Chicago

The Best Cocktail Bars in Chicago

MONEYGUN
MONEYGUN
MONEYGUN

There was a time in this town when a fancy drink consisted of anything that wasn’t made in a bathtub. Well, times have changed, Sonny, as evidenced by the decreased occurrence of devastating fires started by cows and the vast improvement in the quality of our fine spirits. Don’t believe us? Well, perhaps you should visit one of the best cocktail bars in Chicago and stir up a conversation.
MORE: Don’t drink on an empty stomach. Stop by one of the best restaurants in Chicago.

LEIGH LOFTUS
LEIGH LOFTUS
LEIGH LOFTUS

The Berkshire Room

River NorthWith its cloud-scraping ceiling and checkered Alice in Wonderland floor, this boutique-hotel bar seems much bigger than it really is. Yet, once you take a peek around, the bar feels quite comfy, and the cocktails here have a similar ability to defy expectations. Sure, you’ll find a nice selection of local spirits and inventive drinks, but the real magic happens when you order a Dealer’s Choice cocktail. You’ll pick a spirit (such as aquavit or mezcal), flavor profile (smoky, spicy, etc.), and glassware (a Collins glass, etc.), and *poof* a unique cocktail made specifically for you appears.¬†

ANTHONY TAHLIER
ANTHONY TAHLIER
ANTHONY TAHLIER

Drumbar

StreetervilleSimply put, Drumbar is stunning. This may lead some to believe that it’s the perfect spot for unfettered Instagramming and throwing back rooftop mimosas like they’re vicious slam dunks. On the contrary, Drumbar makes some of the best cocktails in town, and any visit that includes top-of-the-line seasonal cocktails and an epic lounge sesh in a tufted-leather sofa is really where the action is. Choose from specialty cocktails like the Nouveau Negroni or four types of Old Fashioneds in a sexy speakeasy-styled drinking den on the 18th floor of the Raffaello Hotel.¬†

COURTESY OF THE WHISTLER
COURTESY OF THE WHISTLER
COURTESY OF THE WHISTLER

The Whistler

Logan SquareYears before seemingly every neighborhood on the North Side had its own cocktail joint, the Whistler was drawing crowds to an unexciting stretch of Milwaukee Ave mostly devoid of bars. Fabled mixologist Paul McGee spent three-and-a-half years whipping up drinks here, but the bar is still going strong long after his departure. Patrons keep coming back for the live music and surprisingly affordable drinks, which range from $7 to $12, and seem like a downright steal when compared to some of the pricier options around town. The Whistler helped the craft-cocktail movement bloom in Chicago, but it hasn’t aged one bit. While you’re here, check out the rotating art installations, film screenings, and “movieokie“.

Courtesy of The Sixth
Courtesy of The Sixth
Courtesy of The Sixth

The Sixth

Lincoln SquareKick back with a good drink at The Sixth, and you may start spacing out enough to think you’re currently in a Downtown lounge. Yet, the lack of pretension here will quickly snap you back to reality, because for all its spirits-mixing wizardry, The Sixth still has the soul of a buttoned-down neighborhood bar. Knock back cocktails of modern mixology mastery made with specialty ice such as the S’more de Amor dressed with Mexican chocolate and marshmallow foam and the Weston, which contains ingredients such as bourbon, Dark Matter coffee, and pipe tobacco (add a dram of chocolate CBD for extra kick). Both are mesmerizing.

CLAYTON HAUCK
CLAYTON HAUCK
CLAYTON HAUCK

Milk Room

The LoopUpon first glance, Milk Room just seems like too much fuss, hidden away in a small section of the Chicago Athletic Association’s second floor. The bar has only eight seats, the drinks cost upwards of $50 each, and in order to visit, customers have to book a reservation through Resy. For the masses, going through all this hassle is, as you can imagine, quite unimaginable. Yet, it’s worth it if you have a taste for the uncommon, because the bar stocks spirits that are, in some cases, not even replaceable. Drinks are made with decades-old bottles that have been acquired at estate sales and such, allowing cocktails to transport patrons back through time. For some, that’s priceless.

