Fireball Whiskey Apple Pies: A Dessert Fit for a Frat Party
International flare and epicurean eats at buzzworthy newbie
One of the most buzzworthy new openings of 2018 is this internationally inspired stunner on the sixth floor of the Peninsula Chicago off the Mag Mile. So the next time you’re looking to duck tourists shopping for the latest American Girl doll, pop into this globally curated hotspot for epicurean eats like steak fondue, lobster BLTs, and daikon frites paired with craft cocktails and live DJ tuneage. You can also take classes at their monthly Wanderlust spirits series, so go ahead and learn something next time.
A taste of Hollywood located down a Gold Coast alley (with pool!)
With sexy blue lighting reflecting off the pool to illuminate a sultry summertime vibe on the 18th floor of the Viceroy Chicago, this newish spot from Boka Restaurant Group (opened last fall) packs a lot of action into a small, intimate space. With an entrance located down an alley off State Street, this Hollywood-style oasis offers glamorous vistas of the Gold Coast paired with small bites like tuna poke, fried chicken and pickle bites, and boozy Dreamsicle Push Pop ice cream. Sip a Salty Dog or Pipeworks Ninja Vs. Unicorn as you get to know your latest Tinder date with a well-dressed crowd of laid-back revelers.
Uniting the Middle East with unparalleled beauty (and bagels)
Is there room for yet another new rooftop in Chicago? This newly opened beauty from Lettuce Entertainment Group answers strongly in the affirmative. The 4,000-square-foot third-floor rooftop (with private events space) is decked out with posh seating, lush greenery, and firepits that will have you sticking around far longer than you should as you dive into a Mediterranean-inspired menu of falafel, lamb tartare, and Jerusalem bagels paired with “ancient civilization” wines from Greece, Israel, and Lebanon. One thing the entire Middle East can agree on: This place is a winner.
Hipster chic spot for Malort shots, burgers and DJs
Located on the seventh floor of the Ace Hotel, this approximately one-year-old space offers all the hipster-approved credentials you might expect from the famously cool hotel such as Malort shots, Off Color beer on draft, and plenty of Instagrammable mezcal cocktails. Yet despite taking its name from a John Prine song, the Midwestern-style watering hole is friendly not standoffish. Stop by on Mondays for a $6 beer & a shot, burger, and classic cocktail, or any day of the week for addictive bar snacks like short rib nachos and hash browns soundtracked by live DJs.
Your Japanese exchange student is now a rooftop
Meaning “hidden roof” in Japanese, this picturesque 21st floor space atop the Conrad Hotel is like a Japanese exchange student who came to Chicago and never left. And you’re glad as hell for it. Opened in May 2017, this space is like a cultural exchange program off the Mag Mile where rooftop sushi, California roll nachos, and duck bahn mi lunch boxes offer an inventive alternative to traditional Chicago rooftop fare. Sip a Japanese beer, sake, highball, or Japanese whiskey-packed Lost In Translation cocktail before closing your globetrotting experience with a boozy snowball spiked with chocolate vodka.
Classy scene with neighborhood vibes at Lincoln Park mainstay
If you're sick of the same old Downtown rooftop scene, this happening spot 13 floors above the Hotel Lincoln offers a welcome respite as well as massive lake views unobstructed by Lincoln Park if you'd rather look at trees than buildings. With a retractable roof and an excellent burger, this always-cool option named after one of Lincoln's bodyguards remains a Chicago summer essential.
Overlook Millennium Park with a drink in hand atop the CAA
It's the best bar in the Loop, not to mention one of the city's most beautiful. So yeah, by now you know all about the stunning top-floor oasis atop the Chicago Athletic Association and its most Insta-worthy view overlooking Millennium Park. But that doesn't make you want to go there any less, now does it?
Friendly vibes and a deep booze menu in Ravenswood
More restaurant than bar, Fountainhead makes the list by virtue of one of the most pleasant rooftops in the city. Yeah, we said pleasant. Got a problem with that? Well, let's sort it out over a few of the 150-plus whiskies or 27 beers on tap with another 118 in bottles. Also pleasant? Your buzz.
One of the all-time greats serves some of the best drinks in the city
Are you tired of reading articles about the best Chicago rooftop bars and always seeing Drumbar? Well too bad, because the near-unanimous accolades exist for a reason. Several, actually. Like some of the finest cocktails in the city, a sexy 18th floor vibe above the Raffaello Hotel, and a ridic outdoor lounge with primo views of the lake and downtown. Grab a seat and stay a while or, what the hell, grab a room and keep the party going.
An unpretentious alternative to the downtown rooftop scene
Refreshingly less chic than your typical downtown rooftop, this affable and unpretentious space of family-style seating, turquoise banquets, and coffered ceilings is a casual hangout for ordering up the house-ground Bernie's cheeseburger paired with bourbon drinks, Hemingway daiquiris, and margaritas.
