Are you looking for a luxury hotel in Chicago with a stunning rooftop pool? We know most traveling guests love the option of taking a refreshing dip after a day of exploring. In Chicago, you’ll experience great food, relaxing nature, expansive shops, and a spectacular skyline. So after seeing everything this city has to offer, a nice swim back at the hotel will certainly top off your day. After some research, we have found the best luxury Chicago hotels that offer rooftop pools with great views. We’ll also uncover the best hotels with free breakfasts, bars, and private hot tubs for couples. Check these out!

1. The Penthouse at Grand Plaza

Situated in the heart of downtown Chicago, The Penthouse at Grand Plaza is a spectacular aparthotel. The property offers unobstructed views of the city, spacious apartments, and a luxurious interior. These glamourous penthouses have one or more bedrooms, private balconies, and spacious kitchens. Our favorite unit is Penthouse #1, which is perfect for families, couples, or a group of friends. The unit has two bathrooms, a fireplace, floor-to-ceiling windows, and can accommodate up to eight people. For couples, we recommend booking smaller Penthouse #7, located on the 51st floor. You’ll also find convenient facilities such as a modern fitness center, on-site market, and a basketball court. The main feature at Grand Plaza, of course, is the stunning rooftop pool with a sun deck and breath-taking views of the cityscape.

  • Guest Rating: 9.4
  • Star Rating: 4 stars
  • Address: 540 North State Street, River North, Chicago, IL 60654, United States

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2. Viceroy Chicago

Viceroy Chicago is one of the finest 5-star hotels in the city. It is located a couple of minutes’ walk from Michigan Avenue. The property offers a wide selection of rooms and suites, so you won’t run out of options. Grand Lake View King is a perfect room for tranquillity and comfort seekers. The room has a comfortable bed, panoramic windows, a coffee machine, and a luxurious bathroom with a bathtub. When you’re ready for a swim, the property has a stunning seasonal rooftop pool located on the 18th floor. By the pool, you will find a “Devereaux” rooftop bar that serves signature cocktails and light bites. The hotel also has a state-of-art fitness center and on-site American restaurant “Somerset”.

  • Guest Rating: 9.3
  • Star Rating: 5 stars
  • Address: 1118 North State Street, Chicago, IL 60610, United States

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3. LEVEL Chicago Old Town

LEVEL Chicago Old Town boasts luxurious fully-furnished apartments in the heart of the city. The property combines privacy with resort-like facilities. There are several types of accommodation, ranging from studio to three-bedroom apartments. Each apartment has air conditioning, a full-size kitchen, balconies, and a washing machine. On top of that, guests can enjoy a seasonally heated rooftop pool with a hot tub and comfortable day beds. If you need a workout, head to their modern fitness center, equipped with the best gym equipment along with classes. For those relaxing evenings, the property provides a sun terrace with barbeque facilities.

  • Guest Rating: 9.1
  • Star Rating: 4 stars
  • Address: 1140 North Wells Street, Chicago, IL 60610, United States  

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4. The Robey

Situated on Robey Street, The Robey offers 89 elegant rooms at a central location. The property boasts a selection of well-appointed units, ranging from tower rooms to annex lofts. For couples, we recommend Urban King Tower Room Suite, which showcases views of Lincoln Park and Bucktown. You will also love custom-designed furniture, Calcutta marble countertops, and a spacious bathroom. However, if you love simplicity, select Double Queen Loft Room offering minimal furnishing and a natural interior. On the rooftop, you’ll find a casual triangular pool where guests can enjoy the “Cabana Club” bar. For breakfast, lunch, and dinner, head to the on-site French-American “Café Robey”. For drinks later at night, go to “Up & Up”, a rooftop lounge serving cocktails and spirits with great city views.

  • Guest Rating: 8.9
  • Star Rating: 4 stars
  • Address: 2018 W North Avenue, Wicker Park, Chicago, IL 60647, United States

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5. The Hotel at Midtown

The Hotel at Midtown is a boutique Chicago hotel offering resort-like facilities. 55 unique rooms feature breathtaking views and contemporary design. Whether you are traveling alone or with your partner, the Deluxe King Room offers a relaxing atmosphere. You will love airy design, coffee maker, and panoramic windows. Relax your muscles and enjoy a swim in the outdoor or indoor pool. They both have plenty of space for lap swimming and soothing hot tubs. On top of that, guests can enjoy heartwarming meals and poolside snacks from “Chromium” restaurant. If you fancy a drink, head to the rooftop bar “Six”, offering signature cocktails and Instagram-worthy views.

  • Guest Rating: 8.8
  • Star Rating: 4 stars
  • Address: 2444 North Elston Avenue, Chicago, IL 60647, United States 

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6. The Hoxton, Chicago

Situated in the heart of Fulton Market District, The Hoxton, Chicago offers comfortable rooms and a relaxing environment. The property has 182 rooms, ranging from small to large rooms. Each unit features modern bathrooms, stylish furniture, and floor-to-ceiling windows. Our favorite room is Cosy Up, which provides extra space, an industrial interior, and a spacious walk-in shower. If you have a pet, all rooms are dog-friendly. Guests will also enjoy a relaxing rooftop pool and Peruvian-inspired rooftop “Cabra” restaurant. In the evening, head to the Mediterranean “Cira” restaurant and grab a drink from “Lazy Bird” cocktail bar.

