Imbibe Outside

From swanky rooftop lounges to cozy patios, here’s a look at concierges’ five favorite places to unwind outdoors.


From swanky rooftop lounges to cozy patios, here’s a look at concierges’ five favorite places to unwind outdoors.

Cerise, the rooftop bar and lounge located on the Virgin Hotel’s 26th floor, boasts a whimsical and playful aesthetic of bold hues, expansive views of Chicago’s historic architectural skyline, and an Izakaya-inspired menu of small dishes that pair perfectly with their beer, wine, and cocktails. The lounge expands the entire width of the hotel, including a terrace that wraps around three sides and an assortment of large, plush couches both indoors and out.



A 300-seat patio with 114 selections of local and global beers available at any given time nestled in the shadows of some of Chicago’s most treasured architectural gems? Yes, it exists. Located adjacent to the Tribune Tower on the Magnificent Mile, Howells & Hood is the perfect spot to people watch, linger, and soak up the glorious spring sun. In addition to their expansive beverage program, they also offer up a menu chock-full of clever twists on American cuisine.

The fourth floor Garden at Celeste is a stunner, transporting you into an urban oasis overlooking the lively River North neighborhood below. With its ivy-covered walls and Victorian-style seating arrangements, this cozy space is both playful and luxurious. Sip from vintage-inspired punch bowls with friends or give yourself some time to unwind with refreshing libations like the Wayward Collins with Bombay gin, pear, and honey. It’s one of the area’s true hidden gems.

Head up to the fourth floor of the Godfrey Hotel and you’ll find I|O rooftop lounge. This sprawling, 15,000 square-foot indoor/outdoor playground features a retractable roof, panoramic city views, a fire pit, shimmering water elements, a video wall, and more. Whether you’re looking to share pitchers of their signature white sangria or kick back with a simple gin and tonic, this is an ideal spot for some day drinks or a late night out. If you’re looking for a bite we recommend their lamb “lollichops” or duck quesadilla.


I|O at the Godfrey Hotel. Photograph by Jorge Gera Photography.

Beautifully perched on the 13th floor of the new Chicago Athletic Association’s hotel is Cindy’s, a rooftop restaurant and bar with a striking open-air terrace. Offering downright awe-inspiring vistas of Millennium Park and Lake Michigan, the airy atmosphere here is reminiscent of a Great Lakes beach house complete with gorgeous greenery, picnic-style seating, and indoor/outdoor spaces equipped with fire pits. Their elevated, shareable fare works perfectly in tandem with their spirit-driven beverage program. One visit and you’ll soon see why it’s one of the hottest spots to be around town.


Cindy’s. Photograph by Neil Burger.

Written By Amber Holst

Amber Holst is Vice President & Editorial Director at Concierge Preferred. A native Chicagoan, she’ll happily bend your ear about why Top Notch burgers are a must (as is an Original Rainbow Cone) and can often be found procuring milk candy in Chinatown after dim sum with her partner in crime or rooting on her beloved Green Bay Packers (yes, that’s right) at Will’s Northwoods Inn. Lover of cured meats, prosecco, and good old fashioned “slashies” she considers herself fortunate to be able to promote her hometown for a living. Fun fact? She can play the accordion.

Inline Feedbacks
View all comments
Would love your thoughts, please comment.x