CLAYTON HAUCK
CLAYTON HAUCK
CLAYTON HAUCK

Lost Lake

Logan SquareFor mixologist Paul McGee, the hits seem to keep on coming. Aside from finding success at the Whistler, Three Dots and a Dash, and Milk Room, McGee has sprinkled some of his buzz-baiting pixie dust on Lost Lake. The charming tiki bar provides plenty of colorful drinks, rum bottles, and shareable bowls. But what really stands out, besides the quality of the drinks, is just how much fun everyone is having. Named “Best American Cocktail Bar” by Tales of the Cocktail in 2018, the endlessly name-checked bar also serves late-night Chinese-American eats that pair alarmingly well with cocktails in volcano bowls.

Freehand Chicago
Freehand Chicago
Freehand Chicago

Broken Shaker

River NorthSurely two of the finest cocktail bars in Chicago cannot be located next door to each other, right? Alas, they are, and you should visit them en route to Truth, Meaning, and a great buzz. The Broken Shaker has some serious competition next door at the Berkshire Room. Yet, that has only elevated its game, as evidenced by wonderful cocktails such as the Potato Chip Old Fashioned or the carrot juice-infused Whatever Happened to Carrot Top.

The Aviary
The Aviary
The Aviary

The Aviary

West LoopThe Aviary is the kind of spot where you’ll always be worried whether you’re underdressed, and the drinks cost about $5 more than you’re used to. Regardless, the cocktails here verge on the fantastical, assaulting the senses with unfamiliar smells, shapes, flavors, and colors. Smoke, booze-filled ice spheres, ship bottles — the Aviary has been known to serve them all with cocktails and does not give an eff. It’s the cocktail equivalent of seeing Fury Road in 3D: not everyone’s cup of tea, but mind-blowing nonetheless. Drinks are designed as works of art at this high-end cocktail laboratory, and the ethos continues at hyper exclusive basement speakeasy The Office.

FLICKR/STAR5112
FLICKR/STAR5112
FLICKR/STAR5112

The Violet Hour

Wicker ParkThe Violet Hour is built on a foundation of confidence. It’s dark, hushed, and does not care for cell phones. Its fa√ßade is a mural-covered wall, and the draped interior shrouds the space to such an extent that it’s difficult to tell just how big the lounge is. Hell, the bar even made its own Mal√∂rt. Yet, the seasonal cocktail menu is dependably impressive, and people still line up to grab a seat during peak times at this Chicago classic. Locate the entrance from the door handle hidden inside the exterior mural on Damen and nerd out on their James Beard Award-winning bar program.

COURTESY OF SCOFFLAW
COURTESY OF SCOFFLAW
COURTESY OF SCOFFLAW

Scofflaw

Logan SquareScofflaw may be one of the best-loved bars in all of Chicago. It has plenty of critical accolades, and loyal patrons swear by this neighborhood spot and its excellent, reasonably priced cocktails. Sure, Scofflaw’s classification as a gin-centric bar is a bit overblown, but that’s because it carries tons of other spirits and prepares them equally as well. But, yes, you should order anything made with their handcrafted Old Tom gin, and stick around until midnight, when the kitchen hands out free fresh-baked cookies, and then sip drinks like the bourbon-based Sea Quake and the mezcal-infused Hearth Tax by the fireplace in their Victorian-style “salon” room.

Billy Sunday
Billy Sunday
Billy Sunday

Billy Sunday

Logan SquareArmed with a deep library of vintage spirits and a cocktail menu that takes a culinary approach to flavor, Billy Sunday is more than just “another cool Logan Square cocktail bar.” It’s a central gathering place for those in the cocktail know, or curious newbies looking to up their collegiate rum-and-Coke/Red Bull vodka mixology game. Here you’ll find draft cocktails like the Americano, seasonal delights like the whiskey and tea-infused Backhanded Compliment, and vintage classics like the Sazerac and Rusty Nail. There’s also a small but well curated beer list with local offerings from Marz and others, which you may feel free to pair with bar bites like meat boards and sweet potato cakes. Check out the back bar for one of North America’s largest collections or Fernet and Amaro.

