Scan this QR Code to follow PureWow on Snapchat!
PureWow

You know the drill. The leaves are turning, your sweaters have reported for duty, and soon hibernation season will be here, too. That means it’s time to be outside as much as possible—preferably while sipping a cocktail and taking in a killer skyline view. We found 20 rooftop bars in Chicago for doing just that.

Editor’s note: In light of COVID-19, please review federal, state and local traveler guidance. Please also check with restaurants and bars before visiting to confirm they are open and operating with safety precautions.

RELATED: The 10 Best Chicago Walking Tours (Most of Which Are Totally Free)

chicago rooftops fountainhead facebook

1. FOUNTAINHEAD

Take your craft beer-fanatic friends to this Ravenswood hangout for an exhaustive list of bottles and drafts. For a high-low approach, pair a refreshing bottle of sparkling rosé with a meat pie for lunch. And make sure to visit ASAP: Fountainhead recently announced that it’s closing until further notice on November 14.

1970 W. Montrose Ave.; 773-697-8204 or fountainheadchicago.com

Celeste Feb2017 1529 HDR
Kohl Murdock

2. CELESTE

The Victorian-inspired spot is one of the few on our list that’s climate controlled; keep it in mind for that late-October chill. A rotating roster of DJs spins beats on the weekends, although the bar’s COVID-era guidelines ask that you “show off your dance moves from the seated position.”

111 W. Hubbard St.; 312-828-9000 or celestechicago.com

chicago rooftops j. parker

3. J. PARKER AT HOTEL LINCOLN

Rain or shine, a retractable roof keeps this spot going strong. From the top, you’ll see Lincoln Park and its zoo, the lake, The Loop and, heck, probably your house.

1816 N. Clark St.; 312-254-4747 or jparkerchicago.com

chicago rooftops chop shop

4. CHOP SHOP

Wednesdays, you’ll find us at this tucked away Wicker Park roof deck for dollar oysters. The deal ends at 7 p.m., so—as they say—chop-chop.

2033 W. North Ave.; 773-537-4440 or chopshopchi.com

chicago rooftops bernies

5. BERNIE’S LUNCH AND SUPPER

We don’t know who Bernie is, but we love his Mediterranean-inspired menu, especially those falafel crispies with dill yogurt. Oh, and the timber-lined rooftop isn’t so bad, either.

660 N. Orleans St.; 312-624-9892 or bernieslunchandsupper.com

RELATED: How to Do Chicago’s Best 5 Tourist Attractions Better Than the Tourists

taxim rooftop bar chicago
Taxim/Facebook

6. TAXIM

Taxim’s roof (known as Hayati) is the next best thing to that trip to Greece you keep dreaming about. Aside from the food (fried cauliflower with whipped goat feta? Yes, please), the candlelight and greenery will have you feeling all kinds of vacation vibes.

1558 N. Milwaukee Ave.; 773-252-1558 or taximchicago.com

Raised rooftop bar chicago
Raised

7. Raised

Imagine: a lobster roll, a mojito, and perfect views of the Marina Towers. What’s not to love? Before you book it to Raised, though, you should probably make a reservation (headcount is currently restricted to allow for social distancing).

1 West Upper Wacker Dr.; 312-795-3444 or raisedbarchicago.com

vu rooftop bar chicago
Vu

8. Vu Rooftop

There’s plenty of room to safely spread out at Vu Rooftop, a 13,000-square-foot bar that boasts 22nd-floor views. Treat yourself to an apple-tini and a pork belly bao while gazing at the lake, the Museum Campus, or at the flickering flames of the fire pit in front of you.

133 E Cermak Rd.; 312-528-0191 or vurooftop.com

9. The Gwen Terrace

The minimalist decor at The Gwen Terrace lets its colorful cocktails take center stage, such as hibiscus lemonade and the “Breakfast Old Fashioned” made with earl grey-infused bourbon. Make a meal out of it with a plate of Spanish octopus with paprika aioli, or go straight for the churros instead, which come with a molé-spiced chocolate ganache.

