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Top 10 Hotels With A Rooftop Pool In Chicago, Illinois

Chia Han Keong
Updated Aug 30, 2018

“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 sumptuous dining options, waiting for you to explore and savor. Better still, book a hotel with a rooftop pool, such as these 10 accommodation choices, and you can take in the soaring skyline at your own leisure.

1. Viceroy Chicago (from 245 USD)

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 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, the hotel is an excellent base for your Chicago explorations.

Viceroy Chicago

Address: 1118 North State Street, Chicago, IL 60610, USA (see map)

Price: from 245 USD

Star Rating: 5 Star

Travelers Review: Exceptional 9.5 (from 176 reviews)

See our full list of recommended Hotels in Chicago and also compare the prices with Vacation Rentals in Chicago

2. The Hotel at Midtown (from 229 USD)

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 indoor and outdoor lap pools, gym classes, massage treatments, yoga studios, tennis courts, and even golf simulators. 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 sports entertainment, Chicago’s beloved baseball team, the Cubs, play at the iconic Wrigley Field just a 10-minute drive away.

The Hotel at Midtown

Address: 2444 North Elston Avenue, Chicago, IL 60647, USA (see map)

Price: from 229 USD

Star Rating: 4 Star

Travelers Review: Very Good 8.5 (from 31 reviews)

See our full list of recommended Hotels in Chicago and also compare the prices with Vacation Rentals in Chicago

3. The Penthouse at Grand Plaza (from 942 USD)

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. Guests can also unwind at the rooftop swimming pool and the sun deck, or make use of the fitness center and the basketball court on the premises. There are great dining options all around the Plaza, and the Navy Pier with all its children’s attractions and entertainment is just a 10-minute walk away.

The Penthouse at Grand Plaza

Address: 540 North State Street, River North, Chicago, IL 60654, USA (see map)

Price: from 942 USD

Star Rating: 4 Star

Travelers Review: Superb 9.2 (from 93 reviews)

See our full list of recommended Hotels in Chicago and also compare the prices with Vacation Rentals in Chicago

4. Radisson Blu Aqua Hotel Chicago (from 266 USD)

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 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 by the outdoor rooftop pool, which comes with fire pits and a sun deck.

Radisson Blu Aqua Hotel Chicago

Address: 221 North Columbus Drive, Chicago Loop, Chicago, IL 60601, USA (see map)

Price: from 266 USD

Star Rating: 4 Star

Travelers Review: Fabulous 8.9 (from 1,323 reviews)

See our full list of recommended Hotels in Chicago and also compare the prices with Vacation Rentals in Chicago

5. The Robey (from 240 USD)

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 hotel 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, Wicker Park, Chicago, IL 60647, USA (see map)

Price: from 240 USD

Star Rating: 4 Star

Travelers Review: Superb 9.1 (from 196 reviews)

See our full list of recommended Hotels in Chicago and also compare the prices with Vacation Rentals in Chicago

6. Hampton Inn Chicago Downtown/Magnificent Mile (from 158 USD)

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 centers. 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, which has spacious guestrooms with plush beds for you to unwind. Even better is its rooftop pool, 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, Streeterville, Chicago, IL 60611, USA (see map)

Price: from 158 USD

Star Rating: 3 Star

Travelers Review: Fabulous 8.7 (from 622 reviews)

See our full list of recommended Hotels in Chicago and also compare the prices with Vacation Rentals in Chicago

7. DoubleTree by Hilton Chicago Magnificent Mile (from 147 USD)

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 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, Streeterville, Chicago, IL 60611, USA (see map)

Price: from 147 USD

Star Rating: 3 Star

Travelers Review: Very Good 8.2 (from 2,076 reviews)

See our full list of recommended Hotels in Chicago and also compare the prices with Vacation Rentals in Chicago

8. Homewood Suites Chicago Downtown/Magnificent Mile (from 152 USD)

Traveling families will not be short of kid-friendly attractions in Chicago. 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, which offers spacious suites with full kitchens for the perfect family stay. With a seasonal rooftop pool 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, Streeterville, Chicago, IL 60611, USA (see map)

Price: from 152 USD

Star Rating: 3 Star

Travelers Review: Fabulous 8.9 (from 334 reviews)

See our full list of recommended Hotels in Chicago and also compare the prices with Vacation Rentals in Chicago

9. Holiday Inn Hotel & Suites Chicago Downtown (from 126 USD)

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, Chicago, IL 60607, USA (see map)

Price: from 126 USD

Star Rating: 3 Star

Travelers Review: Good 7.9 (from 253 reviews)

See our full list of recommended Hotels in Chicago and also compare the prices with Vacation Rentals in Chicago

10. Hilton Chicago/Magnificent Mile Suites (from 167 USD)

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, Streeterville, Chicago, IL 60611-1719, USA (see map)

Price: from 167 USD

Star Rating: 4 Star

Travelers Review: Fabulous 8.6 (from 967 reviews)

See our full list of recommended Hotels in Chicago and also compare the prices with Vacation Rentals in Chicago

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 hotel in Chicago right away, and preferably one with a great view of the awesome, skyscraper-filled skyline.

This article was originally published on May 17, 2018

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

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