For Chicago thrill-seekers, the sky is no limit

Rooftop venues offer great views, fun and games

Remember when you’d open the front door, walk out and be greeted by the warm, moist air of an endless summer? Remember no more. It’s upon us. The windows are open and there’s a wistful scent in the air. The faces passing by seem softer with smiles that come easier and last longer. The pulse of Chicago life has relaxed into an easy, rhythmic beat. Can you feel it?

It makes you want to get away from it all—float above the city skyline, have a drink (or two) with good friends, relax a little and laugh a lot. Fortunately, you live in the right place. Chicago’s cityscape is the envy of the nation. In fact, with 130 buildings reaching more than 492 feet, Chicago is No. 2, only behind New York, on the list of U.S. cities with the most skyscrapers.

It’s why so many Chicagoans will tell you, what’s great on the ground is even better 20 (or 30?) stories up. Area hotels, sports venues, restaurants and other businesses have received the message, high and clear, adding to an ever-growing list of rooftop wonders across the city.

Rooftop dining and libations

Breathtaking views, sky-high seating and unbeatable panoramic vistas that last for miles are taking eating out to new heights. Some venues even add a selection of favorite games (Whirlyball, anyone?) to level up the open-air experience between bites. Cornhole, Giant Connect 4, billiards and shuffleboard all take on a new sense of urgency when suspended (safely) over the streets of Chicago.

Amazing new venues are opening to a fresh salvo of superlatives as they seek to find their rightful place among the previously unparalleled, panoramic views of mile-high terraces, lounges and patios that ornament the Chicago sky.

Offshore Rooftop & Bar, which opened in 2019, is perched atop Navy Pier’s Festival Hall and listed by Guinness World Records as the largest rooftop bar in the world. In true Navy Pier style, the all-season and all-weather venue offers a unique perspective over the greatest of the Great Lakes.

Not to be overshadowed, Kennedy Rooftop, which opened in 2020, rests comfortably above the Hyatt Place Chicago Wicker Park. The venue overlooks the vibrant and diverse Wicker Park neighborhood and beyond—way beyond. “Here, where North Ave. and Ashland Ave. meet,” they proclaim, “we have created an urban chic rooftop to celebrate the people and the city.”

And hats off to Chicago’s newest vaulted sky bar to open for the season, AIRE Rooftop Bar, open in May. The amazing escape from the streets sits 24 stories up on top of the Hyatt Centric The Loop Chicago. AIRE’s dazzling 360-degree view is flanked on the entire east, west, and south facing walls by the striking, new backlit mural designed by internationally acclaimed artist, Onur.

But that’s just the tip of the skyscraper. If you can’t decide among Chicago’s many rooftop watering holes, you may not have to. MPC events has scheduled a series of five rooftop bar crawls this summer. Parachutes not included.

Rooftop ballgames

You may have been told the best seats at the ballgame are behind home plate. You were told wrong. Since the ballpark opened in 1914, baseball fans have been clamoring for the rooftop seats around Wrigley Field.

Places like Wrigley Rooftops and Wrigley View Rooftop will hook you up with an all-inclusive rooftop baseball experience including views of historic Wrigley Field that will impress even the most devoted Cubs fans. Sipping or gulping from sky-high tumblers, dining on catered cuisine and gawking over the amazing view, the only thing you’ll wish for is that you had done it sooner.

Rooftop movies

Popcorn? Check. Rooftop seating? Check. That’s right, now you can experience dinner and a movie five floors up with nothing but stars above. Rooftop Cinema Club, which opened in May, promises city skylines, sunsets, starlit evenings, awesome drinks, delicious food and great movies on the big screen—all from the rooftop terrace of The Emily Hotel. Order classic cinema concessions or choose from a full food and bar menu throughout the film. Wireless headphones and LED moving screening cinch the deal.

Check our social feeds for more of Chicago’s hottest rooftop wonders.