Chicago's Best Rooftop Date Spots 2019
Rooftops grace Chicago's most notable eateries and offer 360 degree views of Lake Michigan and the city skyline. These charming spaces bolster your appreciation for this city – and the one with whom you share the experience. In other words, rooftops are damn romantic. Plan your next date with this carefully crafted list.
Fountainhead's rustic rooftop garden features a bar that cycles in and out of 20-plus craft beers and artisanal snacks from chef Cleetus Friedman. Its high-quality, inventive menu is designed to complement a comprehensive yet distinctive selection of beers, wines, whiskys and spirits. There's a special emphasis on local and regional craft beers and artisanal foods that appeal to even the most discriminating connoisseurs.
Address: 1970 W Montrose Ave, Chicago, IL 60613
GENE'S SAUSAGE SHOP & DELICATESSEN
Besides being an awesome delicatessen and a great place to get German culinary delights, Gene's has one of the sunniest most enjoyable rooftops in Chicago. You can enjoy sausages and pints atop this quaint German beer garden while overlooking Lincoln Square. Get ready to line up now because the local favorite does get packed. Make sure to pick up some meats, fresh pretzel rolls and homemade salads from the downstairs deli on your way out.
Address: 4750 N Lincoln Ave, Chicago, IL 60625
THE J. PARKER
Located in Hotel Lincoln, The J. Parker offers some of the most spectacular views of Lake Michigan and the Chicago skyline. Grab a signature cocktail and check out the food menu crafted by Paul Virant, Chef and Owner of Perennial Virant. Seating can be tough if you show up on a beautiful weekend so get there early to reserve a spot!
Address: 13, 1816 N Clark St, Chicago, IL 60614
This 120-person sleek rooftop is perfect for those wanting to bask in the sun with a come-as-you-are vibe. Baseball fans will enjoy the three large-screens; there's even some green ivy reminiscent of the North Side baseball stadium. The whiskey selection boasts 115 whiskeys, from standards like Bulleit and Old Overholt to standouts like Lock, Stock and Barrel 13-year. There are single-malt scotches all the way up to Laphroaig 25-year, Irish whiskeys, ryes, bourbons and whiskeys from Japan.
Address: 1367 N Milwaukee Ave, Chicago, IL 60622
NEAR NORTH SIDE
DrumBAR was formerly the Hampshire House – a building used to house nursing students during World War II. After converting the apartments into today's Rafaello Hotel, they promoted the top 18th floor (where drumBAR sits now) as the ultimate penthouse “with 24 foot ceilings, two bedrooms, formal dining rooms, a paneled office with a bar hidden by moveable bookcase and of course, the outdoor terrace with views of Lake Michigan.” While you can still get a sense of history in drumBAR, the terrace successfully helps keep one foot in the past and one in the present with a comfortable, relaxing spot to sip cocktails.
Address: 201 E Delaware Pl, Chicago, IL 60611
SHANGHAI TERRACE AT THE PENINSULA CHICAGO
The Peninsula’s Shanghai Terrace is a rare commodity perched atop a swank downtown hotel. The dim sum is the best outside Chinatown, followed by traditional Cantonese desserts like sweet almond broth and bird’s nest soup perfect for pairing with cocktails almost too pretty to drink. With a hushed lantern-lit intimacy, it creates the perfect date night setting. Extra bonus: The staff shower you with your choice of pashminas if the evening does become a chilly one, allowing you to lounge in peace that much longer.
Address: 108 E Superior St, Chicago, IL 60611
VERTIGO SKY LOUNGE
This indoor-outdoor lounge-hybrid thrives year-round. Soaring 26 stories above the city, jaw-dropping views of the city are part of the package, complete with an outdoor fire-pit and nightly DJ. In the winter, the lounge turns into the city's only Outdoor Rooftop Ice Bar.
