Summertime Drinks at Chicago’s Rooftop Bars

Despite its jaw-dropper skyline and balmy summer climes, rooftop bars are surprisingly far and few between in Chicago. We’ve tirelessly snooped, sipped and traipsed up stairs to bring you the very best of Chicago’s breezy rooftop bars.

With Lake Michigan framed by Lincoln Park treetops to your left and wham-bam Downtown skyline to your right, 13th-floor The J Parker wins on spectacular city views alone. And the recent addition of a conservatory-like glass roof means that you can enjoy their spiffy list of seasonal libations and small plates whatever the weather.

Mobbed for its sceney weekend brunch, which includes scrumptious buttermilk-fried chicken and lobster chilaquiles, chef Nolan Narut’s gourmet hideaway VU Rooftop Bar teeters 22 stories above South Loop. A retractable solarium shelters indoor diners, while an ace outside deck is lined with fire pits and TVs for those passing Bears fans.

Perfect for an aperitivo before heading out, or book well ahead for a taste of ‘Chicago’s best Chinese restaurant’ (Zagat), The Peninsula’s Shanghai Terrace graduates from late-afternoon cocktail-slinger to slinky rouge-hued restaurant come 5pm. Either way you sway, you’ll be treated to seamless service, sublime Cantonese delicacies, and seasonal cocktails with glittery city views.

Newbie on the alfresco scene is deli institution Gene's Sausage Shop, who recently extended upwards with the opening of its own rooftop beer garden. Sip ice-cold brews, from German staples Krombacher, Hofbräu, and Tripel Karmeliet to the homegrown Maplewood, on this Oktoberfest-inspired deck with chalet-bar and communal wooden bench seating. It being above a speciality meat shop, beer’s best friend bratwurst makes a regular appearance too.

Primarily a dining destination, with chef Keith Potter plating up locally-sourced sustainable ingredients, Cindy's is cocooned by a vaulted Victorian-style glass-and-steel roof which makes it an all-weather favourite. However, the simple, standing-room-only terrace, with an unobstructed outlook over Millennium Park and Lake Michigan beyond, is where we’ll be found sampling one of the city’s best cocktail programs. Cin cin!

The J Parker / 13/F / 1816 N Clark St / Lincoln Park / +1 312 254 4747 / 11am-11pm Mon-Thurs, 11am-12am Fri, 10am-12am Sat, 10am-10pm Sun / jparkerchicago.com

Vu / 133 E Cermak Rd / Wicker Park / +1 312 256 2990 / 4pm-11pm Sun-Thurs, 4pm-1am Fri-Sat / vurooftop.com

Shanghai Terrace / 4/F / The Peninsula / +1 312 573 6744 / 11.30am-2:30pm Fri-Sun lunch, 5pm-10pm Sun, Wed, Thurs, 5pm-11pm Fri-Sat / peninsula.com 

Gene’s Sausage Shop & Delicatessen / 4750 N Lincoln Ave / Lincoln Square / +1 773  728 7243 / 9am-8pm Mon-Sat, 9am-4pm Sun / genessausage.com

Cindy’s / 12 S Michigan Ave / The Loop /  +1 312 792 3502 / 11am-11pm Mon-Thurs, 11am-12am Fri, 10am - 12am Sat, 10am - 11pm Sun / cindysrooftop.com