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Check availability on Westchester Hotels with Pool

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
8.8 out of 10, Excellent, (3223)
"Great stay "
shanae
The price is ฿6,050
฿7,102 total
includes taxes & fees
16 Nov - 17 Nov
voco Chicago Downtown - Riverwalk by IHG
1 bedroom, premium bedding, down duvets, pillow-top beds
The Wade
The Wade
4.5 star property
8.4 out of 10, Very good, (1379)
"Great place to stay"
Adam
The price is ฿4,391
฿5,155 total
includes taxes & fees
2 Nov - 3 Nov
The Wade
Indoor pool
Best Western River North Hotel
Best Western River North Hotel
2.5 star property
7.8 out of 10, Good, (1028)
"Great stay"
Bart
The price is ฿3,290
฿3,862 total
includes taxes & fees
10 Nov - 11 Nov
Best Western River North Hotel
Pool
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
8.8 out of 10, Excellent, (1695)
"Excellent hotel in a wonderful location of Chicago!"
Amy
The price is ฿3,567
฿4,187 total
includes taxes & fees
10 Nov - 11 Nov
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
9.2 out of 10, Wonderful, (2198)
"Great location, and value for money."
Anil
The price is ฿7,192
฿9,494 total
includes taxes & fees
30 Oct - 31 Oct
The Royal Sonesta Chicago River North
Indoor pool, open 7:00 AM to 10:00 PM, pool loungers
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2869)
"Had a great stay!"
Josh
The price is ฿4,489
฿5,270 total
includes taxes & fees
10 Nov - 11 Nov
Aloft Chicago Mag Mile
Seasonal outdoor pool, open 10:00 AM to 10:00 PM, pool loungers
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (171)
"This place has everything for a multi-night stay."
Dane
Kasa River North Chicago
Indoor pool
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.6 out of 10, Excellent, (5111)
"Great place, good breakfast and the location "
NATIA
The price is ฿4,673
฿5,485 total
includes taxes & fees
16 Nov - 17 Nov
Embassy Suites by Hilton Chicago Downtown River North
Indoor pool
Holiday Inn Chicago Dwtn - The Mart by IHG
Holiday Inn Chicago Dwtn - The Mart by IHG
3.0 star property
8.8 out of 10, Excellent, (1943)
"Very Nice Hotel in a great location."
Stephen
The price is ฿5,986
฿7,027 total
includes taxes & fees
9 Nov - 10 Nov
Holiday Inn Chicago Dwtn - The Mart by IHG
Indoor pool
Hyatt Centric Chicago Magnificent Mile
Hyatt Centric Chicago Magnificent Mile
4.0 star property
9.0 out of 10, Wonderful, (1040)
"Great place to stay"
Carolyn
The price is ฿5,497
฿7,408 total
includes taxes & fees
30 Oct - 31 Oct
Hyatt Centric Chicago 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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Spent a night for our 14th anniversary. The staff was very thoughtful and kind. We appreciate the staff and room!"
Allen 1-night trip
Posted 3 days ago
Crowne Plaza Chicago West Loop by IHG

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Frequently asked questions

What are some accommodation options with pools in Westchester?
Congress Plaza Hotel: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool and flat-screen televisions. Freehand Chicago: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool and a sauna. Hilton Chicago/Magnificent Mile Suites: Hotel, 4-minute walk from Michigan Avenue. Features complimentary high-speed (wired) Internet access, an indoor pool and LCD televisions. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool and complimentary wireless Internet access. InterContinental Chicago Magnificent Mile by IHG: Hotel, 3-minute walk from Merchandise Mart. Provides 2 restaurants, an indoor pool and a sauna.
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 Navy Pier. 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.