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Check availability on Westchester Hotels with Pool

Our top choices for Westchester hotels with a pool

Indoor pool

Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport
2.5 star property
Schiller Park
9.2 out of 10, Wonderful, (2,291 reviews)
  • cleanliness
    Splash into cool escape at Chicago O'Hare's serene indoor pool, perfect for year-round laps and leisure dips.
"the pool was fantastically relaxing and a peaceful experience"
United States
Eugenia
The price is ฿4,519
฿5,196 total
includes taxes & fees
25 May - 26 May
Hampton Inn Chicago-O'Hare International Airport
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers

Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport
3.0 star property
Rosemont
8.4 out of 10, Very good, (3,387 reviews)
  • cleanliness
    Dive into pure bliss at this Chicago hotel's indoor pool sanctuary with loungers for post-adventure relaxation.
"And the pool was nice and clean"
United States
Cecilia
The price is ฿3,804
฿4,336 total
includes taxes & fees
26 May - 27 May
Hyatt Place Chicago/O'Hare Airport
Indoor pool, open 8:00 AM to 11:00 PM, pool loungers

Holiday Inn Express & Suites Bensenville - O'Hare by IHG

Holiday Inn Express & Suites Bensenville - O'Hare by IHG
3.0 star property
Bensenville
8.8 out of 10, Excellent, (1,010 reviews)
  • cleanliness
    Splash into relaxation at this airport hotel with an indoor pool and comfy sun loungers.
"the pool was the highlight for our two year old grandson"
United States
James
The price is ฿3,706
฿4,225 total
includes taxes & fees
25 May - 26 May
Holiday Inn Express & Suites Bensenville - O'Hare by IHG
Fitness facility

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,623 reviews)
  • cleanliness
    Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.
"the pool was nice and clean"
Canada
Dana
The price is ฿7,286
฿9,822 total
includes taxes & fees
26 May - 27 May
Sheraton Grand Chicago Riverwalk
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, (2,479 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
"Great location, great bar, helpful staff, relaxing pool amongst the other sky scrapers."
United Kingdom
David
The price is ฿5,347
฿6,357 total
includes taxes & fees
25 May - 26 May
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool

Homewood Suites by Hilton Chicago-Downtown

Homewood Suites by Hilton Chicago-Downtown
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,211 reviews)
"Great location with a very nice breakfast spread and a great top floor pool"
United States
Alan
The price is ฿6,082
฿7,231 total
includes taxes & fees
25 May - 26 May
Homewood Suites by Hilton Chicago-Downtown
Indoor pool

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2,858 reviews)
  • cleanliness
    Chicago hotel offers refreshing stays with indoor pool, fitness centre, and walkable Michigan Avenue access.
"Pool was great after a long day of driving."
United States
Stephanie
The price is ฿4,786
฿6,644 total
includes taxes & fees
26 May - 27 May
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Indoor pool

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,597 reviews)
  • cleanliness
    Stylish indoor pool retreat in city centre Chicago makes luxury laps a breeze after sightseeing.
"The view from the pool room is also beautiful."
United States
Rachelle
The price is ฿5,365
฿7,419 total
includes taxes & fees
26 May - 27 May
The Royal Sonesta Chicago River North
Indoor pool, pool loungers

Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    Splash into urban relaxation at this West Loop hotel's stylish indoor pool, where sun loungers invite post-sightseeing unwinding.
"Pool was great for kids!"
United States
Erin
The price is ฿6,022
฿7,160 total
includes taxes & fees
25 May - 26 May
Hampton Inn Chicago West Loop Fulton Market Area
Indoor pool, pool loungers

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Swim year-round at the urban indoor pool oasis with sun loungers and city centre Chicago views.
"This is probably one of the cleanest hotels we have ever stayed in. The room was so clean along with the lobby. Breakfast was delicious! Our view was beautiful and the best thing was we were so close to the united center and it was an easy drive there and back. The hotel staff is extremely friendly and helpful. We will definitely stay here again! The price along with everything this hotel has to offer is worth it. I highly recommend this hotel!"
United States
James
The price is ฿5,003
฿5,948 total
includes taxes & fees
26 May - 27 May
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

6/10 Okay
"The room was clean but pretty basic. It was good overall but we did have an issue with the a/c switching off in the middle of the night. Unfortunately the hotel didn’t have any fans to remedy that situation. Other than that we had a very enjoyable stay. The location is great! "
Madan 3-night trip
Posted 2 hours ago
Hotel Felix River North/Magnificent Mile

Frequently asked questions

What are some accommodation options with pools in Westchester?
Congress Plaza Hotel: Hotel, 3-minute walk from Merchandise Mart. Features 2 restaurants, an indoor pool and a sauna. River Hotel: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool and a health club. Hotel Riu Plaza Chicago: Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. 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. Hotel Felix River North/Magnificent Mile: Hotel, 4-minute walk from Michigan Avenue. Provides full, 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 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.