Search Hotels with Pool in Westchester

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Check availability on Westchester Hotels with Pool

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Westchester Hotels with Pool

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, (3433)
"Great hotel"
United States
Clara
The price is 2.721.694 ₫
3.194.996 ₫ total
includes taxes & fees
25 Dec - 26 Dec
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, (1734)
"Staff was courteous, room was clean, convenient location for us. Price was good as well."
United States
Jamie
The price is 1.877.758 ₫
2.203.992 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Garden Inn Chicago Downtown South Loop
Indoor pool
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, (2025)
"Great hotel."
United States
Mario
The price is 2.299.551 ₫
2.699.442 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Holiday Inn Chicago Dwtn - The Mart by IHG
Indoor pool
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1045)
"Great Hotel!"
United States
Wendy
The price is 2.577.765 ₫
3.800.028 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Hyatt Centric Chicago Magnificent Mile
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, (2296)
"Great place - stayed with extended family. Lounge areas and amenities met everyone’s needs "
United States
Elizabeth
The price is 2.700.824 ₫
4.014.369 ₫ total
includes taxes & fees
7 Dec - 8 Dec
The Royal Sonesta Chicago River North
Indoor pool
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2116)
"Loved and enjoyed our stay"
United States
Luis
The price is 2.703.028 ₫
3.832.360 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Palmer House a Hilton Hotel
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, (2944)
"Great location and great staff!!"
United States
lynne
The price is 2.373.390 ₫
2.786.121 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Aloft Chicago Mag Mile
Indoor pool
The Wade

The Wade

4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1501)
"Great location, walkable to so many area attractions. Would definitely stay here again. "
United States
Debbie
The price is 2.663.471 ₫
3.126.650 ₫ total
includes taxes & fees
10 Dec - 11 Dec
The Wade
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, (5354)
"excellent hotel "
United States
Myounghee
The price is 2.486.974 ₫
2.919.459 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Embassy Suites by Hilton Chicago Downtown River North
Indoor pool
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, (4215)
"Location is perfect "
United States
Deyana
The price is 2.172.970 ₫
2.550.850 ₫ total
includes taxes & fees
22 Dec - 23 Dec
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

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Frequently asked questions

What is there to see and do in Westchester?
While you're in the area, consider exploring places such as 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 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.