Best Places for Outdoor Dining in Chicago
Credit: Courtesy of The Peninsula Chicago

In Chicago, the definition of “warm” is open for discussion. Unlike L.A. or Miami, we don’t need sundress weather to eat outside. The minute that the temperature tops 50, tables are out, umbrellas are installed and and al fresco dining season commences. We may need heat lamps, but no matter. If it’s bearable (remember, we have survived the polar vortex), Chicagoans will brave the elements. Another thing: We are not picky about the exterior ambiance. A chic, shrub-filled patio is great. A rooftop urban oasis is fabulous. But, we are also just as happy noshing at a table plopped down unceremoniously on a city sidewalk. So, where are the best bets around the city? It depends on your mood. For romance, nothing tops the picturesque perch of North Pond Café. For a hipster vibe, hit The Dawson. For steakhouse fare that perrfectly complements its stellar people-watching, book Gibson’s. And for classic Italian that never disappoints, go to Vivo.

The Dawson

Tracking down that authentically cool, off-the-grid restaurant can be tricky. To make like a local, head to West Town, where this former fireplace-mantle factory turned neighborhood boite beckons with craft-oriented cuisine, such as chicken-fried lobster abd honey-brined pork chops and killer cocktails, such as the Bayonet, with gin, watermelon, tarrgaon and sparkling wine. There are two levels for outdoor dining.

North Pond

Enjoying cuisine by James Beard Award-winning chef Bruce Sherman’s at this restored “warming house” for ice skaters in Lincoln Park, and gazing up at the Chicago skyline, is an incomparable experience. Though not technically outside, with the French doors thrown open, this restauarnt on the edge of a pond feels positively al fresco.


Whatever the season, Gibson’s is Chicago’s ultimate steakhouse. The outdoor section of this restaurant (outfitted with ceiling heaters, natch) is perenially packed with A-listers, executives and sports elite. Why? It’s the orgy of marvelously marbled prime ribs, charred chops and colossal lobster tails. Not to mention the mountains of creamed spinach, the massive martinis and the exceptional service.

Shanghai Terrace

Tucked inside the Peninsula Hotel, Shanghai Terrace is a true urban oasis. While enjoying upscale Pan Asian specialties such as dim sum, BBQ pork buns and Peking duck, you’ll also be treated to a visual feast: stunning panoramic views of the iconic Chicago Skyline from the vantage point of Michigan Avenue.