MONEYGUN
MONEYGUN
MONEYGUN

Moneygun

Fulton MarketThis low-key yet fun hang from the folks behind Longman & Eagle, Empty Bottle, Thalia Hall etc. declares itself as “just a bar” — and the understated sentiment is pretty hard to argue with. The place is just cool without trying too hard, as evidenced by a solid menu of classic cocktails without all the BS and Instagram-obsessed fuss. Order from the selection of their expertly crafted “40 Essentials” cocktail menu with offerings like White Russians, Hurricanes, and Manhattans before checking out some of their obscure brews like Boulder Shake Chocolate Porter and Collective Arts Guava Gose. Finish the night with some bar snacks like their “Moneynugz” house-made chicken nuggets, tater tots, and skewers — and if you’re still hungry, head next door to sister restaurant Saint Lou’s Assembly for some diner-styled goodness. Be sure to hit up their giant shared back patio in the summer.

The Drifter Chicago
The Drifter Chicago
The Drifter Chicago

The Drifter

River NorthOne of the most unique drinking destinations in Chicago is this oddball speakeasy with an eye towards the occult located in the basement of the historic Green Door Tavern, one of Chicago’s oldest bars. The place isn’t trying to be a speakeasy, because it was an actual speakeasy during actual Prohibition. The tiny space maxes out at a capacity of 37, but there may be no better date night bar in the city. Once inside, navigate the daily-changing menu of more than 100 cocktails presented on tarot cards as you look forward to strange performances ranging from burlesque to music to pop-up variety acts. The drinks are good, yes, but the environment is even better.

The Heavy Feather
The Heavy Feather
The Heavy Feather

Heavy Feather

Logan SquareSlippery Slope is well known as one of the rowdiest party spots in the city. But what is less well known is that after you’ve had your fill of late-night drunk dancing, drunk Skee-Ball, and cheap beer at Slippery Slope, you can head upstairs for an entirely different vibe at the ‚Äė70s-styled “fern bar” that is Heavy Feather. We’re not sure what the hell that means, but we are sure the drinks are damn near perfect. Cozy up in a comfy booth where you can actually hear the other person talk and sample a dizzying array of standout libations from the mezcal and tequila-infused Midas Touch to the milkshake-styled Comfy Chair made with cognac, white rum, eggnog, and vanilla ice cream. Don’t worry: They’ll save room for you on the dance floor downstairs.Sign up here for our daily Chicago email and be the first to get all the food/drink/fun in town.

Raf Miastkowski loves a great cocktail, but is not ashamed about living the High Life. Send a drink @RafFoSho.

Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile

Chicago

Robyn DaCultyre Is Doing It for the Culture

"The cool thing about Ohio is that there is literally a place for everyone."

Photo by Kayode Omoyosi
Photo by Kayode Omoyosi
Photo by Kayode Omoyosi

I was introduced to Robyn DaCultyre at an Untitled Queen show at C’mon Everybody in late January, and it was one of the most unique drag shows I’d seen in a while. Afterwards, I tracked down this self-described “drag creature” and video chatted about her drag origin story, the state of drag in her native Ohio, and the dual identities that make up her persona. Thrillist: I want to ask you about how Robyn DaCultyre came about and your point of view behind your performance.

Robyn DaCultyre: I’ve been travelling around the country from a young age in ministry and Christian studies. I moved to Chicago right after high school. Four years later, moved back to Columbus and decided I didn’t really want to do church anymore; that wasn’t where my heart was.

I had a really low point in my life and had a suicide attempt and then really found drag and started doing drag as a coping mechanism and way to let off steam. I started in July of 2019, and it was really a lot of punk and metal music. I created this drag creature of sorts and they were really out of this world and celestial and all of those fun alien type terms.

And then we went into a global pandemic and I had a lot of time to figure out who I wanted to be. Digitally I was still doing a lot of drag creature-esque numbers and all of that, but I had this moment where we’re on the front lines getting hit with pepper spray and rubber bullets and pepper spray-all of those lovely things. And I said, I have this platform and I need to start showcasing what’s happening.

