The 11 Best Hotels With Rooftop Pools in Chicago, Illinois, USA

hotels with rooftop pool in chicago
Chia Han Keong
Chia Han Keong

“Hollywood is hype, New York is talk, Chicago is work,” so said the actor Michael Douglas. Indeed, Chicago epitomizes the no-nonsense heart and soul of Middle America, proof that grit and strength can build skyscrapers to withstand the harsh winds of the Windy City. The third biggest city in the United States, Chicago has arguably the finest-looking downtown skyline in the country, set beside the picturesque shores of Lake Michigan. And amid all those tall buildings are world-class museums, huge parks, spectacular entertainment, and amazing dining options, waiting for you to explore and savor. Better still, book one of the best hotels with rooftop pools in Chicago, so you can take in the soaring skyline at your own leisure.

1. Viceroy Chicago (from USD 148)

With its iconic elevated rail snaking along hundreds of towering skyscrapers, the dense urban jungle of downtown Chicago exudes an awe-inspiring bustle for first-time visitors. Whether you are embarking on a shopping spree along with the bevy of shops along Magnificent Mile, or simply admiring the public art and architecture all around, you cannot help but be astonished at the massive sprawl of this city. If you choose the Viceroy Chicago as your choice of accommodation, you will be able to enjoy sweeping panoramas of the city center right up at its 18th-floor rooftop pool and lounge. Just a five-minute walk from the Magnificent Mile shopping district and 10 minutes from the lakefront, this stellar property is one of the ideal hotels in Chicago with a rooftop pool and bar to stay in for those who want an ideal staycation when in a vacation.

Viceroy Chicago

Address: 1118 North State Street
Price: from 148 USD

Fire extinguishers Property is cleaned by professional cleaning companies Cashless payment available Dry cleaning Bar Heating Staff follow all safety protocols as directed by local authorities Lift

2. The Hotel at Midtown (from USD 143)

Imagine a hotel built on the premises of Chicago’s renowned Midtown Athletic Club. Guests will be able to enjoy all the club’s fitness and spa facilities, including an indoor pool, gym classes, massage treatments, yoga studios, tennis courts, and even golf simulators. It’s also a Chicago hotel with an outdoor pool. This is the exciting concept of The Hotel at Midtown, a boutique hotel for health-minded travelers. Even its on-site restaurants serve classic American fare crafted with natural, energizing foods to treat the body and mind right. And if you are eager for more shopping, sports entertainment, Chicago’s beloved baseball team, the Cubs, play at the iconic Wrigley Field just a 10-minute drive away, as well as other popular malls and shops for those keen on finding the best souvenirs.

The Hotel at Midtown

Address: 2444 North Elston Avenue
Price: from 143 USD

WiFi Vending machine (drinks) WiFi available in all areas Shops (on site) Barber/beauty shop CCTV in common areas Express check-in/check-out Thermometers for guests provided by property

3. The Penthouse at Grand Plaza (from USD 309)

If you desire a luxurious accommodation right in the heart of Chicago, look no further than these spacious penthouse units atop Grand Plaza just north of the Chicago River in downtown. Enjoy unparalleled views of the city through the floor-to-ceiling windows while relaxing on the cozy sofas and beds in the spacious units. All units have fully-equipped kitchens, laundry facilities, and three separate balconies.

It’s also one of the hotels in Chicago with a rooftop pool and a sun deck, where guests can unwind. It also has a fitness center and a basketball court on the premises. There are great dining options all around the Plaza, and the Navy Pier, one of the city’s best tourist attractions and sources of entertainment for kids, is just a 10-minute walk away. Indeed, The Penthouse is one of the best hotels with rooftop pools in Chicago that has a prime location, superb amenities, and high-quality rooms for every travelers’ convenience and comfort.

The Penthouse at Grand Plaza

Address: 540 North State Street
Price: from 309 USD

Rooftop pool Air conditioning Lift Outdoor pool Heating Fence around pool Internet services Mini-market on site

4. Radisson Blu Aqua Hotel Chicago (from USD 109)

Lest you think downtown Chicago is nothing but a concrete jungle, it dazzles you with two huge lakeside parks, the Grant Park and the Millennium Park, that rival New York’s Central Park for being an oasis amid the dense urban bustle. Check out Grant Park’s pretty Buckingham Fountain as well as Millennium Park’s numerous modern sculptures, but do not miss the magnificent Art Institute of Chicago House housed right in the middle of the parks. The Radisson Blu Aqua Hotel Chicago is just a stone’s throw away from these attractions, and it, too, has a manicured lifestyle garden within its premises. Guests can also enjoy the downtown vistas as this hotel has one of the best outdoor rooftop pools Chicago has to offer, which comes with fire pits and a sun deck.

