As the smell of pumpkin spice starts wafting out of every local coffee shop, plaid shirts begin to reappear, and ghoulish Halloween decorations arrive on stoops, there can no doubt that fall has finally come to Chicago, bringing with it that familiar desire to enjoy the last warm days of the year and savor the crisp outside air, before retreating indoors for the window. And there’s no better way to do that than from a rooftop retreat in a luxury condo.
If you’re looking for an apartment anywhere from the North Shore to the Loop, look first to Related Realty for insights into every niche and neighborhood. This Chicago real estate brokerage firm has a long history of connecting clients with select homes featuring amenities and fine touches such as state-of-the-art appliances, inspired decor, inviting communal spaces, and, of course, gorgeous rooftops.
At luxury rentals such as Related Midwest property 500 Lake Shore Drive, minutes from River Esplanade Park and the Museum of Contemporary Art Chicago, you can sip hot chocolate and look out across the city from the roof deck, which also features a swimming pool for the warmer months. In the Streeterville neighborhood, Related Realty is also the exclusive leasing agent of the boutique apartments at Sienna Flats, where you can leave your oak-floored, high-ceiling abode in this new residential retreat, and take the elevator to the inviting rooftop deck, which boasts stunning views as well as outdoor grills that are perfect for a late-autumn cookout.
Although such home-based rooftop escapes are always enjoyable, the Windy City offers its fair share of sophisticated rooftop bars where you can relish additional sky-high views while indulging in cocktails and some tasty fare with family or friends.
Cindy’s | 12 South Michigan Avenue
You’ll be tempted to take non-stop photos during a visit to Cindy’s. The food, people, and vistas are all reasons why the Chicago Tribune calls the restaurant “breathtakingly gorgeous.” Perfect for groups, this bright, breezy space atop the Loop’s staid Chicago Athletic Association Hotel boasts panoramas of Millennium Park and the lake beyond. At 13 stories above the city, you can easily get to “sea level” by ordering one of Cindy’s signature cocktails: the Aegean Sea, a one-of-a-kind drink with gin, caper leaves, and pinecone sap from the Alps.
Drumbar | 201 East Delaware Place
For those who have more classic tastes but still seek a lofty lookout, Drumbar serves up top-shelf traditional favorites such as scotch and bourbon as well as superbly mixed tropical drinks like the Ximenez margarita. This rooftop bar at the top of the Raffaello Hotel in the Gold Coast neighborhood offers a sunny patio as well as an indoor section where you and your crystal-clear, artisanal ice cubes can stay cool.
LondonHouse Rooftop | 85 East Wacker Drive
Not long ago, performances by jazz luminaries like Dave Brubeck, Cannonball Adderley, and Nancy Wilson at the London Guarantee Building drew Chicago’s elite sophisticates to this Michigan Avenue landmark. After a recent renovation, the newly branded LondonHouse Hotel is drawing new crowds from the crème de la crème of the city’s cultural scene with its three-story rooftop bar and lounge. Turquoise barstools pop against the sleek, muted ambience of the indoor first level where you can enjoy signature cocktails like the Dearborn—a citrusy craft beer-based concoction that’s perfect for summer. On the terrace, sip champagne and enjoy singular views of the river as you indulge in the daily mimosa bar.
Streeterville Social | 455 North Park Drive
Satisfy your yen for craft beer and lawn games via a quick trip to the Streeterville Social on top of the Loews Hotel. With 9,000 square feet of swing chairs and grass-covered areas in Chicago’s largest terrace, this unique space is where “your inner child can roam free while still enjoying tiki-inspired cocktails,” as one Zagat review notes. How much more “Chicago” can you get than eating a sausage and drinking a pint of Goose Island on a rooftop overlooking the John Hancock Center?
In-the-know homebuyers are making the “Second City” their first choice for setting down roots and enjoying stunning rooftop views—at home and out on the town.