Chicago's 10 Hottest Rooftop Scenes

By Sarah Freeman  |  May 11, 2015

Spring is here, so don’t waste another minute eating and drinking indoors. Here are 10 of the most stunning rooftops in Chicago for alfresco dining and imbibing.

  • Celeste

    This Venetian-style rooftop, decked out with Louis Sullivan tile and ivy-covered walls, offers a seasonally inspired drink menu, including frozen concoctions and large-format cocktails served in vintage punch bowls.

    The View: High walls seclude this rooftop from busy Hubbard Street, making it the ideal urban escape for summer imbibing.
    What to Drink: One of the frozen creations is a Nuclear Caipirinha, with overproof Leblon Cachaça, Velvet Falernum, Green Chartreuse and lime.
    Insider Tip: Once a month, the rooftop hosts Made in Brazil, an evening dedicated to Brazilian food, drinks and live entertainment.

    111 W. Hubbard St.312-828-9000

  • Cerise

    Twenty-six floors above The Loop, the city’s newest rooftop bar serves craft cocktails and an izakaya-inspired menu. It wraps around three sides of the historic facade of the Old Dearborn Bank Building, which now houses Virgin Hotel.

    The View: Straight-on Chicago river and skyline, including Trump Tower.
    What to Drink: Tradewinds Punch, which is a potent mix of El Dorado 151 rum, Bombay dry gin, grapefruit, guava, lime, vanilla, saffron and IPA.​
    Insider Tip: This is the place for a party, with a DJ spinning in the main bar on most nights.

    203 N. Wabash Ave.; 312-940-4400

  • The Dec

    The Ritz-Carlton Chicago's rooftop bar and lounge offers handcrafted cocktails, craft beers, wine and champagne as well as a menu consisting of small plates from duck confit nachos to mahi mahi ceviche.

    The View: A concave mirror instillation reflects the sleek lounge that is tucked in between soaring skyscrapers.
    What to Eat: One of the essential summer dishes is the bucket of chocolate-covered ice cream bonbons — a close second is the trio of mini ice cream sandwiches.
    Insider Tip: Every Thursday, "Get Your Shuck On" with an assortment of freshly shucked East and West Coast oysters, while Sunday is a "Funday" with boozy floats and ice cream desserts.

    160 E. Pearson St.; 312-573-5160

  • Drumbar

    This popular rooftop returns for its third season under the guidance of new bar manager Whitney Morrow​, who's serving a seasonal selection of craft cocktails in the elegant marble-covered bar with wood and leather accents.

    The View: An up-close-and-personal view of the Hancock Building.
    What to Drink: My Little Lotus, made with St. George dry rye gin, Jepson’s Malört, lemon juice, grapefruit, black pepper rose grenadine and cracked black pepper.​
    Insider Tip: On the weekends, the scene is more booming nightclub than cozy cocktail lounge.

    201 E. Delaware Pl.; 312-933-4805

  • Homestead

    This seasonal restaurant takes the farm-to-table movement seriously, with a rooftop garden that inspires both the food and drink menus.

    The View: No need to look far for a scenic landscape; the centerpiece of the rooftop is a lush garden that continues up the walls on trellises.
    What to Eat: Egyptian-spiced mussels are a year-round favorite.
    Insider Tip: Even when the weather is bad, don’t dismiss this dining destination; the indoor area serves the same menu in the rustic bar and dining room.

    1924 W. Chicago Ave.; 773-645-4949

  • I|O Urban Roofscape

    Chicago’s largest indoor-outdoor lounge and bar space offers year-round, unobstructed south-facing skyline views for 330 guests — 100 indoor and 230 outdoor.

    The View: Turns your eyes to the sky with the retractable rooftop that opens up to showcase nearby skyscrapers.
    What to Drink: The house mojito starts with rum that's been infused with mint over low heat for three hours to create a vibrant, fresh taste. It's combined with housemade lemon-lime soda made with Tahitian vanilla-bean syrup.
    Insider Tip: Stopping in late-night? Better dress to impress. An "upscale casual" dress code keeps the crowds classy.

    127 W. Huron St.; 312-649-2000

  • The J. Parker

    We dare you to be in a bad mood with a cocktail in hand here, overlooking lush views of Lincoln Park. House drinks focus on refreshing flavors, perfect for sitting in the chic fireside lounge area.

    The View: Pick your vista from Lake Michigan, Lincoln Park or the Chicago skyline; the patio offers unobstructed views of all three.
    What to Eat: J. Parker Burger, featuring dry-aged beef, butterkase cheese, "belly fire" mayo, lettuce, charred onion and pickles.
    Insider Tip: A recently installed retractable glass enclosure means that this rooftop can transition from an alfresco party to a covered bar in less than five minutes in the event of a sudden downpour.

    1816 N. Clark St.; 312-254-4747

  • Soho House

    If you can get in, this is the rooftop for the see-and-be-seen crowd this summer. The sixth floor of the members-only club features a pool, two full bars and a restaurant specializing in wood-fired pizzas as well as breakfast and weekend brunch.

    The View: Sitting on the eastern edge of the West Loop, the rooftop looks towards The Loop with views that nearly stretch to the lake.
    What to Drink: Grab a lounge chair and a flute filled with the French 99, a bubbly combination of Medley Brothers bourbon, grapefruit, demerara and Prosecco.
    Insider Tip: Members are allowed to bring guests, so if you don't want to spring for the several-thousand-dollar membership fee, get friendly with an existing member.

    113 N. Green St.; 312-521-8000

  • Tanta

    This Peruvian escape is complete with two bars, one of which specializes in pisco and another that specializes in raw seafood.

    The View: An urban paradise nestled among the brick buildings and stone facades of River North.
    What to Eat: Ceviche sliced to order — try the "Classico": fluke, red onions and cilantro served with lime and aji.
    Insider Tip: Reservations aren't taken for the rooftop, so it’s a popular alternative when the dining room is crowded, which it usually is.

    118 W. Grand Ave.; 312-222-9700

  • Terrace at Trump

    A rooftop for Chicago's rich and famous, located off the 16th-floor Bridges Room, guests with deep pockets find themselves surrounded by the metropolitan oasis with custom-designed lounge, booth and table seating surrounded by urban beauty.

    The View: Sit here at sunset when pinks, reds and oranges reflect off the all-glass building paint the Wrigley Building that sits across the river.
    What to Drink: This summer the bar breaks out a sugarcane press to make drinks such as the Guava Batida with Cabana Cachaca, guava purée, fresh cane syrup and lemon topped with Prosecco.​
    Insider Tip: For the ultimate luxe experience, opt for the 100 Dollar Sundae featuring 20 scoops on a Lazy Susan with a rainbow of toppings from milk chocolate Rocher to strawberry pearls.

    401 N. Wabash Ave.; 312-588-8600