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How to Drink Outside in Chicago All Year Long

By Nicole Schnitzler

Feb 6, 2019

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Cindy’s—fresh from a makeover—has million-dollar views of Grant Park and “The Bean.”

Photo by Nick Gerber; Courtesy of Cindy's

Cindy’s—fresh from a makeover—has million-dollar views of Grant Park and “The Bean.”

With amenities like curling rinks, fire pits, and igloos, these year-round rooftop bars in the Windy City can offer you much more than spectacular views.

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Rich with architectural jewels, a perfectly laid-out labyrinth of rivers, and miles upon miles of glittering lakefront, there’s no doubt about it—Chicago is a showstopping eyeful. It makes sense to find a sky-high vantage point at some of the city’s nicest rooftop bars to take it all in. Thankfully, this city has an abundance of elevated options, each with its own perks for year-round enjoyment (and more bars on the way, to boot—including this spring’s hotly anticipated arrival of The Nobel at the St. Jane Hotel). From a Fulton Market newcomer with alfresco igloos to a Mag Mile mainstay boasting Chicago’s best sunsets, these rooftops are ready to take on even the tallest order for entertainment.

Warming cabins, rooftop bonfires, and hot toddies can make outdoor evenings in winter a fun option.
Upstairs at the Gwen
Enjoy live music, ample seating, and 360-degree skyscraper views at this River North rooftop, where chef Matt Jergens spins out a range of New American dishes (from octopus al pastor to pork-belly sliders). Bring a group in the winter months for a go at its curling rink, a custom-designed perk that pairs perfectly with the bar team’s seasonal drinks. Warm up between rounds at the brand-new curling cabin, where an electric fireplace, faux furs, and holiday tunes await—along with Alpine-inspired bites like bratwurst and cheddar fondue. 521 N. Rush St., River North; thegwenchicago.com
Miracle Mile views, 24-carat cocktails, and Chicago-style pizza pockets are served atop the Peninsula Hotel.

Z Bar  

Escape the shopping chaos of Michigan Avenue with a stop at this recently opened rooftop lounge, perched on the sixth floor of the Peninsula Hotel. Saddle up at the bar for a front row show of expertly crafted cocktails from the bar team, who hold nothing back in the way of beverage pomp and circumstance (the Manhattan Royale, made with Elijah Craig 18-Year-Old Bourbon, truffle bitters, and 24-karat gold flakes, is priced at a cool $100). Chase that indulgence with even more decadence from chef Jason Xu, who puts forth wide-ranging international dishes like sushi, Sarawak satays, and, for good, local measure, Chicago-style pizza pockets. 108 E. Superior St., Miracle Mile; zbarchicago.com

Glass-enclosed domes or “igloos” are a chic solution to all-weather al fresco entertaining.


Expect epic views and seriously cool vibes at this Mediterranean restaurant, which opened in the Fulton Market neighborhood in 2018. Chef C.J. Jacobson delivers an array of familiar flavors heightened by global influences (grilled skirt steak with shawarma spice or crispy short rib hummus with sherry). Try them with any of the playful drinks from beverage director Liz Pearce, from a Winter G&T (with pomegranate and spiced cranberry) to an EVOO Martini (with corn vodka and olive oil). Summer is the sweet spot here, but don’t let the colder months scare you off—several “igloos” grace the roof come winter, kitted out with blankets, space heaters, and speakers for a cozy evening of urban chill. 302 N. Green St., Fulton Market; abarestaurantchicago.com

This Gold Coast hideaway is set on the 18th floor of the luxe Viceroy Hotel.


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Lush greenery, plenty of lounge seating, and a glimmering pool greet Gold Coast denizens and visitors alike at this rooftop bar on the 18th floor of the luxe Viceroy Hotel. Classic cocktails undergo a makeover when traditional tipples are infused with offbeat ingredients (such as a Pecan Manhattan, Passionfruit Collins, or Alpine Swizzle). Once you settle in with a drink, it’s time to peruse chef Lee Wolen’s menu, a collection of crowd-pleasing plates like beet tartare with cumin yogurt or tuna poke with crispy nori chips. 1112 N. State St., Gold Coast;  devereauxchicago.com


For unrivaled views of Chicago’s very best sights, head to this rooftop for its sweeping take of Millennium Park and “The Bean,” Pritzker Pavilion, and the expansive lakefront. Come in a group to best experience the large-format fare. Chef Christian Ragano relies on independent purveyors to inform his Midwestern-inspired menu (with options like Kilgus Farms goat Bolognese and Green Circle Farms smoked chicken). Visit on Wednesdays and Saturdays in summer to watch Navy Pier’s fireworks displays, and come early or be prepared to wait—Cindy’s draws throngs of well-heeled Chicagoans. 12 S. Michigan Ave., Grant Park;  cindysrooftop.com

Hotel rooftops dominate Chicago's high-altitude bar scene.

