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Our top choices for Westchester hotels with a pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,423 reviews)
  • cleanliness
    Dive into urban tranquility at the Palmer House pool, where historic charm meets modern luxury.
The price is ฿4,809
฿6,685 total
includes taxes & fees
25 May - 26 May
Palmer House a Hilton Hotel

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, (1,969 reviews)
  • cleanliness
    Dive into city centre luxury with a rejuvenating pool experience close to Chicago landmarks.
The price is ฿4,256
฿5,061 total
includes taxes & fees
26 May - 27 May
Hilton Garden Inn Chicago Downtown South Loop

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,208 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 ฿4,845
฿5,760 total
includes taxes & fees
10 May - 11 May
Aloft Chicago Mag Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,091 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 ฿5,495
฿7,488 total
includes taxes & fees
25 May - 26 May
Hyatt Centric Chicago Magnificent Mile

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.
The price is ฿4,946
฿6,834 total
includes taxes & fees
10 May - 11 May
The Hoxton Chicago

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, (1,001 reviews)
  • cleanliness
    Refreshing plunges await at this city centre Chicago hotel with an indoor pool open from dawn to dusk.
The price is ฿5,900
฿7,016 total
includes taxes & fees
9 May - 10 May
Courtyard by Marriott Chicago Downtown River North

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,625 reviews)
  • cleanliness
    Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.
The price is ฿7,051
฿9,553 total
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Splash into pure relaxation at this city centre hotel's indoor pool with loungers and fitness centre access.
The price is ฿7,511
฿10,090 total
includes taxes & fees
8 May - 9 May
Renaissance Chicago Downtown Hotel

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, (5,913 reviews)
  • cleanliness
    Slip into a holiday state of mind at Chicago's urban retreat with a sparkling indoor pool.
The price is ฿4,671
฿5,553 total
includes taxes & fees
25 May - 26 May
Embassy Suites by Hilton Chicago Downtown River North

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,564 reviews)
  • cleanliness
    Stylish indoor pool retreat in city centre Chicago makes luxury laps a breeze after sightseeing.
The price is ฿4,845
฿6,801 total
includes taxes & fees
25 May - 26 May
The Royal Sonesta Chicago 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.

Choose what matters most at hotels with a pool in Westchester

Top Westchester Hotel Reviews

Frequently asked questions

What are some accommodation options with pools in Westchester?
Congress Plaza Hotel: Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. River Hotel: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool and flat-screen televisions. Hotel Felix River North/Magnificent Mile: Hotel, 3-minute walk from Millennium Park. Provides a full-service spa, an indoor pool and a 24-hour fitness centre. Club Quarters Hotel, Central Loop, Chicago: Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool and complimentary wireless Internet access. Hilton Chicago/Magnificent Mile Suites: Hotel, 12-minute walk from Millennium Park. 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 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.