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

Indoor pool, open 5:00 AM to 11:00 PM, sun loungers
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3460)
"Amazing stay, beautiful view!"
United States
Joshua
The price is ￥16,422
￥19,278 total
includes taxes & fees
Dec 14 - Dec 15
voco Chicago Downtown - Riverwalk by IHG
Indoor pool, open 7:00 AM to 10:00 PM, sun loungers
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2956)
"Great location and great staff!!"
United States
lynne
The price is ￥12,621
￥14,816 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Aloft Chicago Mag Mile
Indoor pool
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1049)
"Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food."
United States
Hannah
The price is ￥15,238
￥22,452 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hyatt Centric Chicago Magnificent Mile
Pool
Hilton Garden Inn Chicago Downtown South Loop

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, (1756)
"Clean and staff was courteous. "
United States
HANNAH
The price is ￥11,094
￥13,021 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hilton Garden Inn Chicago Downtown South Loop
Indoor pool
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

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, (2742)
"Clean room and friendly staff, overall good stay "
United States
eesaa saalik
The price is ￥12,340
￥19,059 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Indoor pool
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2312)
"Wonderful customer service, great location! "
United States
Michelle
The price is ￥15,533
￥23,212 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Royal Sonesta Chicago River North
Indoor pool
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2126)
"Loved and enjoyed our stay"
United States
Luis
The price is ￥17,213
￥24,093 total
includes taxes & fees
Dec 29 - Dec 30
Palmer House a Hilton Hotel
Outdoor pool, cabanas (surcharge), pool umbrellas
DoubleTree by Hilton 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, (2185)
"The staff was amazing , can’t wait to return "
United States
Jasmin
The price is ￥13,898
￥16,315 total
includes taxes & fees
Jan 7 - Jan 8, 2026
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool
Holiday Inn Chicago Dwtn - The Mart by IHG

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, (2034)
"room was good,location was perfect!"
United States
Kyan
The price is ￥16,204
￥19,022 total
includes taxes & fees
Dec 23 - Dec 24
Holiday Inn Chicago Dwtn - The Mart by IHG
Indoor pool
The Wade

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1513)
"Everything was really wonderful.. would stay again for sure!! "
United States
Alexa
The price is ￥15,704
￥18,436 total
includes taxes & fees
Dec 17 - Dec 18
The Wade
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.
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Top Westchester Hotel Reviews

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"Always dependable for a comfortable stay. "
jennifer 3-night trip
Posted 14 hours ago
Palmer House a Hilton Hotel

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Frequently asked questions

What are some accommodations with pools in Westchester?
Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from Michigan Avenue. Features full, 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. Silversmith Hotel Chicago Downtown: Hotel, 2-minute walk from State Street. Features a snack bar/deli, a pool, and buffet. Palmer House a Hilton Hotel: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool, and a health club. Eurostars Magnificent Mile: Hotel steps from Michigan Avenue. Features 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 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.