Address: 2 W Erie St, Chicago, IL 60654
IO URBAN ROOFSCAPE AT THE GODFREY HOTEL
Chicago’s largest indoor-outdoor lounge offers unobstructed skyline views for 330 guests: 100 indoor and 230 outdoor. The outdoor greenhouse-like space has a year-round sundeck that comes fully loaded with a retractable roof, waterwall, large fire pit, and cabana rentals. Pro tip: Try the margarita–– though the menu lists four ingredients, there are actually twenty-two that make up the drink, including citrus elements, shrubs, and a habanero salt foam.
Address: 127 W Huron St, Chicago, IL 60654
Tanta's rooftop is a Peruvian escape with one of the best Pisco Sours in town. If your craving seafood, Chef Gastón Acurio crafts a must-try ceviche dish. The sleek, modern space is date-friendly, though you'll need to plan ahead since it's always busy.
Address: 118 W Grand Ave, Chicago, IL 60654
Set in a vintage River North building, this swanky hangout features three levels, each with a different menu and ambiance. However, our favorite is the Venetian-style rooftop with Louis Sullivan tile, ivy-covered walls, and specialty cocktails. The space seats 85 and the menu focuses on punch bowls as well as seasonal cocktails. High walls seclude this rooftop from busy Hubbard Street making it the ideal urban escape for summer imbibing.
Address: 111 W Hubbard St, Chicago, IL 60654
Little Goat is the West Loop's resident retro diner equipped with its very own intimate rooftop. When you dine alfresco, you'll enjoy its quaint bar, cozy lounging, laid-back atmosphere, and view of the Sears Tower to the east and Randolph Street to the west. Goat-liver mousse is just one of the specialty bar snacks served from the rooftop bar. Grab lunch in Little Goat Bread and enjoy it rooftop or wait until the evening for the bar to open.
Address: 820 W Randolph St, Chicago, IL 60607
More of a gigantic playground than a simple rooftop lounge, Streeterville Social features a patch of grass where guests can play bags or topple an oversized Jenga set. Not looking for fun and games? The rooftop’s bar features a street food-inspired menu and creative cocktails.
Address: 455 N Park Dr, Chicago, IL 60611
DECA AT THE RITZ CARLTON
Just off the 12th floor lobby of the Streeterville Ritz-Carlton, this French brasserie provides an art deco–inspired setting for a wide range of fresh, well-prepared fare along with handcrafted cocktails, craft beers, wine and champagne.
Address: 160 E Pearson St, Chicago, IL 60611
THE SIGNATURE ROOM AT THE 95TH
Massive floor-to-ceiling windows and 360-degree views of the city provide an atmosphere that can’t be beat. And with $16 tater tots and $150 pours of Remy Martin Louis XIII, you’re gonna pay for it. Pro tip: Hang in The Signature Lounge rather than the white-tablecloth dining room, where prices are a bit less steep, though not by much.
Address: 875 N Michigan Ave, Chicago, IL 60611
The rooftop restaurant-bar at the Chicago Athletic Association Hotel offers panoramic views of Millennium Park, The Art Institute, and Lake Michigan. Alongside the sweeping beer and wine list lies potions and elixirs to "cure your ills with creations from the bar, the original pharmacy."
Address: 12 S Michigan Ave, Chicago, IL 60603
Plymouth Restaurant & Bar is a popular post-work hangout with a third floor rooftop. Flanked by John Marshall Law School and the Harold Washington Library, the rooftop runs year-round courtesy of an enclosed heated patio that's more working man and less typical downtown swank.
Address: 327 S Plymouth Ct, Chicago, IL 60604
HOMESTEAD ON THE ROOF
This 80-seat rooftop restaurant keeps getting more and more appealing. It has an outdoor fireplace, pergola with a retractable roof, and a rooftop vegetable and herb garden. Chef Chris Davies and the formidable Chris Teixeira still oversees the breads and desserts. While you're in the neighborhood, check out Happy Village to play ping-pong in their beer garden.
Address: 1924 W Chicago Ave, Chicago, IL 60622