Chicago

The Most Essential Rooftop Bars in Chicago

Sky's the limit.

Utopian Tailgate
Utopian Tailgate
Utopian Tailgate

There’s little we look forward to more in Chicago than rooftop season, and who could blame us? Sweeping city views and stellar food and drink are a match made in skyline heaven, not to mention one that’s hard-earned (remember January?). And with this town’s bounty of soaring drinking dens, we’re revved up to once again hit play on the outdoor imbibing itinerary-so long as a few other things stay in play, too (i.e. plenty of continued COVID-19 precautions). From margaritas in Logan Square and breezy West Loop brunch emporiums to music-fueled lounges in River North and the return of fan-favorite Cindy’s, here are Chicago’s best rooftop bars to visit right now.

Photo by Anthony Tahlier
Photo by Anthony Tahlier
Photo by Anthony Tahlier

Cabra

West Loop
Stephanie Izard strikes again with this skyhigh haven, found atop the tony Hoxton Hotel. The menu pays homage to the lauded chef’s memories of traveling around Peru, as emphasized by two house favorites: anticuchos (marinated meats grilled over flames) and ceviches (a nod to Izard’s time in Lima). Pair them with drinks that are just as wanderlust-inducing, such as the Malambo No. 5 with rum, lemongrass, and passionfruit, or the Pink Dolphin, a vibrant and aromatic mix of gin, hibiscus, and allspice.
How to book: Reserve via OpenTable.

Photo courtesy of Park Hyatt
Photo courtesy of Park Hyatt
Photo courtesy of Park Hyatt

NoMI Garden

Streeterville
Leave the scurry of Streeterville behind and venture up to this rooftop escape, where lush greenery and lakeside breezes await on the seventh floor of the sleek Park Hyatt. Settle in, then raise a glass-classic aperitifs like French 75s and Veneziano Spritzes hold their own against all the culinary elegance streaming out of chef Terence Zubieta’s kitchen, from seafood towers to prime striploin.
How to book: Reserve via Tock.

Photo courtesy of Nobu Chicago
Photo courtesy of Nobu Chicago
Photo courtesy of Nobu Chicago

Rooftop at Nobu

West Loop
Expect the same serene-chic aesthetic here that permeates the interior of this hotly anticipated hotel, which debuted last year with a dynamite team of backers (think: chef Nobu Matsuhisa, Robert DeNiro, and Meir Teper, to name a few). Kick things off with a round of sushi, of course, then move on to tempting bites like black cod miso or rock shrimp tempura alongside Asian-inspired drams like lychee-elderflower martinis and the Nobu Sidecar, a sultry concoction spiked with Japanese whisky and tart yuzu.
How to book: Reserve via OpenTable.

Photo courtesy of Cindy's Rooftop
Photo courtesy of Cindy’s Rooftop
Photo courtesy of Cindy’s Rooftop

Cindy’s Rooftop

Loop
Make a beeline to this rooftop for some of the most iconic views of the city-ones that capture postcard-ready panoramas of Millennium Park, Cloud Gate, Navy Pier, and miles upon miles of lakefront bliss. Breathe it all in with a side of the talented team’s boozy handiwork, namely the Mama’s Garden, an herbaceous coupe of gin, cucumber, basil, and lemon, or the Pudge’s Punch, a warming blend of rum, toasted sesame, and zesty lime.
How to book: Reserve via Resy.

Photo by Mistey Nguyen
Photo by Mistey Nguyen
Photo by Mistey Nguyen

Tanta

River North
Swing up to this River North rooftop for South American vibes and Peruvian plates that draw on a variety of culinary traditions from Japanese and Chinese to Spanish and Pan-African. Try the Cebiche Clasico, with leche de tigre, sweet potatoes, and choclo (large Peruvian corn kernels)-the ultimate accompaniment to all those pisco sours you’ll be downing. And don’t miss the nigiri pobre, a layering of rice, wagyu, and fried quail egg that serves as one of the city’s best dishes.
How to book: Reserve via OpenTable.

Photo by Kailley Lindman
Photo by Kailley Lindman
Photo by Kailley Lindman

Gibson’s Italia

Loop
Gibson’s fans were amped about this recent opening, an upscale Italian approach that employs the same quality and attention to detail as its sister steakhouses. And then, of course, there are the Chicago River views, made possible by two sprawling waterfront dining and drinking areas. Stick to the classics here with some of the team’s top tipples-we’re talking Manhattans and Old Fashioneds-and complement those sophisticated sippers with an order of seven-year-aged Acquerello Risotto (complete with scallops and baby leeks).
How to book: Reserve via SevenRooms.

Photo by Shannon Braniff
Photo by Shannon Braniff
Photo by Shannon Braniff

Upstairs at the Gwen

Loop
The digs are just as enticing as the menu inside this Loop-situated sanctuary, where guests are greeted by a locally painted mural and several fire pits ready to warm up even the chilliest spring eve. Take advantage of them during Movie Night Thursdays, your chance to check out classic films alongside a discounted cinema-inspired cocktail. When hunger strikes, opt for any of chef Matt Jergens’ crowd-pleasing plates, from grilled tzatziki wings to a house burger decked out with bacon and white cheddar.
How to book: Reserve via Tock.

Z Bar
Z Bar
Z Bar

Z Bar

River North
One of the most buzzworthy openings of recent years is this internationally-inspired stunner on the sixth floor of the Peninsula Chicago. The next time you’re looking to duck tourists, pop into this globally-curated hotspot for dishes like lamb meatballs and daikon frites paired with craft cocktails and a live DJ.
How to book: Reserve via Tock.