521 N Rush St.; 312-645-1500 or thegwenchicago.com

plymouth rooftop bar chicago
Plymouth/Facebook

10. Plymouth Bar & Grill

You may recognize the Plymouth Bar & Grill’s dazzling neon signage from your last CTA ride around the Loop—which means you’ve definitely seen its roomy rooftop patio, too. Stop by to sip a martini while admiring views of the Harold Washington Library (and of passing CTA riders who would likely prefer to be in your seat).

327 S. Plymouth Ct.; 312-362-1212 or plymouthgrill.com

11. Z BAR

Raise a toast to the resilient Water Tower and the dizzying heights of the Hancock Center from your perch at Z Bar. Perhaps that glass will be filled with artisanal elderflower soda, or with a Manhattan poured over an ice cube that’s flecked with 24-carat gold. Either way, you can’t go wrong pairing your drink with a side of daikon frites.

108 E Superior St.; 312-573-6888 or zbarchicago.com

12. Whiskey Business

This Wicker Park rooftop’s got it all: 3,000 square feet, 100 whiskies, and all the colors of the rainbow. And there’s plenty to keep you entertained, too, like a slew of movie nights under the stars, or the creepy decor of the new pop-up “haunted cabins” to get you in the mood for Halloween.

1367 N Milwaukee Ave.; 773-698-7362 or whiskeybusinesschicago.com

13. Bottom Lounge

The stage at Bottom Lounge may be silent these days, but you can still show this concert venue some love by stopping by for a snack on its rooftop. Dig in to a fried tofu wrap or a giant pretzel (or both!), paired with a refreshing pint from a list of nearly three dozen beers.

1375 W. Lake St.; 312-666-6775 or bottomlounge.com

14. The Kennedy Rooftop

Enjoy a presidentially themed cocktail, like the Reagan’s Orange Blossom, as you admire the city skyline at The Kennedy Rooftop in Wicker Park. This spot also serves up globally inspired meals of empanadas, Creole-seasoned shrimp, pani puri, and more.

1551 W. North Ave.; 773-270-6770 or kennedyrooftop.com

15. Utopian Tailgate

Squint, and you can almost believe you’re enjoying a regular fall hang with your friends at Utopian Tailgate. This spot leans in to the tailgate theme, offering grown-up versions of game-day treats, like nachos topped with slow-roasted pork and tequila flavored with chili and pomegranate. Try timing your visit with the next big game (which you can watch on flatscreen TVs), or with the occasional workout sessions hosted in this colorful space.

1608 N Wells St.; 312-210-7799 or utopiantailgate.com

16. Streeterville Social

Enjoy a Sweater Weather during sweater weather at Streeterville Social. (That’s the name of their new mulled wine cocktail, FYI.) But if you’d rather cling to more summery vibes, choose from cocktails flavored with passion fruit or grapefruit, or just pick a bottle of rosé. If you’re hungry, check the website to see which local restaurants are currently partnered with Streeterville Social for take-out.

455 N Park Dr.; 312-840-6617 or loweshotels.com

17. Reggie’s

Here’s another chance to support a local music venue by drinking on their roof. Order a pint at Reggie’s and daydream about seeing concerts again while you dig into a plate of wings, tacos, and other pub grub.

2105 S. State St.; 312-949-0120 or www.reggieslive.com

18. Lonesome Rose

It’s hard to say no to the Crunchy Beefy Quesorito at Lonesome Rose, especially when you have the chance to eat it while basking in the sun. Add a spicy margarita, or a glass of the Fireside Sangria to warm you up, and you may never want to leave this Logan Square spot.

2101 N. California Ave.; 773-770-3414 or lonesomerose.com

19. Homestead on the Roof

Surprise! There’s a rooftop bar above Roots Pizza in West Town, and it’s a plant lover’s dream. Stop in for a plate of tacos, some Mexican street corn, and an old fashioned made with mezcal and tequila. And hurry: the restaurant closes for the season in late October.

1924 W. Chicago Ave.; 773-332-2354 or homesteadontheroof.com

20. Boleo

Enjoy South American-inspired cuisine in this glass-roofed spot atop the Kimpton Gray Hotel. Order a caipirinha, plus some ceviche and empanadas, and let your mind wander to your next dream vacation spots.

122 W Monroe St.; 312-750-9007 or boleochicago.com

RELATED: The 25 Best Patio Restaurants in Chicago for Outdoor Dining

From Around The Web