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

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Our top choices for Westchester hotels with a pool

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,470 reviews)
The price is AED 567
AED 674 total
includes taxes & fees
5 Jul - 6 Jul
Hilton Chicago/Magnificent Mile Suites

The Wade

The Wade
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,869 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 AED 621
AED 738 total
includes taxes & fees
1 Jul - 2 Jul
The Wade

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,105 reviews)
  • cleanliness
    Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, hot tub haven, and 24-hour fitness center.
The price is AED 724
AED 970 total
includes taxes & fees
30 Jun - 1 Jul
Hyatt Centric Chicago Magnificent Mile

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,689 reviews)
  • cleanliness
    Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.
The price is AED 804
AED 1,087 total
includes taxes & fees
5 Jul - 6 Jul
Sheraton Grand Chicago Riverwalk

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,931 reviews)
The price is AED 606
AED 721 total
includes taxes & fees
6 Jul - 7 Jul
Courtyard by Marriott Chicago Magnificent Mile

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,301 reviews)
  • cleanliness
    Splash into the city at this downtown hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.
The price is AED 547
AED 651 total
includes taxes & fees
2 Jul - 3 Jul
Aloft by Marriott Chicago Mag Mile

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 AED 878
AED 1,152 total
includes taxes & fees
1 Jul - 2 Jul
The Hoxton, Chicago

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,956 reviews)
  • cleanliness
    Luxurious indoor and seasonal outdoor pools form a relaxing oasis near Millennium Park and Michigan Avenue.
The price is AED 834
AED 1,105 total
includes taxes & fees
6 Jul - 7 Jul
Radisson Blu Aqua Hotel Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (2,879 reviews)
  • cleanliness
    Chicago hotel offers refreshing stays with indoor pool, fitness center, and walkable Michigan Avenue access.
The price is AED 629
AED 856 total
includes taxes & fees
5 Jul - 6 Jul
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

JW Marriott Chicago

JW Marriott Chicago
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Sleek indoor pool sanctuary opens onto Chicago adventures in this luxury retreat.
The price is AED 878
AED 1,175 total
includes taxes & fees
2 Jul - 3 Jul
JW Marriott Chicago
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.

Choose what matters most at hotels with a pool in Westchester

Top Westchester Hotel Reviews

Frequently asked questions

What are some accommodations 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 center. 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 like 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're planning to visit Westchester in the hottest months of July, August, or June when the average temp is 71°F. Lodging 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 31°F.