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, (2,238 reviews)
"Great hotel "
United States
Jeffrey
The price is AED 313
AED 368 total
includes taxes & fees
1 Feb - 2 Feb
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, (3,035 reviews)
"All around a nice stay for the holiday "
United States
Alec
The price is AED 278
AED 326 total
includes taxes & fees
25 Jan - 26 Jan
Aloft Chicago Mag 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, (3,599 reviews)
"Great location and breakfast.. can be a bit pricey but worth it. "
Canada
Shaurya
The price is AED 426
AED 500 total
includes taxes & fees
15 Feb - 16 Feb
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, (1,808 reviews)
"Always a great stay!"
United States
ANN
The price is AED 277
AED 325 total
includes taxes & fees
8 Feb - 9 Feb
Hilton Garden Inn Chicago Downtown South Loop
View from room

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,717 reviews)
"Great stay!!!"
United States
Lorenzo Martrel
The price is AED 295
AED 346 total
includes taxes & fees
25 Jan - 26 Jan
Hilton Chicago/Magnificent Mile Suites
Indoor pool

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,068 reviews)
"Amazing location, excellent service and great pool and hot tub. "
United States
Tim
The price is AED 360
AED 530 total
includes taxes & fees
25 Jan - 26 Jan
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, (1,673 reviews)
"Would definitely stay again…location was perfect "
United States
Ashley
The price is AED 372
AED 436 total
includes taxes & fees
5 Feb - 6 Feb
Courtyard by Marriott Chicago Magnificent Mile
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1,603 reviews)
"Easy check in and out, excellent room service and dining menu."
United States
Kevin Bradford
The price is AED 400
AED 470 total
includes taxes & fees
18 Jan - 19 Jan
The Wade
Pool

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, (2,189 reviews)
"It was a good stay."
United States
Manish Mani
The price is AED 298
AED 350 total
includes taxes & fees
16 Feb - 17 Feb
Homewood Suites by Hilton Chicago Downtown South Loop
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 AED 403
AED 581 total
includes taxes & fees
19 Jan - 20 Jan
Sentral Michigan Avenue
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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Great stay. "
Christopher E. 3-night trip
Posted 10 hours ago
Embassy Suites by Hilton Chicago Downtown River North

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Frequently asked questions

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