Radisson Blu Aqua Hotel Chicago

Address: 221 North Columbus Drive
Price: from 109 USD

Security alarm Fence around pool Shoeshine Games room Family rooms Pool bar Non-smoking rooms Fire extinguishers

5. The Robey (from USD 104)

All the great cities in the world have one thing in common: they have suburban neighborhoods filled with idiosyncratic character and atmosphere. Chicago, for example, has Wicker Park, an ultra-cool enclave with a fertile music scene that has seen the likes of Smashing Pumpkins and Liz Phair make their names early in their respective careers. Art studios and annual visual arts festivals still abound, so if you want to explore this suburb in earnest, you can base yourself at The Robey, a chic Chicago hotel with a rooftop pool. It’s housed in the only skyscraper in this neighborhood, the Art Deco-styled Northwest Tower. Whether you are relaxing at the outdoor pool or indoor lounge at the rooftop, you are bound to enjoy the unblocked vistas of this massive city as well as the charms of this quaint neighborhood.

The Robey

Address: 2018 W North Avenue
Price: from 104 USD

Safety deposit box WiFi Shared stationery such as printed menus, magazines, pens, and paper removed 24-hour front desk Invoice provided Massage Happy hour Internet services

6. Hampton Inn Chicago Downtown/Magnificent Mile (from USD 81)

Shopaholics will absolutely adore the Magnificent Mile, a stretch of North Michigan Avenue which is dotted with world-famous retail stores, luxury boutiques, and massive shopping mall. Shop till you drop? Not if you have a comfortable accommodation right along this shopping strip to rest your tired legs in. Try the Hampton Inn Chicago Downtown/Magnificent Mile, one of the hotels in downtown Chicago which has a spacious guestroom with plush beds for you to unwind. It also has one of the best hotel pools in Chicago, perched high above on the 40th floor, offering spectacular views all the way to Lake Michigan. Undoubtedly a great resting place after your shopping exertions.

Hampton Inn Chicago Downtown/Magnificent Mile

Address: 160 East Huron Street
Price: from 81 USD

Screens or physical barriers placed between staff and guests in appropriate areas Hand sanitizer in guest accommodation and key areas Tour or class about local culture Staff follow all safety protocols as directed by local authorities Temporary art galleries Safety deposit box 24-hour front desk Stand-up comedy

7. DoubleTree by Hilton Chicago Magnificent Mile (from USD 137)

Believe it or not, there are sandy beaches in downtown Chicago along Lake Michigan where you can enjoy some sun-tanning and swimming. Check out Oak Street Beach or Ohio Street Beach if you want some beach action. Better still, head north to Lincoln Park, an expansive parkland that houses the famous Lincoln Park Zoo and the Chicago History Museum. The park lies right beside the huge North Avenue Beach, a great place for people-watching and serious beach volleyball action. The DoubleTree by Hilton Chicago Magnificent Mile hotel lies between the beachfront and the shopping district, giving you excellent convenience should you wish to see both sides of the Windy City. You will enjoy contemporary comfort amid the stylish guestrooms, while the rooftop pool and on-site restaurants are great options to unwind and recharge.

DoubleTree by Hilton Chicago Magnificent Mile

Address: 300 East Ohio Street
Price: from 137 USD

Contactless check-in/check-out Internet services Physical distancing in dining areas Fitness centre Paid WiFi Lift Family rooms Delivered food is securely covered

8. Homewood Suites Chicago Downtown/Magnificent Mile (from USD 94)

Traveling families will not be short of kid-friendly attractions in Chicago. There are a lot of things to do in downtown Chicago, and you’ll never get bored. Head to the lakefront to check out the Shedd Aquarium, the Adler Planetarium, and the Field Museum which houses the world’s largest Tyrannosaurus Rex skeleton. Or head to the top of Willis Tower, the second tallest building in the United States, for some vertigo-inducing views of the city. Or simply treat your kids to an excellent deep-dish pizza or hot dogs, all done in Chicago’s inimitable style. Families can also find great accommodation at the Homewood Suites Chicago Downtown/Magnificent Mile. It is another Chicago hotel with a rooftop pool that offers spacious suites with full kitchens for the perfect family stay. With its seasonal rooftop pool area affording great city views and on-site restaurants with an outdoor patio, this is a fantastic base to see most of the city attractions.

