Find Hotels with a Pool in Westchester, IL

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Check availability on Westchester Hotels with a Pool

Tonight
Nov 22 - Nov 23
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Nov 23 - Nov 24
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Nov 28 - Nov 30
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Dec 5 - Dec 7

Top Westchester Hotels with a Pool

Indoor pool
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 star property
Downtown Chicago
  • Indoor pool
  • Near the beach
9.2 out of 10, Wonderful, (2268)
Sink into luxurious pool loungers at the inviting indoor sanctuary after exploring nearby Michigan Avenue. Featuring a 24-hour fitness center, on-site restaurant, and terrace, this hotel perfectly combines aquatic relaxation with urban adventure.
$130 nightly
The price is $153
Nov 26 - Nov 27
Total with taxes and fees
The Royal Sonesta Chicago River North
Indoor pool
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
Downtown Chicago
  • Indoor pool
  • Near the beach
8.4 out of 10, Very Good, (4188)
Pool enthusiasts revel in year-round swimming at this urban retreat's indoor aquatic haven. Just steps from Michigan Avenue and Millennium Park, guests enjoy Weber Grill dining, convenient shopping, and spacious accommodations.
$80 nightly
The price is $94
Dec 7 - Dec 8
Total with taxes and fees
Hilton Garden Inn Chicago Downtown/Magnificent Mile
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
  • Indoor pool
  • Pool loungers
  • Near the beach
8.6 out of 10, Excellent, (2927)
Dive into relaxation at the inviting indoor pool, perfectly complementing days spent exploring nearby Millennium Park and Navy Pier. Sun loungers provide comfortable respite, while the fitness center with city views offers 24-hour workout options.
$98 nightly
The price is $115
Dec 7 - Dec 8
Total with taxes and fees
Aloft Chicago Mag Mile
Indoor pool
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
Downtown Chicago
  • Indoor pool
  • Near the beach
8.6 out of 10, Excellent, (5285)
Swimming becomes a highlight at the indoor pool sanctuary, where adults supervise children in a pristine environment. After water fun, guests explore Chicago's vibrant riverfront location, just steps from Michigan Avenue shopping and Millennium Park attractions.
$87 nightly
The price is $102
Dec 21 - Dec 22
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North
Indoor pool
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
  • Indoor pool
  • Near the beach
  • Full-service spa
8.4 out of 10, Very Good, (2082)
Sophisticated swimmers relish the year-round indoor pool at this historic treasure near Millennium Park. After invigorating laps, guests can indulge in spa treatments, workout at the 24-hour health club, or explore nearby Chicago landmarks.
$128 nightly
The price is $145
Dec 21 - Dec 22
Total with taxes and fees
Palmer House a Hilton Hotel
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
  • Indoor pool
  • Pool loungers
  • Near the beach
8.8 out of 10, Excellent, (3383)
Swimmers delight in the spacious indoor pool with glass roof, accessing refreshing waters from early morning until late evening. After laps, guests unwind on comfortable loungers or detoxify in the sauna before dining at the riverside restaurant.
$103 nightly
The price is $121
Nov 25 - Nov 26
Total with taxes and fees
voco Chicago Downtown - Riverwalk by IHG
1 bedroom, premium bedding, down comforters, pillowtop beds
The Wade

The Wade

4.5 star property
Downtown Chicago
  • Indoor pool
  • Near the beach
8.4 out of 10, Very Good, (1464)
Sparkling waters beckon in the sleek indoor pool, a serene oasis amid Chicago's urban energy. Guests appreciate the 5:00 AM to 11:00 PM access, perfect for refreshing dips before exploring Navy Pier or after fitness classes at the 24-hour gym.
$103 nightly
The price is $121
Nov 27 - Nov 28
Total with taxes and fees
The Wade
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3.0 star property
Downtown Chicago
  • Pool
  • Pet friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Gym
8.8 out of 10, Excellent, (1720)
Swimming laps in the refreshing pool creates the perfect interlude between city adventures and relaxation. Minutes from Soldier Field and downtown attractions, this hotel combines Asian cuisine at Shang Noodle with thoughtful amenities for a complete urban retreat.
$79 nightly
The price is $93
Dec 15 - Dec 16
Total with taxes and fees
Hilton Garden Inn Chicago Downtown South Loop
Outdoor pool, cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Downtown Chicago
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • Near the beach
8.8 out of 10, Excellent, (2144)
Poolside bliss awaits with shaded cabanas, comfortable loungers, and refreshing cocktails from the bar. After swimming, guests can explore Michigan Avenue's attractions, dine at HotHouse restaurant, or energize in the fitness center.
$98 nightly
The price is $115
Dec 7 - Dec 8
Total with taxes and fees
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4.0 star property
Downtown Chicago
  • Indoor pool
  • Near the beach
  • Hot tub
9.0 out of 10, Wonderful, (1038)
Bubbling relaxation awaits in the pristine indoor pool and soothing hot tub, perfect complements to an invigorating workout in the state-of-the-art fitness center. Steps from Chicago's Riverwalk and Millennium Park, this hotel combines aquatic tranquility with urban adventure.
$123 nightly
The price is $144
Dec 7 - Dec 8
Total with taxes and fees
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

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Clean, large room, complementary breakfast! Great location."
Melissa 2-night trip
Posted 6 hours ago
The Whitehall Hotel, BW Premier Collection

Frequently asked questions

What are some accommodations with pools in Westchester?
Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool, and flat-screen televisions. Palmer House a Hilton Hotel: Hotel steps from State Street. Offers a full-service spa, an indoor pool, and a 24-hour fitness center. Hilton Chicago/Magnificent Mile Suites: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. CitizenM Chicago Downtown: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool, and a health club. Warwick Allerton - Chicago: Hotel, 8-minute walk from Lake Michigan. Features a 24-hour fitness center, an indoor pool, and flat-screen televisions.
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.

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