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Check availability on Westchester Hotels with Pool

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, (3,052 reviews)
"All around a nice stay for the holiday "
United States
Alec
The price is ฿2,540
฿2,982 total
includes taxes & fees
1 Feb - 2 Feb
Aloft Chicago Mag Mile
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, (2,253 reviews)
"Great hotel "
United States
Jeffrey
The price is ฿2,682
฿3,149 total
includes taxes & fees
1 Feb - 2 Feb
DoubleTree by Hilton Chicago - Magnificent Mile
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, (3,615 reviews)
"Great place "
United States
Ricardo
The price is ฿3,523
฿4,136 total
includes taxes & fees
16 Feb - 17 Feb
voco Chicago Downtown - Riverwalk by IHG
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, (3,740 reviews)
"Great stay!!!"
United States
Lorenzo Martrel
The price is ฿2,527
฿2,967 total
includes taxes & fees
1 Feb - 2 Feb
Hilton Chicago/Magnificent Mile Suites
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, (1,819 reviews)
"Always a great stay!"
United States
ANN
The price is ฿2,373
฿2,786 total
includes taxes & fees
10 Feb - 11 Feb
Hilton Garden Inn Chicago Downtown South Loop
Indoor pool

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,069 reviews)
"Amazing location, excellent service and great pool and hot tub. "
United States
Tim
The price is ฿3,460
฿4,985 total
includes taxes & fees
1 Feb - 2 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, (4,334 reviews)
"All things about this hotel was good from the location to the staff"
United States
Cisco
The price is ฿2,682
฿3,149 total
includes taxes & fees
1 Feb - 2 Feb
Hilton Garden Inn Chicago Downtown/Magnificent Mile
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, (2,123 reviews)
"Excellent hotel plus very good location"
Canada
Tomas Colocol
The price is ฿3,649
฿4,283 total
includes taxes & fees
6 Feb - 7 Feb
Holiday Inn Chicago Dwtn - The Mart by IHG
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, (1,669 reviews)
"Would definitely stay again…location was perfect "
United States
Ashley
The price is ฿3,183
฿3,737 total
includes taxes & fees
5 Feb - 6 Feb
Courtyard by Marriott Chicago Magnificent Mile
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, (2,194 reviews)
"It was a good stay."
United States
Manish Mani
The price is ฿2,554
฿2,998 total
includes taxes & fees
8 Feb - 9 Feb
Homewood Suites by Hilton Chicago Downtown South Loop
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Staff were friendly & helpful "
Rosanne 3-night trip
Posted 18 hours ago
Hilton Chicago/Magnificent Mile Suites

Frequently asked questions

What are some accommodation options 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 centre. 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 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.