Westchester Hotel with Pool

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Check availability on Westchester Hotel with Pool

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

Our top choices for Westchester hotels with a pool

Indoor pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,465 reviews)
  • cleanliness
    Dive into urban tranquility at the Palmer House pool, where historic charm meets modern luxury.
The price is HK$2,291
HK$2,957 total
includes taxes & fees
21 Jun - 22 Jun
Palmer House a Hilton Hotel
Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,256 reviews)
  • cleanliness
    Splash into the city at this city centre hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.
The price is HK$1,763
HK$2,096 total
includes taxes & fees
14 Jun - 15 Jun
Aloft by Marriott 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, (2,492 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is HK$1,678
HK$1,995 total
includes taxes & fees
14 Jun - 15 Jun
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,943 reviews)
  • cleanliness
    Luxurious indoor and seasonal outdoor pools form a relaxing oasis near Millennium Park and Michigan Avenue.
The price is HK$1,992
HK$2,611 total
includes taxes & fees
14 Jun - 15 Jun
Radisson Blu Aqua Hotel Chicago
Seasonal outdoor pool

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.
The price is HK$2,108
HK$2,737 total
includes taxes & fees
21 Jun - 22 Jun
The Hoxton Chicago
Fitness facility

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,643 reviews)
  • cleanliness
    Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.
The price is HK$2,476
HK$3,224 total
includes taxes & fees
14 Jun - 15 Jun
Sheraton Grand Chicago Riverwalk
Indoor pool

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,098 reviews)
  • cleanliness
    Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, hot tub haven, and 24-hour fitness centre.
The price is HK$1,661
HK$2,208 total
includes taxes & fees
14 Jun - 15 Jun
Hyatt Centric Chicago Magnificent Mile
Indoor pool

JW Marriott Chicago

JW Marriott Chicago
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Sleek indoor pool sanctuary opens onto Chicago adventures in this luxury retreat.
The price is HK$2,186
HK$2,878 total
includes taxes & fees
28 Jun - 29 Jun
JW Marriott Chicago
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, (2,012 reviews)
  • cleanliness
    Dive into city centre luxury with a rejuvenating pool experience close to Chicago landmarks.
The price is HK$1,825
HK$2,169 total
includes taxes & fees
15 Jun - 16 Jun
Hilton Garden Inn Chicago Downtown South Loop
Indoor pool

Courtyard by Marriott Chicago Downtown River North

Courtyard by Marriott Chicago Downtown River North
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Refreshing plunges await at this city centre Chicago hotel with an indoor pool open from dawn to dusk.
The price is HK$1,504
HK$1,788 total
includes taxes & fees
14 Jun - 15 Jun
Courtyard by Marriott 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

Top Westchester Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Room was clean, staff was super friendly and helpful. Definitely going to be booking here more often for events"
Luna 1-night trip
Posted less than an hour ago
Hilton Chicago

Frequently asked questions

What are some accommodation options with pools in Westchester?
Congress Plaza Hotel: Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool and a sauna. Hotel Riu Plaza Chicago: Hotel, 3-minute walk from Michigan Avenue. Features a snack bar/deli, an indoor pool and complimentary wireless Internet access. The Chicago Hotel Collection - Magnificent Mile: Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. Hotel Felix River North/Magnificent Mile: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool and flat-screen televisions. River Hotel: Hotel, 5-minute walk from Michigan Avenue. Offers 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, Navy Pier 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.

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