right).  Once the earlier seating clears, you and your 4 new besties are escorted to the sushi bar and introduced to your chef. He then prepares a line up of amazing, fresh Nigiri with slight twists for each selection of fish.  They were amazing! We kept declaring each one our new favorite.

It was our sushi chef’s birthday so were treated to some extra Sake shots in celebration, in addition to the 4 amazing sake’s that were served with our flight. At the end we were offered an add on (again, “optional”) A5 Wagyu topped with caviar, and it was an amazing finish to an incredible experience. 

Our dinner companions were all local and all agreed on a few spots we needed to add to our already full list. But who are we to pass up recommendations from locals.  We gladly shifted our schedule slightly, but first we had to get south to the Loop.

The Milk Room (The Loop)

We planned a little later reservation knowing we were coming from the west coast time zones and could possibly stay up a little past our bedtimes.  So, at 9:30 we found ourselves pulling up to the Chicago Athletic Association.  Inside the Athletic Association are a couple different bars and restaurants, a game room, and a drawing room, beautiful and elegantly done.  Then there is The Milk Room.  Slightly hidden (except for the velvet rope), on the second floor, the amazing stained-glass entrance is not marked, but you will see it.  You must have a reservation, because like the Sushi Suite, The Milk Room only has limited seating (eight seats), and reservations are hard to come by. 

It is easily the most beautiful speakeasy we have been to.  Given the history of Chicago, you know they really know the whole speakeasy vibe, but this is an actual former speakeasy.  The room maintains the prohibition-era feel, and their cocktails are very alcohol-forward, heavy, but incredibly well thought out.  These mixologists know what they are doing! They also specialize in vintage spirits and whiskies, so plan to up-level your palette.

ssn – The Milk Room was sexy! There was a “welcome drink” here – which we love – a champagne. The seating is interesting. You sit along the micro-bar but at a slightly lower level. So it has a private, intimate vibe. I did not need the romance with my sister, but you get the feeling.

Unfortunately, we were there just before closing, so one and done we decided we had to take our Sushi besties’ recommendations and headed back across the river to the River North District.

The Green Room/The Drifter (River North)

The Green Room Tavern is supposedly haunted.  Obviously, we were in for that.  It is also just two doors down from Mr. Beef (of The Bear fame), so obligatory photo op.  One of the only remaining wooden structures after the Great Chicago Fire (after the fire, wooden structures were forbidden).  The building has a slight lean to it, having settled into its frame in the post-fire rush to build (1872, if you’re not feeling like Googling).

In the times of Prohibition, the presence of a green door to an establishment indicated the location of a speakeasy.  After entering, go all the way through to the back, find the staircase, at the bottom of the staircase find the speakeasy.  In an effort to maintain the speakeasy vibe, we aren’t telling you where it is, but we did walk right by it our first time down the hallway. 

We got in without a reservation, but don’t bank on that.  There is a cover charge ($7), because there is also a burlesque show!  But first, let’s talk cocktails.  They have a rotating list of cocktails; they give out tarot cards that the cocktail is based on.  Each card is different and lists the name and ingredients on the cocktail.  Peggy had the Cabana Boy Blues on the Three of Swords, I had the Duggan’s Demise on The Fool.  I won because mine came with a fudge stripe cookie (once, again, foiled by gluten in a cocktail, but survived).

Then there was a burlesque show.  Fun vibe, just one performance then a break for 30 minutes until the next performance.  But the whole vibe was fun, and we are glad we fit this one in.

Speakeasy Fairy Godmothers

ssn – on our way out, as we were heading upstairs, we ran into a cute boy who looked lost. He heard there was a speakeasy but couldn’t find it. We took it upon ourselves to help. We imparted our knowledge upon him and gave ourselves the new titles of Speakeasy Fairy Godmothers. He wanted us to come up and meet his friends. They were there for a bachelor party weekend but there were only 3 of them; sweet, very young and wanted us to keep in touch throughout the weekend to let them know how the other bars turned out. Too cute.

