Charleston: The Ultimate Local's Guide
International flare and global flavors on a buzzworthy rooftop
One of the most buzzworthy new 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 steak fondue, Malaysian chicken and beef satay, and daikon frites paired with craft cocktails and a live DJ. 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 a pool!)
With sexy blue lighting reflecting off the pool to illuminate a sultry summertime vibe on the 18th floor of the Viceroy Chicago, this sleek stunner from Boka Restaurant Group 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 the likes of fried chicken and pickle bites. Sip a Salty Dog or Haymarket Speakerswagon Pilsner as you get to know your latest Tinder date with a well-dressed crowd of laid-back revelers.
Mediteranian cuisine and lush greenery (and bagels)
This 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 short rib hummus, lamb ragu, and Jerusalem bagels paired with “ancient civilization” wines from Greece, Israel, and Lebanon.
Hipster chic spot for burgers and avocado toast
Located on the seventh floor of the Ace Hotel, this two-year-old space offers all the hipster credentials you might expect from the famously cool hotel chain -- like, Stumptown coffee and the popular City Mouse restaurant project in collaboration with Giant. Stop by on Mondays for a $6 beer & a shot, burger, or classic cocktail.
Classy scene with neighborhood vibes at a 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 huge lake views unobstructed by Lincoln Park if you'd rather look at trees than buildings. With a retractable roof and an excellent burger (not to mention truffle fries and pork nachos), 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 stacked selection of whiskeys or 12 rooftop beers on tap with another 62 in cans. 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.
Breezy vibes and PBR tallboys bring a taste of LA to the Loop
Keeping things cool 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 octopus ceviche, mezcal margaritas, and PBR tallboys. Do it.
Instagram likes are guaranteed 26 floors above the city
This opulent outpost atop the 26th floor of the Dana Hotel is best known for its stunning, innovative cocktails tailor made for Instagramming. The insanely inventive 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 boozy Wicker Park stunner with the best view for miles
The 13th-floor lounge at the Robey offers expansive views of the city in an area not traditionally known for panoramic rooftop vistas. The dark, stylish interior has a brooding Mad Men feel and is open year-round, but space is limited, so head to the wraparound terrace to take in the shimmering skyline. The Up Room lends itself to date night -- a secluded alcove within the bell tower is particularly cozy if the weather’s less than perfect -- but ambiance and scenic views aside, the cocktails are phenomenal. Oaxacan on Broken Glass is a spicy-yet-refreshing mezcal concoction that is, most importantly, very fun to say.
Hang poolside with frozen cocktails and sweeping vistas
But wait! There’s more! The Robey hotel boasts a secondary rooftop, open seasonally on its sixth floor. Three hundred sixty-degree views of Wicker Park and the Downtown skyline? Check. Great bar? Check check (there are two!). A little less scene-y than its Up Room sibling, Cabana Club serves up frozen cocktails and laidback summertime vibes poolside. OK, it’s more like a kiddie wading pool, but that doesn’t discourage the clientele from stripping down to their suits. A bar menu and decent tunes make this a primo skip-work-on-a-summer-Friday spot.
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.
CBD cocktails and a retractable roof with a dance floor
This 15,000-square-foot venue on the fourth floor of the Godfrey Hotel has a retractable roof, a video wall, a fire pit, and now… CBD cocktails? Yes, you can now add cannabidiol to your cocktail or play it straight by downing a lamb lollichop and an I|O Cosmo before busting a move under the massive dance floor’s trippy lights.
Mingle with the upper crust at 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 20-layer lasagna and roasted duck breast. You can even stop by for afternoon tea service if you’re feeling particularly aristocratic.
Peruvian street food and Argentine cocktails 15 floors up
This sexy South American hotspot on the 15th floor of the Kimpton Gray Hotel keeps it classy with a massive year-round retractable glass rooftop and a menu inspired by Peruvian street food like plantain chips and carne empanadas. For booze, there’s classic south-of-the-hemisphere mainstays like the Argentine staple Fernet & cola and some of the finest pisco concoctions you’ll find on any rooftop. Can’t decide? Split a bunch bowl and get weird.
Shuffleboard on a 162-seat rooftop deck
One of last summer’s hottest additions to the city’s growing rooftop scene is the 162-seat rooftop “Lido Deck” at the hipster-approved Royal Palms Shuffleboard Club. Even if you’re not among the skinny-jean set, you’ll find plenty to love at this spacious and sunny hang. Is there a bar? Obviously. Is there a shuffleboard court? Duh. Challenge all comers with drink in hand and find something new to brag about this summer.
Romantic patio with a fireplace and garden
One of the city’s most romantic patios is this adorable little 85-seat rooftop oasis decked out in full garden style above popular West Town pizza joint Roots Handmade Pizza. The brick fireplace and twinkling lights set the mood for cocktails like the Homestead Lunchbox (vodka, ginger liqueur, and lime with an IPA float) paired with intriguing plates like pork rillette ramen and bánh mí toast. But if you want to play it safe, there’s nothing wrong with the hangar steak frites and a can of Revolution Anti-Hero.
Three bars and two patios in an expansive space near McCormick Place
South Loop residents are getting pumped for the first summer season after the penthouse-style VU rooftop opened last fall. The 13,000-square-foot space is 22 floors above the city, next to McCormick Place. The food menu features a wide range of dishes, like Peking duck tacos and Nashville hot chicken sandwiches -- or lobster chilaquiles and chicken & waffles for brunch -- but feel free to just post up with a drink and enjoy the skyline views for a while.
Old Faithful for classic Chicago rooftop vibes and peach sangria
While technically a Brazilian steakhouse, ZED451 can always be relied on for an all-around solid Chicago rooftop experience, with everything you need in the form of drink specials, a sociable crowd, and killer Downtown views. Also, the peach sangria is what summer is all about.