6 Chicago destinations for a poolside hang with great food

By Nicole Bruce

Here in Chicago, we've been longing for the return of hot, sun-drenched days since, well, last summer. So it’s only natural to reel in those vacation vibes by taking dips in some of the city's best swimming pools—with a drink in hand. To complete this picture of paradise, we've scoured the scene for pools that also happen to have some enticing provisions for your noshing pleasure, so you'll never have to abandon that hard-earned lounge chair. Now go scurry to some of these hot spots for a serious cool down while you can.

Kimpton Hotel Palomar Chicago
Regally perched on the 17th floor, the glass-enclosed rooftop terrace with heated pool at Hotel Palomar offers refreshing city views year-round. Guests can order from the special al fresco terrace menu, which features beers and seasonal cocktails as well as elevated bar snacks and light dishes, including salads with seasonal veggies and three cheese grilled cheese sandwiches with Mornay sauce. New American gastro-lounge Sable Kitchen & Bar will even deliver their creative dishes—think vegetables sourced straight from the garden, fresh fish, luscious meats, and show-stopping cheeses—to poolside chaises upon request.
Neighborhood: Near North MAP

Loews Chicago Hotel's Streeterville Social
Loews Chicago Hotel's expansive rooftop lounge, Streeterville Social, is a prime spot for post-work gatherings, late night lounging, and al fresco dining with city and skyline views. The outdoor space surrounds a 75-foot enclosed pool, and features two distinct dining experiences: The Bistro, a sit-down restaurant which offers weekly specials like the $5 house margarita in true Margarita Monday fashion; and The Event Terrace, a lively outdoor space where you can host a private outdoor event for a group of up to 600 guests. Both spots serve up a serious taste of summer, so we recommend making the most of it while you can.
Neighborhood: Streeterville MAP

Soho House Chicago
Soho House Chicago's laidback rooftop with a sleek, heated pool and outdoor fireplace is launching its new food and beverage concept for the summer. Middle Eastern restaurant Nava will be serving up light, flavorful dishes like house-made hummus, baba ganoush, and beet labneh dip, wood-fired asparagus and goat cheese sumac flatbread, and sea bass wrapped in grape leaves. And to really take advantage of the panoramic skyline and pool, book one of the 40 rooms at this historic warehouse hotel in the West Loop.
Neighborhood: West Loop MAP

The Peninsula Chicago
After some invigorating laps in The Peninsula Chicago's pool, where floor-to-ceiling windows overlook Michigan Avenue, you can enjoy poolside sips and snacks while reclining in extra-cushy lounge chairs on either the pool deck or adjoining sun deck. Menus are at the ready for orders of seared tuna Niçoise salad, grilled sirloin burger, or the Maine lobster roll with tarragon, celery, and pickled vegetables, not to mention cool treats like raspberry or passion fruit sorbet. Just book at least two hours of spa appointments (who couldn't use a massage or pedicure?) to get a day pass to the pool.
Neighborhood: The Magnificent Mile MAP

The Robey's Cabana Club
Embrace Chicago's summer season at the Cabana Club, Wicker Park's newest rooftop hangout, which stretches atop The Robey and Hollander hotel complex. While the pool is limited to hotel guests, club patrons can still sunbathe on the 160-seat poolside deck, or sip on cocktails inside the 60-seat lounge. The neighborhood's tallest building offers 180-degree skyline views, Mexican-inspired drinks like micheladas and palomas, and casual Latin bites like shrimp and octopus tostadas and hand-held skewers.
Neighborhood: Wicker Park MAP

East Bank Club
Spanning 60,000 square feet, this rooftop deck in River North boasts two outdoor pools—one for adults only and one for families—a full bar with tropical drinks, and a café with a grill. Guests of the coveted sky deck can order blackened chicken wraps, griddled seafood tacos with lime-cilantro slaw and queso fresco, and smoothies loaded with pineapple, mango, coconut, and vanilla frozen yogurt.
Neighborhood: River North MAP

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