Still perplexed as to how we were so tipsy, we did have to recall that we had (multiple) sake shots with our sake flight.  This seemed like a good time to test our new TikTok anti-hangover remedy and prepare for the next night!

ssn – Patti was perplexed because she must have forgotten a stop at the Sparrow, which I have still mistakenly been calling the Swallow (hahaha) before going back to the hotel. This was another recommendation from the Sushi friends and echoed by the bartender at Milk Room. It was beautiful and we had one final cocktail although it was a bit hazy!

Violet Hour (Wicker Park)

Violet Hour was listed as a “High Priority” for us, as it made the list of America’s Best Bars and is a James Beard award winner for their bar program. 

It is found in Wicker Park.  It shows up on the Goog for the address, but when you get there, you only see a big mural on a cement wall.  Look for the handle, because there is a door blended into the mural. Head in, there is a hostess stand at the end of a hallway, and she will lead you behind the curtain into the speakeasy itself.

For the experience itself, we are still left feeling kinda of “huh?”.  I should have known when we walked by a table with two ladies who were all but glaring at us that this wasn’t our place.  We did not hate it, it just never felt “right”. The room was stark, with no art on the walls, with high ceilings, and high back chairs around cocktail tables facing each other in rows.  It was a little isolating and not open feeling. The bar, however, was beautiful.  And instead of those annoying high, uncomfortable, metal bar stools, they had these low, wide, comfy looking padded stools. They were amazing looking. 

Violet Hour – The Drinks

They had weird drinks, but they all had really cool names that make you want to work your way through the menu.  I had the dragon lady fire drink.  Which, naturally, came set on fire, but also in a ceramic Tiki-style dragon cup. You know I love that!  Peggy had the Taylor Swift inspired I’m the Problem (Gin, Malort, elderflower, grapefruit) her wheelhouse.  Drinks were great and I wish we could have tried a whole lot more like the Matthew Bacconnaughey or the Bite it Eve.  However, we had multiple stops still to make and a desire to remember them all.

ssn – we wanted to love Violet Hour! It is ranked so highly on every list we looked at. I think it was that the build-up and expectation were just so high. It checks all the boxes (and the drinks were fabulous!) but there was no WOW. Even looking back at the pictures, it feels like one of those temporary restaurants they set up on Top Chef for a competition. Would definitely love to hear what you think!

Dorians (Wicker Park)

Right around the corner from The Violet Hour, Dorians fronts as a record store.  Just look for the “Listening Room” sign, show the cashier your ID, and into the back room you go.

We absolutely loved the stage and wished we were there for a show, but also the walls were stacked with shelves upon shelves of Vinyl.  It was super cool.  A hint of dive bar, but also the feel like you’d just discovered some underground classic club. The cocktail list is short, but something for everyone.  A little Mr. Demeanor and a Big Papa, with a little snack of labneh and pita chips and we were sad to already be leaving as their drink special was the Gayspresso and a Pride Night followed.

A reservation at Kings Cup and a Tarot card reading were the highlight in between Dorians and Gatsby, but that will be discussed in our day drinking blog post (coming soon).

Gatsby (Lincoln Park)

This, I have to say, got incredibly high marks from us.  Although there is a sign for The Gatsby out on the street, it is located inside the Bourgeois Pig cafe. When you check in at the front desk, the most adorable woman greets you and gives you a piece of paper with riddle to solve and send you upstairs to figure out how to gain entrance based on the riddle.  Best entrance of our entire trip.

So, up the stairs we go.  Long hallway, a little room with a bookcase, and we solved the riddle pretty quickly (won’t tell you what it was, but it’s clever), a little light goes off inside the bar and were let into the speakeasy.

And it was perfect inside.  The theme was well executed with a 1920’s feel to the décor without being the dark, drabness that some speakeasies can feel like.  Interesting artwork, a big wooden bar as you walk in, and then a series of rooms wrapping around the layout for a cozier feel, plus a big library room towards the back.

They were super busy, and service was slow, but they were great about it.  Apologies from Nora for the delay, she was awesome, they were friendly and did their best to cover a bar full of people while they were shorthanded.

Drinks were all Alice in Wonderland themed. All 5 of them.  I had the Drink Me, which came with a little “drink me” tag hanging out of the glass. Peggy had the Cheshire Grin which had a Cheshire cat style stripe through the foam and come to find out the base was Malort, that disgusting Chicago local favorite spirit – and it was delicious.

