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The 1 Thing You Must do this Week: From the Bottom to the Rooftop

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Best Rooftop Bars in Chicago

This is an updated version of a post originally published in the summer of 2014.

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. Clothing stores are shoving their best duds out onto the sidewalks. And we’re all eating al fresco whenever possible.

Spring has arrived — foreals this time.

The weatherman’s horoscope, aka the Farmers’ Almanac, predicts this summer will be “hotter and slightly drier than normal”— perfect for happy hours en plein air. Fortunately, Chicago is experiencing a bit of a rooftop boom, driven largely by hotels eager to cash in on the city’s enviable skyline and warm weather obsession.

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

The Best Rooftops in Chicago

best rooftops in chicago

Grilled Corn Lollipop from Raised

Raised at Renaissance Hotel

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

Why I love it: 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.

  • Recommendations:
    • Eat: Grilled Corn Lollipops
    • Eat: Beef Tenderloin Sliders
    • Eat: Peanut Butter & Jelly Push Pop
    • Drink: Spanish Proposal
    • Drink: Vieux CarrĂ©bean

The J. Parker at Hotel Lincoln

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

Why I love it: Far away from the Tinder dates of downtown rooftops, The J. Parker caters more to friends and colleagues winding down after 5 p.m. The panoramic view of Lincoln Park and Lake Michigan is impressive. The skyline looks almost suburban from here. Although the place is always crowded, expect a more friendly atmosphere. Arrive early to secure a table. Enclosed seating available.

  • Recommendations:
    • Eat: Housemade Charcuterie
    • Eat: Cheese Selection
    • Eat: Hand-Cut Fries
    • Drink: Moonage Daydream
Best rooftops in Chicago

“Orange is the New Wacker” from Aire

Aire at Hyatt Centric

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

Why I love it: Aire has the “it” rooftop formula mastered. Three sides of city views. Sharable, portable bites. Strong drinks with cheeky names. Tableside fires, and, coming soon, a large screen television — hopefully, in time for the Euros.

  • Recommendations: 
    • Eat: Midwest Flat Bread
    • Drink: Orange is the New Wacker
    • Drink: More Bang for Your Buck

Fire & Ice #boomerang

A video posted by Kari, Editor of Chicagoings (@chicagoings) on

Vertigo Sky Lounge at Dana Hotel

Vertigo Sky Lounge, 2 W Erie St, Chicago, IL 60654; 312-202-6060

Why I love it: Vertigo Sky Lounge quietly has one of the best rooftop views of Chicago. It’s a great place to hop without the hoopla. Grab a few marshmallows and feel free to toast s’mores on the open fire pit when the temperature drops and the roof is transformed into the city’s only outdoor ice bar. Enclosed seating available.

  • Recommendations:
    • Drink: Shots or Prosecco

cindy's chicago

Cindy’s at the Chicago Athletic Association

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

Why I love it: Last but not (at all!) least, Cindy’s at the Chicago Athletic Association has been Chicago’s most talked about rooftop since its opening last year — 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 night long. Overlooking “the Bean” and Millennium Park, sip on something carefully mixed by the hotel’s serious beverage team. During the weekend, brunch service offered here is one of the best in the city! Most of the rooftop is enclosed under a beautiful glass canopy.

  • Recommendations: 
    • Eat: Pancakes (Brunch)
    • Eat: Cast Iron Quiche (Brunch)
    • Eat: Cast Iron Dutch Apple Pie
    • Drink: Something with Bourbon

Have a few recommendations of your own? Feel free to leave them in the comments section below or on our Instagram, Twitter, Facebook, or find us on Snapchat!

Kari Herrera is the creator of Chicagoings.com, Chicago’s indie city guide and blog. She often writes about the city’s points-of-interest as experienced by a local. She is a Social Media Marketing Manager and freelance writer. When she’s not working, Kari donates much of her time to the education of French-speaking immigrants in Chicago.

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