NoMI Garden

Located on the seventh floor of the Park Hyatt Chicago, this restaurant is an urban oasis for couples on date night, executives on lunch hour, and Windy City visitors needing a break from street-level shopping crowds. That being said, the people-watching here is as good as the sunset views, and the drinks only help matters (for a bold yet refreshing choice, try the Yuzu So Nice, with bourbon, basil, and yuzu juice). When hunger strikes, start with any of chef Eric Damidot’s seasonally driven appetizers, from carrot toast with pickled mustard seed to watermelon salad with roasted hazelnuts. Check the calendar for weekly pop-ups, too, with themes ranging from “Fried Chicken Picnic” to “Yakitori.” 800 N. Michigan Ave., Magnificent Mile; hyatt.com

A rendering of Drumbar’s freshly renovated outdoor terrace, which pairs architectural style with postcard-perfect Chicago views.


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Clubhouse vibes and speakeasy-caliber cocktails collide at this rooftop bar, where beverage director Gary Matthews curates a globally inspired drinks list. Head south of the border with the Tea Time in Chile, a fresh take on a French 75 with pisco, earthy masala chai, and bright pops of pear cider, or jump across the pond with the Bergamot Quince Gimlet—made with gin, scotch, and citrus, it manages to be smoky and tart at the same time. If weather permits, enjoy them al fresco, where a just-renovated outdoor terrace offers vistas of Lake Michigan and the Hancock Building. 201 E. Delaware Pl., Gold Coast; drumbar.com

Head to Raised for a sky-high perch overlooking the Chicago River.


This high-rise haven rests directly over Wacker Drive, meaning it offers some of the best glimpses in town of the meandering Chicago River. Enjoy them in comfort and style thanks to the space’s many thoughtful touches, including fire pits, cabanas, and plenty of lush greenery. Kick things off with a round of drinks (namely the Purple is to Lavender, with Hendrick’s gin, lemon, and lavender), then delve into gussied-up gastropub favorites, such as truffle fries and lobster rolls. Save room for dessert—the s’mores are a surefire way to please anybody, any time of year. 1 W. Upper Wacker Dr., The Loop; raisedbarchicago.com

Views, Mediterranean cuisine, and happy hour specials bring afterwork crowds to Torali.

Rooftop at Torali

Seasonal Italian cuisine and an Old World-leaning beverage program are the focus of this downtown retreat on the 12th floor of the Ritz-Carlton Hotel. Enjoy all-encompassing skyline views while sipping some of the handiwork from the bar team, like the Aperol Spritz, coupled with elderflower and lavender here. Build up an appetite for the substantial fare from chef Baasim Zafar, who serves up hearty fixes of polenta fries, meatball sliders, and Calabrian pepper chicken wings nightly. Post-work revelers should join in for Wednesday happy hours, when they can grab glances of the sunset alongside $1 oysters and $10 glasses of rosé. 160 E. Pearson St., River North; toralichicago.com

Art deco touches and views of neighboring architectural landmarks abound at the LH Rooftop.

LH Rooftop

This always-buzzing penthouse bar consists of three levels—but on sunny days, folks will want to head straight to the 22nd floor. It’s here where a sprawling outdoor rooftop welcomes guests for sunset views, lounge seating, and art deco details (a nod to the 23rd floor’s 1923 Beaux-Arts cupola). Ready yourself for Jazz Age cocktails and reimagined American cuisine, which chef Jacob Verstegen brings to life in plates like smoked pumpkin pâté and a white-bean sausage. Those offerings are just as exciting in winter, when the rooftop hosts a monthly Nordic dinner series featuring guest chefs, faux furs, and five courses reflecting Scandinavian flavors. 85 E. Wacker Dr., New East Side; londonhousechicago.com

>>Next: The 9 Best Spots for Pizza in Chicago

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