8 Chicago Hotels with Rooftop Pools, Restaurants, and Bars

The Robey hotel is housed in a famous historic Chicago building in the Wicker Park neighborhood. The art-deco landmark building formerly known as Northwest Tower is now a luxury hotel, complete with a rooftop lounge and pool.

The Cabana Club on the 6th floor offers 180-degree views of the skyline. Its location in a western neighborhood, set away from downtown, makes the view unique. Not only will you see the famous skyscrapers that make the city’s architecture famous, but also the neighborhoods and train lines that make it run.

Relax in a poolside cabana chair, or take a dip in the pool yourself. Drinks are on the tropical side, and there’s a small food menu as well featuring pita and hummus, mixed nuts, and other snacks.

A beachy vibe in a historic building sounds odd, but it works. Come summer, the Robey is the place to be.

For a tranquil, spa experience in the sky, head to Eurostars Magnificent Mile (formerly Dana Hotel and Spa), a four-star, boutique hotel in downtown Chicago with one of the swankiest rooftops in the city. On the 26th story, find Apogee, a garden rooftop lounge with plush furniture, potted plants, fire pits ensconced in glass, and craft cocktails delivered in a gorgeous presentation.

The menu comes from cocktail master Benjamin Schiller, and the seafood-inspired food menu is in partnership with Fifty/50 Restaurant Group. By day, sip coffee or mimosas with views over glass walls of the skyline. By night, dance to some of the city’s hottest DJs under the stars.

Every Chicago hotel rooftop has a nice view, but Londonhouse Chicago, located right off Michigan Avenue, might be the best. From one side, look over the Chicago River to the Wrigley Building and Tribune Tower, both architectural masterpieces. From another angle, see the Marina Towers and wrought-iron bridges that open and close over the river. No matter where you look, you’ll see sweeping views of iconic Chicago scenes.

Sip champagne or flowery cocktails and enjoy light bites in low-lounge seating or at high-tops throughout the roof, or find some shade under an umbrella or the covered bar. On the second level, there’s a cupola reminiscent of ancient Athens or Rome. Reserve the table inside for special events.

By night, the relaxed lounge turns into a party bar with a DJ and dancing and long lines. Get here early to claim your spot.

If you’re looking for a rooftop where you can have a nice meal, look no further than Conrad Chicago. Rooftop restaurant Noyane serves better food than most rooftop bars, plus its location in the Gold Coast means views over historic mansions and with the skyline to the south.

Noyane (hidden roof in Japanese) is decked out in subdued hues and comfy white couches. The atmosphere invites you to come in and relax, and the large sake and Japanese whiskey selection give you a reason to stay awhile. Order drinks and appetizers in the lounge area, or dine on high-end Japanese food on the patio.

The rooftop isn’t only for warm weather. There are an interior restaurant and lounge, too. Baptiste and Bottle have one of the city’s largest whiskey collections, cozy furniture perfect for settling in on a winter night, and floor-to-ceiling windows to maintain the city views.

Calling all baseball fans! Zachary is a new hotel (opened in late 2018) in Wrigleyville with a rooftop offering clear views of Cubs games. It’s like the best seat in the house at Wrigley Field, without the crowds.

The rooftop has a high-end sports bar feel. Modern, velvety seating is matched with historic sports photos and a cozy fireplace. There’s local beer, cocktails, and elevated bar food including pizza and Big Star tacos. The rooftop is covered, so you can enjoy it in all seasons, but has a ledge open in summer months where you can look out to watch the game.

Planning a celebratory trip? Head to Peninsula Chicago, where the drinks are gold-flecked and the service is impeccable. Z Bar looks over Michigan Avenue, so you feel like you’re in on the action without any of the crowds or hassle. Listen to live music by candlelight during an intimate dinner, or while lounging on low-slung couches.

Try a spin on a classic cocktail, like the Manhattan Royale, that uses small-batch bitters you can’t find anywhere else in the country, or go for the Spirit-Free Spritz with seedlip garden, bitter syrup, and soda. Too early in the day for a cocktail? There’s also a collection of rare teas such as Sicilian blood orange pu’erh and Z Bar chrysanthemum dream.

As one of the city’s most luxurious hotels, it’s fitting the rooftop matches that aesthetic. Dress accordingly (smart casual), and come with something to celebrate—even if that’s simply being out in the city on a summer night.

Looking for a hotel that’s trendy and fun, but on the casual side? The Waydown Rooftop Bar at the Ace Hotel in West Loop is perfect for you. It’s stylish, but relaxed—the kind of place you can go before a night on the town or for casual afternoon drinks.

Like much of the former warehouse district, the bar has an industrial vibe. Woods and metals make up the interior, which has an inside section with large windows that bring in splashes of sunlight, and a large outdoor patio for warmer months. The name, Waydown, comes from a melancholic song by Illinois native John Prine. The hotel pays homage to him through nightly music from local and national acts.

Drinks are classic—old fashioneds, Manhattans, and the like—and very good. The food menu is small but filled with snackable, addictive things like spicy candied cashews, hot fried chicken nuggets, hummus, and other bar foods.

Be in the center of it all with 360-degree views of the entire city at AIRE, the rooftop bar in Hyatt Centric. Take the elevator straight to the 24th floor, where you’ll be met with an airy patio decked out in light colors, deck chairs, umbrellas, and flowering potted plants. Here, you can order cocktails and food items such as flatbreads and salads off of a small menu.

The main thing this rooftop has going for it is the views. When they say 360-degrees, they really mean it. From the hotel’s location in the Loop, you can see the skyline from every angle. Do a lap around the bar to make sure you take it all in. For a garden in the sky with fantastic views in every direction, this is your spot.