  • Guest Rating: 8.7
  • Star Rating: 4 stars
  • Address: 200 North Green Street, West Loop, Chicago, IL 60607, United States

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7. Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago is situated within walking distance from Magnificent Mile and Granta Park. All 334 rooms and suites provide great city views, modern appliances, and comfortable furniture. King Bed with Balcony is a perfect choice for couples. This room has a luxury bathroom and a private balcony. For active travelers, the hotel features indoor and outdoor pools, a modern fitness center, and an outdoor terrace. The outdoor rooftop pool is a great place to relax, swim some laps, and enjoy the sun. For food and drinks, the contemporary “FireLake Grill House & Cocktail Bar” offers Midwestern dishes and signature cocktails. 

  • Guest Rating: 8.5
  • Star Rating: 4 stars
  • Address: 221 North Columbus Drive, Chicago Loop, Chicago, IL 60601, United States

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8. DoubleTree by Hilton Chicago Magnificent Mile

DoubleTree by Hilton Chicago Magnificent Mile is just a couple of minutes’ walk from Navy Pier and Magnificent Mile. The hotel has a wide selection of rooms, suites, and accessible rooms. If you are visiting Chicago for a romantic getaway, we suggest booking the Deluxe One Bedroom Suite. The suite offers complimentary coffee, a minibar, two TVs, and a dining table. You can also take advantage of the well-equipped fitness center and seasonal rooftop pool. If you get the munchies, there is an on-site “HotHouse” restaurant, serving international and American cuisine and drinks. For people who are always in a rush, the property offers a “Made Market” counter with salads, sandwiches, and juices.

  • Guest Rating: 8.4
  • Star Rating: 4 stars
  • Address: 300 East Ohio Street, Streeterville, Chicago, IL 60611, United States

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9. Homewood Suites Chicago Downtown – Magnificent Mile

Homewood Suites Chicago Downtown is close to the Museum of Contemporary Art and steps away from Magnificent Mile. The property is well-known for its exceptional breakfast, free Wi-Fi, and airy design. The Lake View Suite offers a separate living room, full kitchen, and sofa bed. It can accommodate up to four people, too. Furthermore, here guests will find an intimate fitness center and relaxing rooftop pool. Everyone will be able to enjoy the spectacular Chicago’s skyline while lounging by the pool. The property also offers pet-friendly suites.

  • Guest Rating: 8.3
  • Star Rating: 3 stars
  • Address: 125 West Ohio Street, River North, Chicago, IL 60610, United States

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10. Holiday Inn Hotel & Suites Chicago – Downtown

Holiday Inn Hotel & Suites Chicago – Downtown offers a convenient location while exploring the city. The hotel is within walking distance from Old Post Office, Willis Tower, and Chicago Loop. There is a wide selection of rooms suitable for various budgets. Each unit offers complimentary Wi-Fi, a comfortable bed, and a modern bathroom. To cool down after a day of exploring, you can relax by the outdoor swimming pool which is surrounded by city views. On-site “Sunny’s Restaurant” is open for breakfast, lunch, and dinner. Here you can enjoy American dishes, including starters and desserts. There is also an evening cocktail lounge that serves specialty cocktails and spirits.

  • Guest Rating: 7.6
  • Star Rating: 3 stars
  • Address: 506 West Harrison, Chicago, IL 60607, United States 

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Chicago Rooftop Pool Hotels Map

Also read:

Find More Chicago Hotels with Pools


What’s the best luxury Chicago hotel with a rooftop pool and bar?

Viceroy Chicago is definitely the best hotel with a rooftop pool and bar.

While the rooftop pool is seasonal, you can still enjoy stunning views of the city from the 18th floor at “Devereaux” bar.

This bar is well-known for its specialty cocktails.

We recommend trying Golden Ratio, Voodoo Boogie, or En Maison.

For food lovers, we recommend The Hoxton, Chicago’s “Cabra” rooftop restaurant offering Peruvian-inspired meals and shared plates.

What’s the best luxury Chicago hotel with a rooftop pool and whirlpool hot tub?

The Hotel at Midtown has 2 pools both with heated whirlpool hot tubs for guests to relax.

The outdoor rooftop pool is open Monday to Saturday 5am-10pm.

While the indoor pool is open daily from 5am-10pm.

What’s the best luxury Chicago hotel with a rooftop pool and free breakfast?

Homewood Suites Chicago Downtown – Magnificent Mile offers daily complimentary breakfasts for adults and kids.

The breakfast includes a wide selection of hot and cold food, drinks, and sweet treats.

You will find plenty of choices for kids, too.

What’s the best luxury Chicago hotel with a rooftop pool for couples?

We recommend The Penthouse at Grand Plaza for couples who enjoy intimacy, tranquillity, and luxury.

This aparthotel has spacious serviced apartments with private balconies and spectacular views of the Chicago skyline.

It also offers an all-year-round rooftop swimming pool, perfect for lounging and enjoying a romantic night view.

What’s the best luxury Chicago hotel with a rooftop pool for families with kids?

LEVEL Chicago Old Town offers stunning family-friendly apartments for an attractive price.

It has a large seasonal swimming pool, basketball court, and games room with a ping pong table and arcades.

The property is also near Lincoln Park Zoo, making it a perfect place for a day out.


Chicago Rooftop Pool HotelsRatings
The Penthouse at Grand Plaza9.4
Viceroy Chicago9.3
LEVEL Chicago Old Town9.1
The Robey8.9
The Hotel at Midtown8.8
The Hoxton, Chicago8.7
Radisson Blu Aqua Hotel Chicago8.5
DoubleTree by Hilton Chicago Magnificent Mile8.4
Homewood Suites Chicago Downtown – Magnificent Mile8.3
Holiday Inn Hotel & Suites Chicago – Downtown7.6

For all new cities, I go overboard on my itinerary, just to see every major attraction. Countries I've visited include New Zealand, Singapore, Hong Kong, China, Cambodia, Japan and Thailand. Mostly Asian countries. Next target - Europe!