Raise the roof at this peaceful downtown stunner
Is it possible to attend a place called Raised An Urban Rooftop Bar without putting your arms in the air to declare your intent to “raise the roof?” If you're not a total creep, it's actually pretty easy. It's also easy to love this stunner on the third floor of the Renaissance Chicago that turned a formerly unused meeting space into a gleaming indoor/outdoor rooftop deck with urban gardens, punch bowls, and sexy VIP areas for sipping in seclusion.
Breezy vibes and PBR tallboys bring a taste of LA to the Loop
Somehow slipping under the radar on the 26th floor of the Virgin Hotel, Cerise’s posh flagship terrace wraps around three sides of the building. With offbeat art and DJs spinning under twinkling lights inside, this casual chic space brings a slice of LA to the Loop, aided by shrimp skewers, bourbon mules, and PBR tallboys. Do it.
Eat and drink on communal tables above a neighborhood sausage shop
If you don't love the delightful rooftop patio above this equally delightful Lincoln Square sausage shop, you might not be human (or at least not from Chicago). With communal wooden tables and an abundance of greenery, this relaxing European-style spot is the perfect place to tackle plates of goulash and 40+ types of smoked sausage while seeing how many beers and wines you can ingest on a Sunday afternoon before dialing into work “sick.”
Party South Beach-style at this iconic downtown rooftop
No lineup of rooftop bars in Chicago is complete without the inclusion of ROOF on theWit. It's as essential to the Chicago rooftop scene as a White Castle slider atop your Bloody Mary. In other words, not very. But still nice to have as well as having live DJs, runway shows, and a retractable roof.
Instagram likes are guaranteed 26 floors above the city
Replacing the old Vertigo Sky Lounge space atop the 26th floor of the Dana Hotel is this opulent mainstay, featuring stunning, innovative cocktails from local mixology kingpin Benjamin Schiller. The insanely Instagrammable inventions include drinks served in glass bongs and cocktails with unique touches like light lightning bolts and edible paper butterflies. The beautiful 1,100-square-foot space also has a comfortable lawn section and firepits for the colder evenings.
A Wicker Park two-for-one with a cool crowd and pool
The Up Room and the Cabana Club are two rooftop bars in one building, thanks to the Robey’s collaboration with its sister property, The Hollander. The Up Room is the hotel’s older 13th-floor lounge, offering expansive views of the city and Robey spire (just resist the urge to scale it after ingesting a Holy Cow! cocktail, which combines Hennessy Black with salted caramelized milk, coffee, and tobacco bitters). Opened in May 2017, the sixth-floor Cabana Club has a shimmering pool and a 160-seat outdoor deck where you can enjoy Latin bites and Mexican-inspired drinks.
A boozy Zen oasis hidden in the middle of the city
This third-floor oasis at the Loews Chicago is here to relax you. The large terrace is like a Zen zone in the midst of the bustling city, with large grassy areas, giant Jenga, cozy swing chairs, and great views of the lake. Grab a spot in the afternoon and enjoy some tiki cocktails as you watch the sunset. They’re so delicious, you’ll probably end up staying much later.
Standout bar eats and games above a South Loop punk venue
Proudly calling itself the “Trainwreck Rooftop Deck,” the South Loop rock club’s upstairs area offers a delightful diversion from the stuffy Downtown outdoor scene. The anything-goes 99-person playground features eight flat screens, a pool table, a Pop-A-Shot machine, cornhole, and picnic tables for munching on the standout bar menu offerings. Stop by before a show to get appropriately loose and boozy.
Retractable roof with dance floor and lamb lollichops
The 15,000 square foot venue on the fourth floor of the Godfrey Hotel has a retractable roof, a video wall, a fire pit, and a well-dressed crowd. Down a lamb lollichop and Lagunitas, then bust a move under the massive dance floor’s trippy lights.
Mingle with the upper crust and this aristocratic playpen
Chicago’s only tri-level rooftop extends in glorious fashion from the 21st to 23rd floors above the London House hotel, located in a 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 picnic baskets packed with venison sausage, trout rillette, and various snacks. You can even stop by for afternoon tea service if you’re feeling particularly aristocratic.
Get down and dirty atop Chicago’s favorite biker bar
From its famous “Smut & Eggs” late-night porn viewing sessions to its standout whiskey and Bloody Mary collections, not to mention some of the best nachos and jalapeño poppers in the city, Twisted Spoke has a lot going for it. It seems almost unfair that everyone’s favorite biker bar also happens to have one of the finest rooftops in the city, an oasis of day drinking where you can get into just the right amount of trouble.