A Little Chicago-style Sisbehaving

Six Drinks into the night and the fun escalated.

When we realized that the alley where John Dillinger was shot was only 2 blocks away from Gatsby.  Peggy needed to see it. And apparently, recreate it.

We decided we needed late night sushi, because that’s just who we are.  Late night sushi is second only to late night Korean BBQ, and there was an Izakaya back up the road near King’s Cup.

And that’s when the magic happened.  The homeless guy hanging outside the liquor store offered to buy our panties.

There’s a first time for everything.

And in hindsight, we should have found out what the starting bid was, I mean what if he wasn’t actually homeless and was simply an eccentric billionaire who was testing us.  He could have been Peggy’s new sugar daddy.

But I guess now we will never know.

The Alderman (Pilsen)

I feel like I keep listing everything as our favorite. But our time at The Alderman was absolutely fantastic.

First the entrance: Inside the Pilsen Yards, which is a great Mexican restaurant with a big outdoor patio in the Pilsen neighborhood. There is a door simply marked The Alderman (in not so simple neon).  So, while not exactly hidden, you must know it’s there to know to go in.

The Alderman is a lot more upscale than the outside lets on.  It has a dark and masculine feel, with seating for only 16 and a well-thought-out drink menu curated by the bartenders themselves with a mix of weird, exotic, and classic ingredients.

AND there was a welcome drink. And you know we are a sucker for a welcome drink.

For us, what made it so outstanding was the service.  Our reservations were for bar seating (our preference), where we were greeted by bartenders Matt and Sven. We found out it was Matt’s last day at The Alderman.  We had great conversation, got to ask lots of questions about the bar and the drinks, did group shots with Matt and Sven, and listened to Matt’s plans for the future.  It was like we were regulars from the moment we walked in the door. This was right before our Stevie Nicks/Billy Joel concert, and they were genuinely excited for us. 

The Alderman – The Drinks

They have a fantastic selection of alcohol and we were lucky to try some barrel-aged rare rum, and an amazing whiskey selected by the bartenders, and hear Matt’s wealth of knowledge (as he was the one who had picked out these selections for the bar).

We hope Matt is doing well in school, and that his replacement fell right into the big shoes he had to fill (and no, I don’t want to name him, just in case he didn’t last the night, such a cute little boy, nice but young and inexperienced).

ssn – The Alderman was my favorite of the trip. In honor of our concert, Sven asked, “If Billy Joel wanted a shot, what would he want?”, and proceeded to create something for us. So fun!

The Blind Barber (Fulton Market)

Barber shop by day, speakeasy by night.  This was a last-minute squeeze-in while we were waiting for our later reservations.  Luckily it was close by in Fulton Market.

It’s an actual working barber shop in the front.  The receptionist quickly identified that we were not there for a cut or shave and opened the unmarked door in the back wall, not hidden but looks like it should be an office door or janitor’s closet. Little hallway opens up to a fantastically almost 70’s vibe speakeasy.  Wood paneling, long booths along the wall, wood bar, dark moody. As Peggy said it’s almost like they tried to do Tiki, but gave up and settled for 70’s.  But not Good Night, John Boy tacky, disco 70’s, more your parents rumpus room 70’s. Oh, and a DJ booth in the back, so giving hip night life feelings.

Great drink menu, couple of locals hanging out, espresso martini “thinking shots” and a little conversation with the bartender.  It was a quick hit, definitely want to stop in for a cocktail, and to check the box on your speakeasy tour.

ssn – “Thinking shots” is new term we have coined. When you can’t choose from the menu, you have a little shot to tide you over and get the decision process moving. Not sure at what point we named it, but it stuck.

The Booze Box (Fulton Market)

And then a happy little accident occurred!  We were going to check out Gin Alley in Fulton Market, because the pictures looked so cute.  We walk by an alley and spot a lighted red arrow pointing towards a doorway. 

YAY, Surprise hidden bar signal.  They only had a sign on the door with hours, but nothing else saying anything about what it was.  We had to kill a little time before opening, but we were right there when they did.

Turns out Sushi Dokku on the corner has a little bar downstairs.  We discovered the hidden staircase, but others used the restaurant entrance.  So more of a “hidden bar” than a true speakeasy. Very Japanese feel, obviously, given the upstairs sushi bar, and you know my Japonessa sister was loving it. 

