Why raise the roof when you can drink on it?
Chicago’s temperatures are only outdoor-drinking-friendly for a few glorious months and we take full advantage of every moment. Patios are plentiful, but when was the last time you elevated your drinking and dining game with an incredible rooftop view? Talk the elevator to the top to hang out at these bars and kick back with a Jack Daniel's cocktail.
Photo via Virgin Hotels Chicago
Virgin Hotels’ Cerise rooftop bar strikes gold with its winning combo: quirky interior, beautiful downtown views, top-notch music programming and drinks that aren’t stupid expensive. It’s one of your best options if you’re looking to go the hotel bar route.
Photo via IMR Chicago
The Robey 2018 W. North Ave. - Wicker Park
The Robey’s Cabana Club ups the rooftop game in Wicker Park. Find a lounge chair, let the cool breeze hit you, drink a Paloma and listen to the Blue Line whiz past below.
Twisted Spoke 501 N. Ogden Ave. - River West
Drinking one of Twisted Spoke’s six house-recipe Bloody Marys atop its second-story rooftop garden is one of our favorite summertime hangover cures. Don’t take our word for it though. Try it for yourself!
Fountainhead 1970 W. Montrose Ave. - Ravenswood
You’ll find a bevy of beer geeks hanging out on Fountainhead’s rooftop during summer months. Find your next favorite local brewer. Try the food because it’s great. In other words, make a whole night of your time at this North Side gem.
Photo via Heron Agency
Standing at the corner of State and Lake? Can’t find the source of the crazy party you keep overhearing? Look up. ROOF On theWit rages hard. You’ll regularly catch the best local and touring DJs keeping the dancefloor moving at this rooftop hotel club.
Photo: Eric Kleinberg
The J. Parker 1816 N. Clark St. - Lincoln Park
Regularly recognized as one of the best views in the city, The J. Parker (on top of Hotel Lincoln) is what your Instagram feed has been missing.
Rock Bottom is a classic happy hour spot for Chicagoans with downtown offices. Its rooftop gets extra rowdy in the warm months.
Photo courtesy of Drumbar
Drumbar 201 E. Delaware Pl. - Streeterville
Everything about Drumbar (part of the Raffaello Hotel) is lavish—its cozy leather couches, the outdoor garden, the intricate cocktails, the vast whiskey selection. If you can’t find something that you love about this rooftop bar, we suggest looking a little harder.
Photo via IMR Chicago
Homestead 1924 W. Chicago Ave. - West Town
Homestead is a farm-to-table-loving foodie’s paradise. The rooftop West Town restaurant focused on New American fare and many of the ingredients are plucked right from the surrounding garden.
Estate Ultrabar 1177 N. Elston Ave. - Noble Square
Wave to the pontoons as they drift by while chilling on this upriver bar’s rooftop.
Photo via ZED451
ZED451 739 N. Clark St.
If you thought ZED451’s upscale Brazilian steakhouse-style dining experience was the only reason to visit, you’ve obviously never seen the entire place. Its sunny, couch-filled rooftop is the perfect place for happy hour or Sunday mimosas.
Reggies 2015 S. State St. - South Loop
There’s nothing better than a rock show and rooftop hangs. That’s exactly what Reggies in South Loop has to offer seven nights a week.
Bottom Lounge 1375 W. Lake St. - West Loop
If you love an off-the-beaten-path hangout and good views of Willis Tower (forever “Sears” in our hearts”), Bottom Lounge’s rooftop should prove a pleasant surprise. Stop by for pre-show drinks the next time you have tickets to the bar’s venue portion. Just make sure the patio is open first.
Plymouth is one of the few spots on this list offering a rooftop that’s open all year round. The South Loop staple stays warm in the winter thanks to enclosures and heaters. You can’t beat the $4 daily kitchen specials either.
Photo via IMR Chicago
Apogee Lounge 2 W. Erie St. - River North
Apogee Lounge is the perfect place for cocktail drinkers with a sense of adventure and imagination. Have fun sipping a beverage that looks it came from the world of Alice & Wonderland while sitting 26 floors up.
Fig & Olive 104 E. Oak St. - Streeterville
Fig & Olive is a Mediterranean culinary treat in the center of Gold Coast with a beautiful outdoor dining space.
Cindy's 12 S. Michigan Ave. - The Loop
Cindy’s, the centerpiece of Chicago Athletic Association Hotel, offers one of the best views of Millennium Park. More of a restaurant than a bar, it’s best to make reservations in advance at this popular rooftop. Head to the hotel’s Gameroom for a round of drinks and Bacci ball after dinner.
The food at Bernie’s Lunch & Supper gets a lot of praise, but it’s the rooftop that’s the real star of the show during the summer.
Londonhouse 85 E. Wacker Dr. - The Loop
It doesn’t get any more central than Londonhouse’s 22nd-story outdoor terrace overlooking the Chicago River, Michigan Avenue and—basically—the heart of the city.
Mahalo 1501 N. Milwaukee Ave. - Wicker Park
Ramen on the rooftop? Hell yes. Mahalo’s tropical rooftop deck will have you hoping summer never ends.
Photo via Heron Agency
Raised 1 W. Upper Wacker Dr. - The Loop
If you’re really looking to impress out-of-town friends, Raised will be perfect proof of why Chicago does it better. Nestled at the bustling corner of State and Wacker, everything here is done to the nines—from the drinks to the decor to the decadent frites.
Joy District’s roof offers a funky, urban feel along River North’s stretch of Hubbard St. The prime location means it’s a solid spot for daytime or after dark drinking.
Photo via Agency 360
Aurelio's Pizza 1212 S. Michigan Ave. - South Loop
Pizza doesn’t always need to be served on the ground level. Aurelio’s South Loop location is your best destination for a rooftop pie.
Parlour Pizza 108 N. Green St. - West Loop
Both Parlour Pizza locations have excellent outdoor dining (and ping pong!) areas, but only the original West Loop bar and restaurant offers rooftop views. Go for brunch and experience one of the best Bloody Mary bars in the neighborhood.
Satisfy rooftop cravings in any weather at The Godfrey Hotel's gorgeous indoor/outdoor fourth-floor rooftop bar.
WhirlyBall 1825 W. Webster Ave. - Bucktown
When WhirlyBall upgraded to its new space in Bucktown, it also gained a second-floor outdoor terrace complete with several communal fireplaces. Cool down (or warm up) after a game of WhirlyBall (a combination of bumper cars, lacrosse and basketball for those not in the know) or bowling or LaserTag.
Photo: Anthony Tahlier
Devereaux 1112 N. State St. - Gold Coast
Devereaux, part of the new Viceroy Chicago hotel, is new to the game this summer. The swanky new space feels more like Hollywood in the '70s than present-day Chicago. Oh, and did we mention there's a pool?