Food & Drink

The Best Rooftop Bars in Chicago

Get a little fresh air (and a lot of booze).

With street festivals on hiatus, Wrigley Field shuttered to fans, and beaches still off limits, there is one classic Chicago summer activity that Covid can’t take away from us: the sheer unadulterated joy of drinking on a rooftop. While many of Chicago’s classic rooftop hangs remain temporarily closed due to the virus, a good number of newbies have popped up in recent years to help keep the vibe lively and diverse. So whether you’re looking to impress with fancy Champagne and caviar overlooking the downtown skyline or just want to kick back in your neighborhood with a burger and some cheap beer, we’ve got you covered with our roundup of the best rooftop bars in Chicago.

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.

Aba

Fulton Market
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.

The J. Parker

Lincoln Park
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 hush puppies), this always-cool option named after one of Lincoln's bodyguards remains a Chicago summer essential.

Fountainhead

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 plus 40 canned beers and ciders.

Cerise

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 a new pop-up dine and drink experience starting at noon daily, this casual chic space brings a slice of LA to the Loop, aided by kobe steak, mango margaritas, and PBR tallboys.

Robey Chicago
Cabana Club at the Robey | Adrian Gaut

The Up Room

Wicker Park
The 13th-floor lounge at the Robey offers expansive views of the city in an area not traditionally known for panoramic rooftop vistas. The Up Room lends itself to date night, so head to its wraparound terrace and take in the shimmering skyline. 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.

Cabana Club

Wicker Park
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. 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.

Streeterville Social

Streeterville
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, 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.

Reggie’s

South Loop
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 to get appropriately loose and boozy.

I|O Godfrey

River North
This 15,000-square-foot indoor/outdoor rooftop 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 with a good-looking, well-dressed crowd. Seating is currently limited to one hour and 15 minutes for dining services, and they also offer an “IO2GO” menu for those not yet comfortable mingling with other humans.

LH Rooftop

Loop
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 lobster biscuits and gravy paired with $1,800 bottles of champagne. Hey, at least you can pretend.

Boleo

Loop
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 pollo 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. Orders are also available for pickup.

Homestead on the Roof

West Town
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 rum-packed Velour Tracksuit paired with brisket tacos and Mexican street corn. But if you want to keep it classic, there’s nothing wrong with the NY strip steak and a can of Revolution Anti-Hero.

VU

South Loop
South Loop residents remain pumped about this 13,000-square-foot space rising 22 floors above the city, next to McCormick Place. The food menu features dishes like fried chicken sandwiches and mushroom Sloppy Joe’s -- or lobster chilaquiles and jerk chicken & waffles for brunch -- but feel free to just post up with a drink and enjoy the skyline views for a while.

Bottom Lounge

West Loop
While this iconic punk rock venue and longtime Chicago institution remains closed for music for the time being, its stellar rooftop patio remains open for business -- offering some of the best views in the area with a cool crowd in a laid-back setting. Instead of pricey champagnes and steaks like many of the Downtown haunts, this neighborhood-centric hidden gem offers a more affordable rooftop excursion with $3 PBR cans and no-fuss bar eats like burgers and grilled cheese.

Offshore

Streeterville
No roundup of local rooftops would be complete without inclusion of this gigantic 36,000-square-foot rooftop at Navy Pier, which opened last year as the largest rooftop venue in America. Perched on the third floor of Navy Pier’s Festival Hall, the spacious hang offers plenty of room for social distance plus A-plus views of the lake to pair with coastally-inspired bites like crab maki rolls and Faroe Island salmon. Yeah, it’s $17 for a burger. But as they say, you’re paying for the view.

Utopian Tailgate

Old Town
This fun-filled 10,000-square-foot playpen atop the legendary Second City opened to much fanfare last summer, and remains one of the city’s most popular rooftop hangs even in the age of covid. Ablaze in an orgy of vibrant colors and packed with group-friendly games like giant Connect Four and cornhole, it’s not hard to see why. So stop by for some tailgate-themed food and tiki drinks while kicking back in a brightly colored Adirondack chair. You deserve it.

Kennedy

Wicker Park
Wicker Park ups its recently expanding rooftop game even further with the addition of this fun rooftop space overlooking the Kennedy Expressway atop the seventh floor of the new Hyatt Place Wicker Park. Cool without trying too hard, it’s got everything you need for an affable afternoon in the sun including solid bar eats and a stout assemblage of craft cocktails named after US presidents. 

Joy District

River North
With leafy ivy set against brick walls plus colorful murals and twinkling lights rounding out the Insta-worthy experience, Joy District has long been one of Chicago’s most popular downtown rooftop hangs. Grab pizza, tacos, and burgers paired with frozen cocktails and 33-ounce “punch pouches” as you chat up friends in the typically lively (yet rarely annoyingly-so) space. And that’s really all you want in a rooftop, right?

Lonesome Rose

Logan Square
Given how densely packed the neighborhood is with buzzworthy bars and restaurants, the relative dearth of rooftop hangs in Logan Square comes as a bit of a head-scratcher. Laid-back neighborhood spot Lonesome Rose seeks to rectify that situation with a cozy rooftop space that may not offer the best views in the city, but gets the job done for those looking for some rooftop vibes in the hood. The Tex-Mex-inspired space serves up staples like tacos and burritos paired with pitchers of margaritas, Lone Star beer, and Mexican Coke.

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Jay Gentile is a Thrillist contributor and professional rooftop drinker, or so he likes to think. Follow @innerviewmag.