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

Outdoor 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, (2,236 reviews)
"Great hotel "
United States
Jeffrey
The price is NT$2,698
NT$3,167 total
includes taxes & fees
Feb 1 - Feb 2
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool, open 7:00 AM to 10:00 PM, sun loungers

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,032 reviews)
"All around a nice stay for the holiday "
United States
Alec
The price is NT$2,497
NT$2,932 total
includes taxes & fees
Jan 29 - Jan 30
Aloft Chicago Mag Mile
Indoor pool

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,066 reviews)
"Amazing location, excellent service and great pool and hot tub. "
United States
Tim
The price is NT$3,098
NT$4,565 total
includes taxes & fees
Jan 25 - Jan 26
Hyatt Centric Chicago Magnificent 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, (1,671 reviews)
"Would definitely stay again…location was perfect "
United States
Ashley
The price is NT$3,202
NT$3,759 total
includes taxes & fees
Feb 5 - Feb 6
Courtyard by Marriott Chicago Magnificent Mile
Indoor pool, open 5:00 AM to 11:00 PM, sun loungers

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3,597 reviews)
"Great location and breakfast.. can be a bit pricey but worth it. "
Canada
Shaurya
The price is NT$3,670
NT$4,308 total
includes taxes & fees
Feb 15 - Feb 16
voco Chicago Downtown - Riverwalk by IHG
Pool

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, (1,807 reviews)
"Staff was great hotel clean close to a lot of dining and stores "
United States
Joseph
The price is NT$2,385
NT$2,800 total
includes taxes & fees
Feb 8 - Feb 9
Hilton Garden Inn Chicago Downtown South Loop
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1,601 reviews)
"Easy check in and out, excellent room service and dining menu."
United States
Kevin Bradford
The price is NT$3,446
NT$4,045 total
includes taxes & fees
Jan 18 - Jan 19
The Wade
Seasonal outdoor pool, sun loungers

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile
3.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (336 reviews)
"Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back!"
United States
Mariana
The price is NT$4,346
NT$5,101 total
includes taxes & fees
Feb 11 - Feb 12
Hilton Grand Vacations Club Chicago Magnificent Mile
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,048 reviews)
"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "
United States
Khalid
The price is NT$3,467
NT$4,997 total
includes taxes & fees
Jan 19 - Jan 20
Sentral Michigan Avenue
Indoor pool

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (4,317 reviews)
"Amazing staff and perfect location "
United States
Brandi
The price is NT$2,489
NT$2,921 total
includes taxes & fees
Jan 27 - Jan 28
Hilton Garden Inn Chicago Downtown/Magnificent Mile
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

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent
"Staff was wonderful and the city is amazin"
Katherine 3-night trip
Posted 16 hours ago
Club Quarters Hotel Wacker at Michigan, Chicago

Frequently asked questions

What are some accommodations with pools in Westchester?
Hilton Chicago/Magnificent Mile Suites: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool, and a health club. Hilton Chicago: Hotel steps from State Street. Provides a full-service spa, an indoor pool, and a 24-hour fitness center. Palmer House a Hilton Hotel: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool, and flat-screen televisions. Club Quarters Hotel Wacker at Michigan, Chicago: Hotel, 14-minute walk from Chicago Riverwalk. Offers 2 restaurants, an indoor pool, and a sauna. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 5-minute walk from Michigan Avenue. Provides a rooftop terrace, a seasonal outdoor pool, and LED televisions.
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.