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Chicago’s Best Rooftop Bars and Restaurants of 2018

Chicago's Best Rooftop Bars Aire in The Loop
Photo: Courtesy of Aire

No doubt you’ve noticed something different about Chicago lately. Commuters are smiling. Manicures, pedicures, and bare legs are all over Instagram, as are Crayola colored cocktails glowing beneath tanned fingers. And we’re all eating al fresco whenever possible. Spring is finally here!

The roof is where we all want to be for the few warm months allotted to this city. It’s where the sun shines brightest, and the air is hottest. In Chicago, the roof is the only place you’ll see the best skyline in the world, and with winters as brutal as ours, the rooftop season is one not to be missed.

Here are my picks for Chicago’s best rooftops along with a few suggested plates and cocktails from each. Enjoy!

Chicago’s Best Rooftops

Best Happy Hour Scene: Raised at Renaissance Hotel
Best View: J. Parker at Hotel Lincoln
Best Burgers: Aire at Hyatt Centric
Best Events: Roof on theWit
Best Overall: Cindy’s at Chicago Athletic Association

The best Rooftops in Chicago: Raised

Best Happy Hour Scene: Raised at Renaissance Hotel

Raised, 1 W Upper Wacker Drive, Chicago, Illinois 60601; 312-372-7200
Website

Jutting out just below the uppermost point of the Renaissance Hotel, it offers a terrace view uncluttered by exposed vents and rusty fire escapes. Instead of floating above the city, it’s in the middle of it all. Sip a cocktail inside one of the lounge’s chic cabanas as you watch boats glide under the famous bascule drawbridges. Raised is lined with comfy seating, a performance area for live music, multiple bars, and a smart indoor section for rainy days.

I do have to say, without insulting the talents of any current culinary directors, that Chef Daniel Perez who once oversaw the hotel’s main bar, Staycation, and Raised is sorely missed. He was responsible for one of the best brunches I’ve ever had. The current direction of both Raised and Staycation is less food-forward than it once was, in my humble opinion. So, stick to the cocktails or go with something tried and true like burgers and fries.
Recommendations:

  • Eat: Burgers and Frites
  • Drink: Rampart Rambler — a barrel-aged cocktail that will run you about $20, but it’s pretty amazing

Best View: The J. Parker at Hotel Lincoln

The J. Parker, 1816 N Clark St, Chicago, IL 60614; 312-254-4747
Website

The skyline looks almost suburban from here. This is Lincoln Park, away from the offices and skyscrapers of the Loop. The lookout is unobstructed. The panoramic view of the park and Lake Michigan is impressive. Although the place is always crowded, expect a friendlier atmosphere compared to other rooftops in the city. It’s always packed so securing a table is near impossible. No reservations accepted. Arrive early. Limited enclosed seating available.

It doesn’t look as new as it used to, and so has dipped from its place as my #1 recommended rooftop to #3. Still, worth a visit!
Recommendations:

  • Eat: Stick to fries. Eat elsewhere.
  • Drink: Tortuga, their version of a Piña Colada
  • Drink: Froze, ‘cause it’s trendy and delicious
Chicago's Best Rooftop Bars Aire in The Loop
Photo: Courtesy of Aire

Best Burgers: Aire at Hyatt Centric

Aire, 100 W Monroe St, Chicago, IL 60603; 312-236-1234
Website

Aire has the “it” rooftop formula mastered. Three sides of city views. Shareable, easy-to-handle bites. Craft cocktails and tableside fireplaces. What makes them over the top this year is their pop-up grill featuring Kuma’s Corner, available Saturdays from 4p – 9p. Kuma’s is thought by many to be the best burger in the city. They will be serving their Led Zepplin, Darkthrone, WASP, and Pig Destroyer burgers for $10 during the Saturday evening pop-up.

Recommendations:

  • Eat: Any of the burgers Kuma offers
  • Drink: Draft Beer, my cocktail was a little weak last time I visited, to be honest

Best Rooftop Bars in Chicago

Best Events: Roof on theWit

Roof on theWit, 201 N. State Street, Chicago, IL 60601; 312-239-9502
Website

TheWit is like the popular small-town guy that moves to a bigger city and suffers an identity crisis in a school full of equally gorgeous and popular guys. Let me explain. When the rooftop first opened, what feels like decades ago, it was the hot rooftop scene, no competition. Now, with hotels turning any square foot rooftop space into a bar, there are rooftops everywhere — and many of them offer serious bar programs and menus. So, you know, theWit may be feeling some heat. To compensate, they’re providing all-out carnival every weekend in the summer; day parties, night parties, anytime parties. That’s honestly not my scene, but I will say I always enjoy their Movie Mondays. The sound system is incredible, thanks to all the weekend DJ sets, and the cocktails are fantastic. Recently, their plates have been blowing me away also.

Recommendations:

  • Eat: Fried Chicken full plate
  • Eat: Paella
  • Drink: Death by Old Fashioned

cindy's chicago

Chicago's Best Rooftop Cindy's

Best Overall: Cindy’s at the Chicago Athletic Association

Cindy’s, 12 S Michigan Ave, Chicago, IL 60603; 312-792-3502
Website

It was a tough decision, but I’m recommending Cindy’s as the city’s best rooftop this year. Cindy’s at the Chicago Athletic Association has been Chicago’s most talked about rooftop since its opening— and with good reason! Fire pits on the small outdoor walkway provide minimal warmth during the winter, but the view keeps the area packed all year long. Overlooking “the Bean” and Millennium Park, sip on something carefully mixed by the hotel’s dangerous beverage team. During the weekend, brunch service offered here is one of the best! Most of the rooftop is enclosed under a beautiful glass canopy.

Recommendations:

  • Eat: Pancakes (Brunch)
  • Eat: Cast Iron Quiche (Brunch)
  • Drink: Something with Bourbon, the beverage program here is legit

Have a few recommendations of your own? Feel free to leave them in the comments section below!