6 Chicago Hotels with Picture-Perfect Rooftops

Heated pools and even hotter crowds. Now mix that with ice-cold cocktails to keep the conversations flowing, and picture-perfect views to fill up your entire Instagram. That’s just some of the things you can experience at the top of these Chicago hotels.

It’s no surprise that hotel rooftops have become some of the most coveted hotspots in the Windy City. They are perfectly positioned to give both locals and travelers a unique vantage point of the city’s iconic skyline. 

Most recently, Chicago has become a hub for understated luxury hotels, all trying to top one another (almost literally) with their rooftop restaurants, cocktail bars, and cabana lounges. It’s in these rooftops where Chicago’s stylish hotel renaissance meets the centuries-old architectural spirit. 

Here’s what it’s like at the top.

Cabana Club at The Robey 

The one-year-old hotel in Wicker Park is comfortable and understated in all the right places, with just enough industrial touches to infuse it with a cool-modern look.

Up on the sixth-floor rooftop, things get a little wilder. To make the most of this Art Deco skyscraper, the hotel includes a rooftop pool lounge open to the public. Known as the Cabana Club, this is a precious slice of paradise in the middle of a thriving urban jungle. 

The Rooftop at the Soho House Chicago

Located in the warehouse-hip Fulton Market District, the Chicago outpost of the world-famous members-only club has one of the most coveted rooftops in the city.

Heard about those chilly days in Chicago? The Rooftop at the Soho House will keep things hot, with a heated pool and outdoor fireplaces. To check it out, become a member or befriend one. You can also book a room at the hotel to enjoy all the member-only spaces.

Cindy’s at Chicago Athletic Association Hotel

This rooftop restaurant and open-air terrace overlooks Millennium Park and Lake Michigan. And it’s more than just a pretty view.

Come for weekend brunch and enjoy some avocado toast, a breakfast burrito or buttermilk pancakes with elderflower crème fraiche. And don’t forget a cocktail, or a sunrise potion, as they call it.

Cerise at the Virgin Hotel

Some rooftops continue to be hotspots well after the sun goes down. That’s definitely the case with Cerise, the stylish rooftop lounge at the Virgin Hotel.

Centrally located right in The Loop, Cerise attracts a vibrant mix of locals and guests of the hip Virgin Hotel. The lounge has become a popular destination during music festivals like Pitchfork and Lollapalooza with events like sunset-lit DJ sets and lively after-parties.

LH on 22 at London House 

At the top of the swanky London House hotel is a three-level rooftop bar and restaurant with the best view of the Chicago River.

LH on 21 is an indoor restaurant serving New American fare. LH on 22 is the outdoor bar serving craft cocktails. Then there’s the building’s cupola, a sky-high space available for private events and marriage proposals.

Apogee at the Dana Hotel

Want to sip on a jaw-dropping concoction while taking in a jaw-dropping view? Apogee is the place to go for avant garde cocktails, live DJs, fire pits, and incredible panoramic views.

The North River lounge on the 26th floor of the Dana Hotel serves creative craft cocktails with elaborate presentations and whimsical garnishes. Think a glass toadstool, artisanal ice, edible butterflies, and other fun glassware and ceramic vessels perfect for group celebrations.

Oscar Raymundo
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