TOP Hotels with Swimming Pool in Westchester, IL for 2026

Q: What are some accommodation options with pools in Westchester?

Congress Plaza Hotel : Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. The Chicago Hotel Collection - Magnificent Mile : Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool and flat-screen televisions. Hotel Riu Plaza Chicago : Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool and a sauna. Freehand Chicago : Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool and a sauna. Hyatt Regency O'Hare Chicago : Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool and a health club.

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Our top choices for Westchester hotels with a pool

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

₹18,231 total

includes taxes & fees

7 Jul - 8 Jul

Sheraton Grand Chicago Riverwalk

Downtown Chicago

Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.

₹29,939 total

includes taxes & fees

6 Jul - 7 Jul

Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.

₹22,356 total

includes taxes & fees

7 Jul - 8 Jul

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Dive into city centre luxury with a rejuvenating pool experience close to Chicago landmarks.

₹17,635 total

includes taxes & fees

5 Jul - 6 Jul

Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Splash into the city at this city centre hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.

₹19,003 total

includes taxes & fees

6 Jul - 7 Jul

Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers

Radisson Blu Aqua Hotel Chicago

Downtown Chicago

Luxurious indoor and seasonal outdoor pools form a relaxing oasis near Millennium Park and Michigan Avenue.

₹26,675 total

includes taxes & fees

1 Jul - 2 Jul

The Wade

Downtown Chicago

Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.

₹22,189 total

includes taxes & fees

2 Jul - 3 Jul

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

World-class indoor pool in city centre offers lap swimming and family fun at this luxury hotel.

₹25,541 total

includes taxes & fees

1 Jul - 2 Jul

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Choose what matters most at hotels with a pool in Westchester

Breakfast included

Hot tub

Top Westchester Hotel Reviews

Fairmont Chicago at Millennium Park

8/10 Good

"Clean room, overall nice hotel, restaurant was nice for happy hour. Lobby smelled like an old lady and peltons in gym were broken. Overall lovely stay."

Hotel Felix River North/Magnificent Mile

8/10 Good

"Hotel Felix was in a fantastic location. The staff were very friendly. Our room on the 9th floor with 2 double beds was small, with only a mini fridge. The curtains were old and difficult to open and close. The WiFi would drop or was very slow. The television also provided issues, turning off or to the starting screen, multiple times. The hotel offered only coffee/tea and fresh fruit until 9am. The staff made our stay more enjoyable."

Frequently asked questions

What are some accommodation options with pools in Westchester?

Congress Plaza Hotel: Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. The Chicago Hotel Collection - Magnificent Mile: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool and flat-screen televisions. Hotel Riu Plaza Chicago: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool and a sauna. Freehand Chicago: Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool and a sauna. Hyatt Regency O'Hare Chicago: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool and a health club.

What is there to see and do in Westchester?

While you're in the area, consider exploring places such as Wrigley Field, Michigan Avenue and Soldier Field. Take a walk along the waterfront at Oak Street Beach and North Avenue Beach. The restaurants and shopping are just some of the things to enjoy while you're in the area.

When is the best time to book a hotel with a pool in Westchester?

You may want to consider a place to stay that has an outdoor pool if you plan to visit Westchester in the hottest months of July, August or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is -1°C.

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