Find Hotels with a Pool in Westchester, IL

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Check availability on Westchester Hotels with a Pool

Tonight
Dec 6 - Dec 7
Tomorrow
Dec 7 - Dec 8
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Top 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

3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3436)
"Great hotel"
United States
Clara
The price is ￥18,018
￥21,152 total
includes taxes & fees
Dec 21 - Dec 22
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, (1737)
"Staff was courteous, room was clean, convenient location for us. Price was good as well."
United States
Jamie
The price is ￥11,045
￥12,964 total
includes taxes & fees
Jan 6 - Jan 7, 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, (2028)
"Great hotel."
United States
Mario
The price is ￥15,222
￥17,869 total
includes taxes & fees
Dec 22 - Dec 23
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 ￥15,184
￥22,385 total
includes taxes & fees
Jan 3 - Jan 4, 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, (2301)
"Great place - stayed with extended family. Lounge areas and amenities met everyone’s needs "
United States
Elizabeth
The price is ￥15,999
￥23,752 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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, (2117)
"Loved and enjoyed our stay"
United States
Luis
The price is ￥15,921
￥22,575 total
includes taxes & fees
Dec 28 - Dec 29
Palmer House a Hilton Hotel
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, (2945)
"Great location and great staff!!"
United States
lynne
The price is ￥13,980
￥16,410 total
includes taxes & fees
Dec 9 - Dec 10
Aloft Chicago Mag Mile
Indoor pool
The Wade

The Wade

4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1503)
"Great location, walkable to so many area attractions. Would definitely stay here again. "
United States
Debbie
The price is ￥15,668
￥18,393 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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, (5361)
"excellent hotel "
United States
Myounghee
The price is ￥14,648
￥17,196 total
includes taxes & fees
Dec 18 - Dec 19
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, (4222)
"Great location. "
United States
Rodger
The price is ￥12,675
￥14,878 total
includes taxes & fees
Dec 22 - Dec 23
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Thank to Mr.Robert for getting a good room with a beautiful view of the river "
Armando 4-night trip
Posted 5 hours ago
The Royal Sonesta Chicago Downtown

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Frequently asked questions

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