Aba Restaurant
Aba Restaurant
Aba Restaurant

Aba

Fulton Market
This 4,000-square-foot third-floor rooftop is stocked with posh seating, lush greenery, and fire pits that will have you sticking around far longer than you should. Soak up the scene as you dive into chef CJ Jacobson’s Mediterranean-inspired bill of short rib hummus, lamb ragu, and Jerusalem bagels paired with “ancient civilization” wines from Greece, Israel, and Lebanon plus killer cocktails from famed mixologist Liz Pierce.
How to book: Reserve via Tock.

Cerise Rooftop
Cerise Rooftop
Cerise Rooftop

Cerise

Loop
Keeping things cool on the 26th floor of the Virgin Hotel, Cerise’s posh flagship terrace wraps around a full three sides of the landmark building. With rotating DJ sets on Fridays and Saturdays, this casual chic space brings a slice of LA to the Loop, aided by tasty fixes like steak frites, mango margaritas, and “Summer Love” sangria.
How to book: Reserve via OpenTable.

The Robey Chicago
The Robey Chicago
The Robey Chicago

Cabana Club

Wicker Park
Situated on the sixth floor of the Robey Hotel, this cozy rooftop offers 180-degree views of Wicker Park and the downtown skyline alongside some serious summertime vibes-poolside, no less. Add to the mix an appropriately chill menu, plenty of frosty frose, and dreamy tunes, and you’re entering prime skip-work-on-a-summer-Friday territory.
How to book: Stop by for first come, first served seating.

Reggie’s

South Loop
Proudly calling itself the “Trainwreck Rooftop Deck,” this South Loop rock club’s upstairs expanse offers a delightful diversion from downtown’s chi-chi-leaning al fresco scene. The anything-goes boozy playground features eight flat screens, a pool table, a Pop-A-Shot machine, and picnic tables for snacking on pub grub musts.
How to book: Stop by for first come, first served seating.

LondonHouse Chicago
LondonHouse Chicago
LondonHouse Chicago

LH Rooftop

Loop
Chicago’s only tri-level rooftop extends in glorious fashion from the 21st to 23rd floors of the LondonHouse hotel’s historic Beaux Arts tower. The 23rd floor cupola is only available for private reservations, but nevertheless, it’s hard to find a better spot for mingling with Chicago’s upper crust over lobster biscuits and gravy paired with large format bottles of Armand de Brignac.
How to book: Reserve via Tock.

Homestead
Homestead
Homestead

Homestead on the Roof

West Town
One of the city’s most romantic patios is this 85-seat hideaway, stashed atop Roots Handmade Pizza and engulfed in a lush garden that the kitchen calls upon for much of their menu. The brick fireplace and twinkling lights set the tone for thoughtful cocktails like the gin-laced Secret Garden, a go-to transition for plates like BBQ pork and mushroom ragu fettuccine. Old-school imbibers, you’re covered, too-combos like the bone-in ribeye and Revolution Anti-Hero work just as well.
How to book: Reserve via Resy.

Kennedy Rooftop
Kennedy Rooftop
Kennedy Rooftop

Kennedy Rooftop

Wicker Park
Wicker Park continues to up its rooftop game with the addition of this stunner overlooking the Kennedy Expressway atop the seventh floor of the Hyatt Place Wicker Park. Effortlessly cool, it’s got everything you need for an affable afternoon in the sun, including reliable bites and a stout assemblage of craft cocktails named after American presidents. 
How to book: Stop by for first come, first served seating.

Lonesome Rose
Lonesome Rose
Lonesome Rose

Lonesome Rose

Logan Square
For laidback open-air boozing in one of the city’s hippest ‘hoods, head to this cheerful Land & Sea emporium festooned with Tex-Mex-inspired décor and enough tequila to keep you fully entertained. Bask in the sun while sampling through an extensive array of tacos, burritos, and bowls-all on-point chaperones for a few rounds of palomas and margs. Later, let those hot summer days lead you straight into dessert-horchata and coconut soft serve are calling.
How to book: Reserve via Resy.

Offshore Chicago
Offshore Chicago
Offshore Chicago

Offshore

Streeterville
No rooftop roundup would be complete without inclusion of this 56,000-square-foot destination, which debuted last year as the largest rooftop venue in America. Perched atop the third floor of Navy Pier’s Festival Hall, the spacious hang offers plenty of room for social distancing plus A-grade views of the lake and an aptly-themed bill of coastal bites like crab maki rolls and Faroe Island salmon alongside uplifting sippers like the Sparkling Sapphire (Bombay Sapphire gin, lychee, cucumber, ginger, lemon).
How to book: Reserve via OpenTable.

The J. Parker
The J. Parker
The J. Parker

The J. Parker

Lincoln Park
For stellar, unobstructed views of the lake and Lincoln Park alike, visit this neighborhood favorite, found within the Hotel Lincoln. With a retractable roof and an excellent burger (not to mention truffle fries and crispy brussels sprouts), this perennially-cool option-named after one of Lincoln’s bodyguards, no less-holds court as a pillar of Chicago’s year-round drinking scene.
How to book: Stop by for first come, first served seating.

Utopian Tailgate
Utopian Tailgate
Utopian Tailgate

Utopian Tailgate

Old Town
This fun-filled 10,000-square-foot playpen atop legendary Second City opened to much fanfare last summer, and remains one of the city’s most popular outdoor options. Ablaze in vibrant colors and packed with group-friendly games like giant Connect Four and cornhole, it radiates with the same kind of joy that fuels the rest of the landmark building where some of the world’s most lauded comedians got their start. Swing by for some tailgate-themed food and tropical bevvies while relaxin’ in style via neon-hued Adirondack chairs.
How to book: Reserve via Resy.

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Nicole Schnitzler is a contributor for Thrillist. 

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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