It was dark, there were big shelves over the bar filled with Japanese labels, red paper lanterns, and round booths lining the back wall.  We lucked into a bar seat where I had probably my favorite drink of the entire trip, The Murasaki:  Rum, egg whites, lime, and ube syrup. I have zero idea what Peggy had because I was wrapped up in my own little foamy, purply world.

We were very sad that we were still full from late lunch at Au Cheval, so no food was ordered and that was a complete failure for us.

ssn – she’s right, I love my Asian bars and this was such a fun find. We found it without even trying and didn’t realize until writing this post that it was on our list all along.

The Office

Hidden through a back hallway and down a staircase, The Office sits below The Aviary, a restaurant concept of the Alinea Group (Grant Achatz for your food nerds).  The Aviary looked amazing, their drinks looked fun and amazing, and the food made us want to rethink walking down that hallway.

But we did.

Dark elegance behind a locked door, interesting artwork, Persian style rugs, thoughtful knick-knacks, and walls and cabinets full of dusty bottles with plain tags listing the name, year, and price. 

Just about 6 bar seats at a small bar, and then a room full of sitting areas with couches, love seats, old parlor chairs.  At the bar we are handed a thick, leather-bound book full of insanely old alcohols, with old, like over a century old, spirits, with full descriptions and background of the bottle, and a whole lot of expensive prices.  And suddenly we become very aware of our limited means in this place. 

ssn – Did anyone else just hear Ron Burgundy enter the conversation?  “I’m very important. I have many leather-bound books and my apartment smells of rich mahogany.”

However, the bartender will make you anything you wish, or you can tell him your likes and dislikes and he will curate a cocktail for you.

The Office – The Drinks

I had a peach cocktail that utilized “Good Vodka”, as in that’s the brand name of it.  A friend of the bartender started a distillery using discarded coffee fruit, so we even got a really cool story to go with it.  The bartender did engage us with the background that the owners actually seek out vintage bottles of alcohol at auctions around the country, looking for old, unique, and not seen in decades bottles found in basements and broken down sheds.

Our pre-paid reservation came with a single bite appetizer, we chose the Black Truffle Explosion. This one absolutely my best bite of the year (for the first 6 months, that is).  I’m not even sure how to explain this ravioli topped with black truffle and parmesan, when you bite into it the ravioli breaks open and fills your mouth with the black truffle juice and butter – absolutely amazing (for more information on this, see the Grant Achatz “Chef’s Table”, Season 2, Episode 1).

We hung out long enough to order a second round of drinks, when the chef from The Aviary came down to check with the bartenders about limited orders for his new truffle grilled cheese, and we were in for trying that. 

The Office is very upscale, so if that is your style The Office is for you.  It is definitely not one of those loud, outlandish bars, the simplicity and elegance speaks for itself, but bring a full wallet, as I said the specialties can get a little spendy (there are whiskeys that go for $625 an ounce) and there might be something exquisite you need to try.

The Office served as the perfect ending to our speakeasy tour of Chicago.

Other Chicago Speakeasy recommendations

ssn – Let me endnote this post by telling you about the immense amount of research that went into this trip. Since Chicago is basically home of the Speakeasy, the options were staggering. We started with a list of more than one full hand-written page, compiled from various articles with their rankings:
Thrillist, How to Get Into Chicago’s Best Speakeasies and Secret Bars
Time Out, The Best Chicago Speakeasy Bars to Discover
The Infatuation, 10 Great Hidden Bars & Speakeasies in Chicago
and added from there from things we saw on social media.

We added every one to our Google Map, researched each one, and had to narrow them down to the most important and intriguing, by neighborhood, by opening days and hours. Tough job but somebody had to do it. Also, we recommend reservations at all of these (where available)

Here are a few that we just could not get to (yet!) that were high on our list: Nine Bar (Chinatown), The Library at Gilt Bar (River North), The Bamboo Room (inside Three Dots & a Dash)(River North), Valedor (Wicker Park), Untitled Supper Club (River North). And of course, everyone’s social media favorite is the Chicago Magic Lounge (where you enter through the Laundromat), we probably won’t be covering that – but never say never!

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