Chicago

Chicago’s Best Hotel Bars Have Impeccable Cocktails and Vibes

Chicago's hotel bar scene is one of the country's very finest.

Photo courtesy of Freehand Chicago
Photo courtesy of Freehand Chicago
Photo courtesy of Freehand Chicago

It’s a story as old as the city itself: Back when railroads were all the rage-i.e., the mid- to late-19th century-Chicago, fresh off 1871’s devastating fire, rose to prominence as America’s number one transit hub. Thanks to competing lines, it was impossible for an East Coaster to make their way west without changing trains, and vice-versa. And as a centrally located industrial powerhouse with an already thriving freight presence, Chicago was a natural place for passengers to transfer from one line to the other. There was a catch, however: Schedules didn’t often align perfectly, forcing many travelers to spend their overnight layovers exploring the Windy City. And Chicago’s rapidly expanding assortment of hotels were more than happy to meet their needs.

Of course, with those hotels came restaurants and, more importantly, bars. These drinking emporiums mirrored the opulence of their surroundings, designed to woo out-of-towners while also catering to the local moneyed classes. Today, despite both Prohibition’s and the aviation boom’s best efforts, Chicago’s hotel bar scene is still one of the country’s very finest, with options ranging from laid-back lounges with a view to age-old gems with Gilded Age-style flair. Here are the best of the best.

Photo courtesy of Freehand Chicago
Photo courtesy of Freehand Chicago
Photo courtesy of Freehand Chicago

Broken Shaker

River North
Stashed away on the first floor of the always-bumping Freehand Chicago, iconic Broken Shaker does things a little bit differently. The space-dimly lit, cavernous, and cloaked in quirky nautical artwork-evokes a chilled out ‚Äė70s vibe while a rotating cast of top-notch DJs spin vinyl for travelers and locals mingling on plush couches. And then, of course, there are drinks: thoughtful combos that skillfully play on classics like the paloma-esque So Fres$h & So Clean (Tromba Blanco tequila, Joseph Cartron Pamplemousse Rose, agave, lime, and acid solution) and the breakfast-ready Noah’s Old Fashioned (Reese’s Puffs cereal-infused Smooth Ambler bourbon, Angostura bitters, orange bitters, demerara). Hungry? Why wait-the kitchen has your back with satisfying bar bites like tacos, fried chicken sandwiches, elote, burrata with heirloom tomatoes, and mini churros.

IO Godfrey Rooftop Lounge

River North
Equipped with a clever retractable roof for year-round vibing, this River North fixture stands tall as the city’s largest rooftop bar. To complement its solid beverage program (see: Scarlet Haze, a delectable mix of Del Maguey Vida Mezcal, Cointreau, sour cherry, and black sea salt) and equally enticing pan-Asian cuisine, the bar hosts a never-ending lineup of fun-in-the-sun (or -snow) activities and events like an immersive haunted experience for Halloween and heated igloos come winter.

ROOF on theWit

Loop
This visually stunning 7,000-square-foot respite soars 27 stories above the earth. But it’s not just size that matters here. There’s also textured walls studded with artfully arranged flatscreens, verdant greenery, retractable walls, a gorgeous Deco-inspired back bar, and a host of refreshing cocktails and tasty shareables. All that plus bottle service and plenty of room for raucous DJ- and live music-fueled dance parties-what’s not to like?

Cindy's Rooftop
Cindy’s Rooftop
Cindy’s Rooftop

Cindy’s Rooftop

Loop
The literal crown jewel of the recently renovated Chicago Athletic Association not only offers some of the best views of Millennium Park, it also shakes up some of the area’s finest cocktails for both indoor and outdoor consumption. The multi-page menu is a treat in itself, listing cheekily titled tipples like Raspberry Beret (Rittenhouse rye, Lustau oloroso sherry, raspberry, hibiscus, lemon) and Fernet About It (Beefeater gin, Fernet, lemon, strawberry ginger rosemary syrup, soda) alongside colorful little illustrations. As for food, brunch is big business in these parts, when hearty best-sellers like chorizo-laden chilaquiles, rich biscuits and gravy, and chicken and waffles take center stage.

The Lobby Bar at Lockwood 

Loop
Welcome to one of Chicago’s most ornate bars, where cathedral-like frescoed ceilings and towering marble columns surround a sparkling little bar stocked with unbeatable classics and seasonal twists (don’t sleep on the dangerously smooth 187 Whisky Sazerac). If you can’t make it to church on Sunday, it turns out the stately Palmer House Hotel is a perfectly acceptable alternative.

Milk Room

Loop
Over the years, beloved restaurant and design firm Land and Sea Dept. has left their mark on Chicago in many different ways-but no other concept quite compares to this diminutive cocktail den hidden within the Chicago Athletic Association’s second floor. Here, those lucky enough to have scored a seat (there are only eight of them) will find a treasure trove of rare and vintage spirits served on their own or stirred into exquisitely executed cocktails by the extremely knowledgeable staff. It’s no wonder the handsome outfit bears so many accolades, from local best bar nods to national rankings by Esquire and this year’s World’s 50 Best Bars.

Alma
Alma
Alma

Alma

Wrigleyville
If you thought Wrigleyville was all frat boys and sports bars, you wouldn’t exactly be wrong. But this sprawling lounge inside the Zachary Hotel is the polished exception to the norm-while still paying homage to its ballplayer roots. Fully revamped in June, 2023, it’s already proven itself a quality hangout, providing Northsiders with a wall of windows facing the Friendly Confines, plush mid-century modern decor, a glowing brick fireplace, historic photos, and a tastefully placed DJ booth primed for weekly vinyl nights. And to drink? Expect original concoctions brimming with proprietary booze like an Old Fashioned with Hotel Zachary Sherry Cask Jeppson’s bourbon and a house bitters blend, plus mini-flights for the cocktail-curious, frozen drinks, and a coveted Suntory Highball Machine (aka Japanese whisky sodas on tap).

Clever Coyote

Wicker Park
This new-like brand new-second-floor hangout inside The Robey’s 1929 landmarked building has hit the ground running with a neon-lit ‚Äė90s throwback theme imbued with more Millennial nostalgia than an Alanis Morisette cover band. But don’t worry, you won’t find any Pop-Tarts and Snackwell cookies around here. Instead, the cocktail menu leans into tropical flavors, featuring kitschy headliners like the activated charcoal-spiked and agave-driven Black Hole Sun and Sucker Punch, a clarified gin milk punch topped off with a Spice Girls-endorsed lollipop.

Lazy Bird

Fulton Market
A charming mid-century aesthetic, deep circular booths, long marble bar, and 52 different cocktails converge to make this Fulton Market hideaway inside the interminably hip Hoxton Hotel one of the best in the business. Come for a laid-back evening sip before snagging a table upstairs at Cabra, or stop by for a couple of late-night libations accompanied by live music and a surprisingly clubby atmosphere on the weekend.

Bar Pendry

Loop
Posh cocktails and an eye-catching interior design beckon the swanky set into this operation inside the Pendry’s stunningly refurbished 1929 Art Deco Carbide & Carbon building. Select small bites play a supporting role to a perfectly balanced cast of cocktails where contemporary takes like the Crimson and Carbide (mezcal, lemon, beets, ghost pepper agave) square off with expertly made classics. And while the drinks are top notch, Bar Pendry really pulls with its library-meets-date night vibes, sporting a double-sided fireplace, butter-soft leather couches, and rich wood paneling.

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Meredith Heil is the Editorial Director of Thrillist Travel. Follow along with @mereditto.

Jay Gentile is a Thrillist contributor. Follow him:@innerviewmag.

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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