From buzzy new openings to mainstays on Chicago’s outdoor drinking circuit, here’s where to imbibe during the summer months.
Windy City winters are abysmal. The light at the end of the sub-zero tunnel for long-suffering Chicagoans? A summertime escape; an opportunity to spend hours perched upon sun drenched rooftop decks drinking in the city and, of course, its killer cocktails. This summer, beloved watering holes have been upgraded and a smattering of new spots introduced. A shared characteristic? Panoramic vistas. Some with generation defining architecture, others with a tableau of authentic, urban grit. Whichever your choice, you’ll be served excellent booze with a standout view.
The Terrace at the Trump, River West
The 16th floor of the Trump International Hotel has serious wow factor. In the shadow of iconic edifices like the Wrigley Building and Louis Sullivan’s Jewelers Building, guests sip on wildly creative cocktails that change colors and have custom ice infused with esoteric ingredients (blue pea flower, anyone?) Highlights from the refreshed drink list: the gin-based Beauregard, its purple-to-blue transformation inspired by the gum-snapping Violet in Willy Wonka, and the tropical Guava Batida, made with cachaca, prosecco, fresh mint, and syrup from the new sugar cane press.
Cindy’s at the Chicago Athletic Association, South Loop
How’s this for a title: local cocktail chieftain Nandini Khaund has been annointed “Spirit Guide” at CAA’s recently opened Cindy’s, where her visually arresting drinks are just as compelling as the expansive views of Lake Michigan and Millenium Park. The vibe? Though famed design firm Roman & Williams revived this turn-of-the-century gentleman’s club into a swanky hotel, the rooftop exudes a more relaxed lake house ambiance: cherrywood tables, a library, and outdoor fire pits. Order one of the spiked punches served in carafes.
Streeterville Social at the Loews Hotel, Streeterville.
When this sprawling adult playground opens on June 25 it will be the city’s largest outdoor rooftop—and possibly its most fun. The 9,000-square-foot terrace is outfitted with two bars, a grassy lawn stocked with outdoor games (pétanque, croquet), and swinging bird cage chairs. The whimsical remixes of summery cocktails are equally playful, from rhubard mojitos to chili margaritas, as is the roster of international street snacks.
Cerise at Virgin Hotel, The Loop
If you like quirky design elements—plush yellow couches, brass moose heads—and a lively crowd of scenesters, Richard Branson’s new Virgin Hotel is your perfect summer perch. Go for the boozy teas served at two glass-topped bars with butterfly collections, local DJs, and 270-degree views of the Carbide & Carbon Building and Mies Van Der Rohe.
The Dec at the Ritz-Carlton, Gold Coast
Old-school elegance permeates this classic hotel, but the hyper-modern cocktail milieu 12 stories above Chicago’s Magnificent Mile is anything but stodgy. The Dec’s small-plates menu is entirely new, with fresh takes on traditional pub grub (duck confit nachos, sriracha aioli-accented schnitzel strips), and the classic drinks get a twist: the rum-and-rhubarb Mileena, cucumber Collins with lime-thyme soda, and boozy ice cream floats.
The J Parker at Hotel Lincoln, Lincoln Park
Towering over Lincoln Park and Lake Michigan, this retro boutique hotel is crowned by a true Windy City hideaway. The under-the-radar rooftop lounge has hipster cache thanks to chef Paul Virant farm-to-table bites and sophisticated, spirit-focused libations such as the Wise Fool, a throat-clearing combination of rye, bourbon, sherry, and fernet.
Twisted Spoke, West Town
A skeleton riding a vintage Harley welcomes bar-goers to this biker-ish joint on the West Side, where the cool crowd comes for a raucous vibe and high/low cocktails (the Bloody Mary is garnished with a whopping hunk of salami and cheese). This summer, Twisted Spoke celebrates its 20th anniversary with a Summer of Love beverage program featuring a new menu of 20 cocktails highlighting their bartender’s favorite whiskeys, housemade bitters, and more.
Kensington Roof Garden & Lounge, River North
This spot doesn’t have a view of fancy buildings (it’s atop Parliament night club) or a ritzy address (in nightlife epicenter River North). Its cool quotient comes from the fact the lounge literally projects into a vintage Chicago vignette of weathered brick buildings, graffiti and the urban chorus of the EL train. Drinks are fresh and flavorful. The food (provided by Mercadito Counter) reads like a summer playlist of classics: sliders, tacos, chips and guacamole.