Homewood Suites Chicago Downtown - Magnificent Mile

Address: 152 East Huron Street
Price: from 94 USD

WiFi ATM/cash machine on site Free WiFi Linens, towels and laundry washed in accordance with local authority guidelines Guest accommodation sealed after cleaning Safety deposit box Access to health care professionals Staff follow all safety protocols as directed by local authorities

9. Holiday Inn Hotel & Suites Chicago Downtown (from USD 79)

Chicago’s Near West Side district is an excellent area to explore, with a jumble of neighborhoods each exuding unique flavor. Check out Little Italy and Greektown for great food and tourist-friendly charm. Or head to the West Loop, which features the city’s top restaurants, a thriving gallery scene, and several hot nightclubs. Sports nuts can head to the United Center, home of the Chicago Bulls and the old stomping ground of the legendary Michael Jordan. A great hotel to stay in would be the Holiday Inn Hotel and Suites Chicago Downtown, which features clean guestrooms and an outdoor pool with fitness facilities.

Holiday Inn Hotel & Suites Chicago - Downtown

Address: 506 West Harrison
Price: from 79 USD

Shared lounge/TV area Breakfast takeaway containers Outdoor pool (seasonal) Laundry Physical distancing in dining areas Luggage storage Guest accommodation is disinfected between stays Vending machine (drinks)

10. Hilton Chicago/Magnificent Mile Suites (from USD 111)

The Hilton Chicago/Magnificent Mile Suites is a classy all-suites hotel, ideal for families with kids, situated a block away from the Magnificent Mile shopping strip. Each suite offers separate living and sleeping spaces, 42-inch HDTVs, and unique Chicago-themed touches. Enjoy great views from the indoor rooftop pool and the fitness center, or step out to visit the nearby lakefront or the striking Museum of Contemporary Art Chicago, which always has some interesting exhibitions.

Hilton Chicago/Magnificent Mile Suites

Address: 198 East Delaware Place
Price: from 111 USD

First aid kit available Concierge service Pets allowed All plates, cutlery, glasses and other tableware have been sanitized Lift Air conditioning Safety deposit box Fitness centre

11. Best Western River North Hotel (from USD 72)

Best Western River North Hotel is located in the prime area of downtown Chicago and is just five blocks away from the Magnificent Mile, where you can dine and shop to your heart’s content. The hotel’s front desk, gym, and business center are all open 24 hours. Pizzeria Ora Restaurant and Lounge is perfect for those who want a taste of Chicago’s famous deep-dish pizza, with in-room dining service available upon request. It has a rooftop pool and deck that offers a great view of the Chicago skyline. The hotel is just a 35-minute drive from the airport, and you also have local attractions such as Navy Pier and Millenium Park just 2.4 km (1.4 mi) away, while Wrigley Field is 9.6 km (5.9 mi) away.

Best Western River North Hotel

Address: 125 West Ohio Street
Price: from 72 USD

Smoke alarms Indoor pool Lift Physical distancing in dining areas Luggage storage Business centre Fax/photocopying Pool/beach towels

Charms amid massive urban sprawl

If anything, Chicago is slightly underrated as a great American city, with most of the limelight taken by New York or Los Angeles or even Boston. But this Midwestern juggernaut offers so many charms that you can easily spend weeks amid its massive sprawl. So book yourself a room in a Chicago hotel with a rooftop pool, and preferably one with a great view of the awesome, skyscraper-filled skyline. Whatever type of accommodations you prefer, from boutique hotels in Chicago to luxury five-star hotels, there’s definitely something for every type of traveler making their way to this part of Illinois.

Frequently asked questions about the best hotels with rooftop pools in Chicago

1. Which are the best hotels in Chicago with a rooftop pool?

Some of the highly recommended hotels with a rooftop pool in Chicago include the Robey with a separate indoor pool and DoubleTree by Hilton which offers a beachfront view near the shopping district.

2. Which hotels in Chicago with a rooftop pool are good for families?

The Homewood Suites Chicago Downtown/Magnificent Mile and Hilton Chicago/Magnificent Mile Suites are two of the best suggestions for families who wish to stay somewhere with great amenities, like a rooftop pool, when traveling to Chicago.

3. Which are the best hotels with rooftop pools and balconies in Chicago?

The Penthouse at Grand Plaza is the best hotel we suggest for guests to stay at, complete with a rooftop pool, and a balcony for guests to enjoy when visiting the lovely town of Chicago.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Han Keong is a former sports journalist in Singapore whose lifelong passions are travel and music.

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