Untitled [Queen] stepped in at the right time and messaged me and said, “I’m doing this show for Independence Day called Untitled in America with 52 different performers and I want you to be a part of it.” It was at that moment I was able to take the footage I had been recording on the front lines and incorporate it into digital content. I did a song called Black Like Me by Mickey Guyton that talks about white picket fences, but if you want to see how America is, then you should try being Black like me. The imagery of what’s literally happening in Columbus in that digital performance really spearheaded me into focusing on people who look like me.

Nina Simone is one of my biggest inspirations, and one of her quotes that resonates with me is that it’s the duty of the artist to resonate with the times. My art is politically charged. I like to entertain, but there will definitely be a time when you come to a show expecting to have your drink and be chill and that might not be the case.

How did the name Robyn DaCultyre come about?

I was smoking with Ursula Major, who was on season one of Dragula, and the first time I introduced myself to her I was Robyn Banks, which is my drag name originally. She said, “Well, do you just not want to be original at all?” [Laughs] And I sat with that for a couple of months, and I got really stoned one day and was listening to Janelle Monae, and she talks about doing it for the culture, and I said “I do it for the culture, too!” And the rest is history.

And you started a series called Melanated.

We started Melanated last February. I told the idea to my show director that there were no shows specifically run by Black people that only featured Black entertainers. I wanted to do this show for a night and she said, Why don’t we do it once a week for the whole month? The first show happens, and it’s a sold out crowd, and [my director] comes back and says we should do this every month. So I sucked it up and here we are a year later.

Melanated is the only fully Black show in all of the state. It’s a horrible marketing tool and not something I want to promote, but it is just a fact. It amazes me that we are the 13th largest city in America and there’s nothing here that’s fully focused on Black entertainers. The name also comes from Janelle Monae; she says she’s highly melanated and I said, that works.

Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)

You refer to yourself as a drag creature, as opposed to drag queen or king…

This is actually the first time I’m making this public. I am in this place where I want to separate the alternative creature from who this melanated goddess or whatever is. DaCultyre is definitely the person who runs Melanated and then Robyn is this drag creature that is out of this world and really loves punk and alternative music. And both intertwine to make Robyn DaCultyre.

You also do pageants. Tell me about that.

In 2020 I was appointed by Nina West, who is from Columbus, as the representative from Ohio for National Entertainer of the Year in Louisville, Kentucky. I placed ninth out of 13 contestants and I really fell in love with the system and fell in love with the pageantry and loved the idea of reigning and being different. I want to show that we as alternative performers, as bearded performers, you can come into these systems and shake things up.

Is there a uniquely “Ohio” style of drag?

No, and I think that’s one of the things that makes it so amazing is that everyone has their own unique style, and it’s all pretty much accepted. I started as a performer and a drag creature and there was space that was afforded to me and I transitioned to more glamor and pageantry and that’s afforded to me as well. I’ve been a bearded entertainer for a year now. The cool thing about Ohio is that there is literally a place for everyone.

I think I have everything I need. Is there anything else I didn’t ask you about that you want to bring up, or‚Ķ

I don’t think so. Are there any generic questions you haven’t asked?

Generic questions‚ĶI think I asked all of them already [laughs]. I like to ask what you’d be doing if you weren’t doing drag?

It’s a great question. I have a day job that is very demanding so I need drag to get away. I’m also very creative and artistic. I used to do web design and all these other things to pull into my creativity. Drag is the longest thing I’ve stuck with in all parts of my life, so I don’t think it’s going anywhere anytime soon.

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John deBary¬†is a drinks expert and writer. His first cocktail book,¬†Drink What You Want, is available now, and his next book,¬†Saved by the Bellini, is expected in early 2023. He is also the co-founder and president of the¬†Restaurant Workers’ Community Foundation, which is dedicated to improving the lives of hospitality industry professionals through advocacy, grant making, and impact investing.

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