Westchester Hotels with Swimming Pool

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Westchester Hotels with Swimming Pools

Tonight
5 Mar - 6 Mar
Tomorrow
6 Mar - 7 Mar
This weekend
6 Mar - 8 Mar
Next weekend
13 Mar - 15 Mar

Our top choices for Westchester hotels with a pool

Indoor pool

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,872 reviews)
The price is RM409
RM480 total
includes taxes & fees
18 Mar - 19 Mar
Hilton Chicago/Magnificent Mile Suites
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, (3,128 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 RM410
RM482 total
includes taxes & fees
8 Mar - 9 Mar
Aloft Chicago Mag Mile
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,708 reviews)
  • cleanliness
    Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.
The price is RM429
RM504 total
includes taxes & fees
22 Mar - 23 Mar
The Wade
Seasonal outdoor pool

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,009 reviews)
  • cleanliness
    Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.
The price is RM599
RM819 total
includes taxes & fees
8 Mar - 9 Mar
The Hoxton Chicago
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, (2,344 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is RM417
RM489 total
includes taxes & fees
22 Mar - 23 Mar
DoubleTree by Hilton Chicago - Magnificent Mile
Seasonal outdoor pool

Level Chicago - River North

Level Chicago - River North
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (863 reviews)
  • cleanliness
    Summer splashes and cityscape views await at this Chicago hotel's seasonal rooftop pool.
Level Chicago - River North
Indoor pool

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, (5,714 reviews)
  • cleanliness
    Slip into a holiday state of mind at Chicago's urban retreat with a sparkling indoor pool.
The price is RM515
RM604 total
includes taxes & fees
22 Mar - 23 Mar
Embassy Suites by Hilton Chicago Downtown River North
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, (1,127 reviews)
The price is RM453
RM531 total
includes taxes & fees
22 Mar - 23 Mar
Homewood Suites by Hilton Chicago-Downtown
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, (1,878 reviews)
  • cleanliness
    Dive into city centre luxury with a rejuvenating pool experience close to Chicago landmarks.
The price is RM466
RM547 total
includes taxes & fees
18 Mar - 19 Mar
Hilton Garden Inn Chicago Downtown South Loop
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,098 reviews)
  • cleanliness
    Indoor pool oasis at upscale Michigan Avenue aparthotel offers year-round swimming enjoyment.
The price is RM499
RM701 total
includes taxes & fees
9 Mar - 10 Mar
Sentral Michigan Avenue
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.
View all properties

Choose what matters most at hotels with a pool in Westchester

Breakfast included
Hot tub

Top Westchester Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Clean room spacious friendly staff"
Theresa 4-night trip
Posted 2 hours ago
Hilton Chicago/Magnificent Mile Suites

Frequently asked questions

What are some accommodation options with pools in Westchester?
Congress Plaza Hotel: Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool and flat-screen televisions. Hotel Riu Plaza Chicago: Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from State Street. Features 2 restaurants, an indoor pool and a health club. Hilton Chicago/Magnificent Mile Suites: Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool and complimentary wireless Internet access. Eurostars Magnificent Mile: 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.

Explore a world of travel with Expedia