Find Hotels with a Pool in Westchester, IL

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Check availability on Westchester Hotels with a Pool

Our top choices for Westchester hotels with a pool

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2949)
"Great location and great staff!!"
United States
lynne
The price is NT$2,401
NT$2,819 total
includes taxes & fees
Dec 15 - Dec 16
Aloft Chicago Mag Mile

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1748)
"Clean and staff was courteous. "
United States
HANNAH
The price is NT$2,220
NT$2,606 total
includes taxes & fees
Jan 7 - 2026/1/8
Hilton Garden Inn Chicago Downtown South Loop

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3454)
"Great value and location"
United States
Kelly
The price is NT$3,492
NT$4,100 total
includes taxes & fees
Dec 29 - Dec 30
voco Chicago Downtown - Riverwalk by IHG

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1045)
"Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food."
United States
Hannah
The price is NT$3,048
NT$4,493 total
includes taxes & fees
Jan 4 - 2026/1/5
Hyatt Centric Chicago Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2180)
"Nice Hotel"
United States
Alan
The price is NT$2,787
NT$3,272 total
includes taxes & fees
Dec 23 - Dec 24
DoubleTree by Hilton Chicago - Magnificent Mile

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2133)
"Loved and enjoyed our stay"
United States
Luis
The price is NT$3,452
NT$4,832 total
includes taxes & fees
Dec 23 - Dec 24
Palmer House a Hilton Hotel

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, (2752)
"Great food clean room friendly staff"
United States
MARINA
The price is NT$2,544
NT$3,902 total
includes taxes & fees
Jan 11 - 2026/1/12
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (4233)
"Clean room, very friendly staff and great location "
United States
Marcia
The price is NT$2,620
NT$3,076 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2033)
"room was good,location was perfect!"
United States
Kyan
The price is NT$3,056
NT$3,587 total
includes taxes & fees
Dec 24 - Dec 25
Holiday Inn Chicago Dwtn - The Mart by IHG

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2128)
"Very nice place"
United States
Salman
The price is NT$2,470
NT$2,899 total
includes taxes & fees
Jan 6 - 2026/1/7
Homewood Suites by Hilton Chicago Downtown South Loop
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.

Top Westchester Hotel Reviews

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Frequently asked questions

What are some accommodations with pools in Westchester?
Palmer House a Hilton Hotel: Hotel steps from State Street. Features a full-service spa, an indoor pool, and a 24-hour fitness center. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool, and flat-screen televisions. Hilton Chicago/Magnificent Mile Suites: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel: Hotel, 4-minute walk from State Street. Features 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 like Wrigley Field, Michigan Avenue, and United Center. 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.