It’s unofficially summer in Chicago, at least to us. Rooftops have already reopened, and drinks will soon be served frozen, or if you’re Upstairs at The Gwen, it’ll be in the form of a popsicle (hello, DIY margarita pops). Without wasting any time, we’ve mapped out the city’s best rooftop bars. Not only do these spots have delicious drinks—or, in the case of Cindy’s Rooftop, elixirs and potions—but some are also designed how we wish our apartments would look.
To jump ahead, look at the simplicity of the J. Parker, and The Robey and the herringbone floors and gold accents at the Kimpton Gray Hotel. Gorgeous, right? But we’re going off on a tangent—keep scrolling to see our eight favorite places to enjoy crafty cocktails and the best views of Chicago. No reservations required.
Located in the financial district, this retractable rooftop restaurant and bar serves Peruvian and Argentinean small plates, has happy hour on Wednesday and Thursday evenings from 5 to 8 p.m., and hosts deejays on various nights of the week (check out the schedule). PS: It’s situated on the 15th floor of the new Kimpton Gray Hotel, and the décor is everything.
Boleo: 122 West Monroe Street, Chicago
Up & Up
On the 13th floor of The Robey is Up & Up, the industrial, minimally designed indoor/outdoor lounge. Oh, and if you’re looking for a pool-side spot this summer, Cabana Club, on the 6th-floor terrace, has a bar, restaurant, and patio all open to everyone, not just hotel guests. Swimming rights come only to those who show a room key.
The Robey: 2018 West North Avenue, Chicago
The J. Parker
The J. Parker, above Hotel Lincoln, is giving us major design inspiration. Stunning décor aside, try one of the signature cocktails inspired by different parts of the world, like Vino de Sol, which takes cues from Spain and is made with Ketel One Vodka, white wine, pear liqueur, passion fruit, honeydew, triple sec, and lemon.
J. Parker: 1816 North Clark Street, Chicago
Upstairs at the Gwen
As the name suggests, this outdoor bar is on the fifth floor of the newly renovated Gwen hotel. Though all you really need to know is that it serves frozen prosecco popsicles.
Gwen: 521 North Rush Street, Chicago
Rooftop at LondonHouse Chicago
Perched on top of the LondonHouse Chicago is this three-level rooftop lounge. Sip jazz age–inspired cocktails at the indoor bar on the 21st floor or opt for drinks on the outdoor terrace of the 22nd floor. At the highest level is a private copula.
LondonHouse Chicago: 85 East Upper Wacker Drive, Chicago
The wine selection at Cindy’s Rooftop—which is also one of our favorite restaurants in Chicago—focuses on women vintners, sustainable practices, and resurrected varietals. Amazing, right? The restaurant and bar’s dinner drink menu is also five pages and includes elixirs and potions.
Cindy's Rooftop: 12 Michigan Avenue, Chicago
GreenRiver is a Michelin-starred restaurant and bar, has one of Chicago’s largest outdoor terraces, and is on the 18th floor, with views of Lake Michigan and the city’s skyline. We’re getting in line because outdoor seating is on a first-come, first-served basis.
GreenRiver: 259 East Erie Street, 18th Floor, Chicago
Bernie's Lunch & Supper
This summer, Bernie’s will be serving frozen cocktails from margaritas to pisco sours on its second-story rooftop bar. Also, enjoy the full dining menu that’s served on the first floor.
Bernie’s: 660 North Orleans Street, Chicago
Shae your favorite rooftop spots and lookout points to catch the views in Chicago in the comment section below.