Westchester Hotels with Swimming Pool

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Westchester hotels with a pool

Indoor pool
The Wade

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1545)
"Great staff and great location. "
United States
Joe
The price is RM377
RM442 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Wade
Indoor pool, open 7:00 AM to 10:00 PM, pool loungers
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2996)
"Great place to stay"
United States
Elisha
The price is RM348
RM409 total
includes taxes & fees
22 Jan - 23 Jan 2026
Aloft Chicago Mag Mile
Indoor pool, open 5:00 AM to 11:00 PM, pool loungers
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3533)
"Really nice hotel"
United States
Saulius
The price is RM470
RM552 total
includes taxes & fees
26 Jan - 27 Jan 2026
voco Chicago Downtown - Riverwalk by IHG
Outdoor pool, pool cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2211)
"It was a beautiful stay "
United States
Donald
The price is RM345
RM405 total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1060)
"Clean room, clean hotel, wonderful restaurant/bar. AMAZING location! "
United States
Rebecca
The price is RM397
RM585 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hyatt Centric Chicago Magnificent Mile
Indoor pool
The Royal Sonesta Chicago 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, (2343)
"Great property and room"
United States
Steven
The price is RM450
RM657 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Royal Sonesta Chicago River North
Pool
Hilton Garden Inn Chicago Downtown South Loop

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, (1791)
"Great place to stay! Near all the sites to see!"
United States
Rafael
The price is RM306
RM359 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Garden Inn Chicago Downtown South Loop
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1800)
"Great hotel, close to shopping and restaurants, excellent customer service, highly recommend."
United States
Gina
The price is RM541
RM740 total
includes taxes & fees
2 Jan - 3 Jan 2026
Radisson Blu Aqua Hotel Chicago
Indoor pool
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (4287)
"Amazing staff and perfect location "
United States
Brandi
The price is RM316
RM370 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Indoor pool
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

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, (2769)
"Excellent place to stay "
United States
Teniesha
The price is RM299
RM470 total
includes taxes & fees
6 Jan - 7 Jan 2026
Embassy Suites by Hilton Chicago Downtown 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.
View all properties

Top Westchester Hotel Reviews

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Staff were very friendly and helpful. I would recommend this hotel to friends. Conveniently located and walkable to area attractions."
Matthew 1-night trip
Posted 2 days ago
Eurostars Magnificent Mile

Frequently asked questions

What are some accommodation options with pools in Westchester?
Hilton Chicago/Magnificent Mile Suites: Hotel steps from State Street. Offers a full-service spa, an indoor pool and a 24-hour fitness centre. Palmer House a Hilton Hotel: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool and a health club. Silversmith Hotel Chicago Downtown: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool and flat-screen televisions. Club Quarters Hotel Wacker at Michigan, Chicago: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool and a sauna. Hilton Chicago: Hotel, 13-minute walk from Chicago Riverwalk. Offers 2 restaurants, an indoor pool and a sauna.
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