Hotels with Swimming Pools in Westchester

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Check availability on Westchester Hotels with Swimming Pools

Our top choices for Westchester hotels with a pool

Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,065 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is S$126
includes taxes & fees
22 Feb - 23 Feb
Aloft Chicago Mag Mile
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,666 reviews)
"Lovely room, beautiful hotel, wonderful staff, ideal location to navy pier & Michigan Ave. "
United States
Norah
The price is S$132
includes taxes & fees
22 Feb - 23 Feb
The Wade
Indoor pool

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,789 reviews)
"Great stay"
United States
Jennifer
The price is S$133
includes taxes & fees
18 Feb - 19 Feb
Hilton Chicago/Magnificent Mile Suites
Indoor pool, open 5:00 AM to 11:00 PM, pool 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, (3,669 reviews)
"Great place to stay"
United States
suleman
The price is S$185
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, (1,844 reviews)
"Absolutely enjoyed my time here"
United States
Quayshaun
The price is S$114
includes taxes & fees
22 Feb - 23 Feb
Hilton Garden Inn Chicago Downtown South Loop
Indoor pool

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,440 reviews)
"Room was perfect, the staff was so friendly. "
United States
Joseph
The price is S$210
includes taxes & fees
15 Feb - 16 Feb
The Royal Sonesta Chicago River North
Outdoor pool, 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, (2,304 reviews)
"Great staff, room spotless, great price."
United States
Robert
The price is S$136
includes taxes & fees
18 Feb - 19 Feb
DoubleTree by Hilton Chicago - Magnificent 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, (1,078 reviews)
"Amazing location, excellent service and great pool and hot tub. "
United States
Tim
The price is S$200
includes taxes & fees
22 Feb - 23 Feb
Hyatt Centric Chicago Magnificent Mile
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, (4,357 reviews)
"Great staff, great room, and close to everything "
United States
George
The price is S$120
includes taxes & fees
18 Feb - 19 Feb
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Indoor pool

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (5,652 reviews)
"Always a great stay, clean, great breakfast, great pool. "
United States
Zachary
The price is S$152
includes taxes & fees
22 Feb - 23 Feb
Embassy Suites by Hilton Chicago Downtown River North
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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Choose what matters most at hotels with a pool in Westchester

Breakfast included
Hot tub

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Top Westchester Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Great location, beautiful historic hotel with clean, updated rooms. "
Jennifer 4-night trip
Posted 1 day ago
Congress Plaza Hotel

Frequently asked questions

What are some accommodation options with pools in Westchester?
Congress Plaza Hotel: Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool and flat-screen televisions. Hilton Chicago O'Hare Airport: Hotel, 4-minute walk from State Street. Features 2 restaurants, an indoor pool and a health club. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 3-minute walk from Michigan Avenue. Features a snack bar/deli, an indoor pool and complimentary wireless Internet access. Hilton Chicago: Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. Hotel Riu Plaza Chicago: 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 such as United Center, Wrigley Field and Michigan Avenue. 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 plan to visit Westchester in the hottest months of July, August or June, when the average temp is 22°C. Accommodation 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 -1°C.

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