A calm lake with ducks, autumn trees, and a grassy park area.

Hotels with Swimming Pools in Westchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Westchester Hotels with Swimming Pools

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul

Our top choices for Westchester hotels with a pool

Indoor pool

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,475 reviews)
The price is S$249
includes taxes & fees
7 Jul - 8 Jul
Hilton Chicago/Magnificent Mile Suites
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,876 reviews)
  • cleanliness
    Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.
The price is S$260
includes taxes & fees
1 Jul - 2 Jul
The Wade
Indoor pool

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,107 reviews)
  • cleanliness
    Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, hot tub haven, and 24-hour fitness centre.
The price is S$342
includes taxes & fees
30 Jun - 1 Jul
Hyatt Centric Chicago Magnificent Mile
Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,304 reviews)
  • cleanliness
    Splash into the city at this city centre hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.
The price is S$229
includes taxes & fees
2 Jul - 3 Jul
Aloft by Marriott Chicago Mag Mile
Indoor pool

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,933 reviews)
The price is S$254
includes taxes & fees
6 Jul - 7 Jul
Courtyard by Marriott Chicago Magnificent Mile
Seasonal outdoor pool

The Hoxton, Chicago

The Hoxton, Chicago
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.
The price is S$406
includes taxes & fees
1 Jul - 2 Jul
The Hoxton, Chicago
Fitness facility

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,691 reviews)
  • cleanliness
    Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.
The price is S$383
includes taxes & fees
5 Jul - 6 Jul
Sheraton Grand Chicago Riverwalk
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,521 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is S$264
includes taxes & fees
5 Jul - 6 Jul
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,958 reviews)
  • cleanliness
    Luxurious indoor and seasonal outdoor pools form a relaxing oasis near Millennium Park and Michigan Avenue.
The price is S$389
includes taxes & fees
6 Jul - 7 Jul
Radisson Blu Aqua Hotel Chicago
Indoor pool

Best Western River North Hotel

Best Western River North Hotel
2.5 star property
Downtown Chicago
7.8 out of 10, Good, (1,141 reviews)
  • cleanliness
    Splash into year-round pool fun at this Michigan Avenue hotel with a modern fitness centre.
The price is S$208
includes taxes & fees
1 Jul - 2 Jul
Best Western River North Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Westchester

Breakfast included
Hot tub

Top Westchester Hotel Reviews

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

8/10 Good
"Very close to airport"
Mahmood 1-night trip
Posted less than an hour ago
Hilton Chicago O'Hare Airport

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. Hilton Chicago/Magnificent Mile Suites: Hotel steps from State Street. Features a full-service spa, an indoor pool and a 24-hour fitness centre. The Chicago Hotel Collection - Magnificent Mile: Hotel steps from Michigan Avenue. Provides 2 restaurants, an indoor pool and a sauna.
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.

Explore a world of travel with Expedia