Westchester Hotel with 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 Hotel with Pool

Our top choices for Westchester hotels with a pool

Indoor pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,306 reviews)
"Excellent stay, we loved it "
United States
Melani
The price is HK$1,179
HK$1,579 total
includes taxes & fees
7 Mar - 8 Mar
Palmer House a Hilton Hotel
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,683 reviews)
"Thoroughly enjoyed my stay at The Wade"
United States
Danielle
The price is HK$774
HK$908 total
includes taxes & fees
1 Mar - 2 Mar
The Wade
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, (3,093 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is HK$672
HK$789 total
includes taxes & fees
23 Feb - 24 Feb
Aloft Chicago Mag Mile
Indoor pool, pool loungers

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,004 reviews)
"Wonderful location and staff was top notch."
United States
M Kim
The price is HK$1,305
HK$1,766 total
includes taxes & fees
27 Feb - 28 Feb
Renaissance Chicago Downtown Hotel
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, (2,322 reviews)
"Great staff, room spotless, great price."
United States
Robert
The price is HK$763
HK$895 total
includes taxes & fees
26 Feb - 27 Feb
DoubleTree by Hilton Chicago - Magnificent Mile
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, (1,865 reviews)
"Absolutely enjoyed my time here"
United States
Quayshaun
The price is HK$666
HK$782 total
includes taxes & fees
1 Mar - 2 Mar
Hilton Garden Inn Chicago Downtown South Loop
Indoor pool

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,079 reviews)
"Amazing location, excellent service and great pool and hot tub. "
United States
Tim
The price is HK$992
HK$1,394 total
includes taxes & fees
26 Feb - 27 Feb
Hyatt Centric Chicago Magnificent Mile
Seasonal outdoor pool

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,006 reviews)
"Amazing, I loved my stay"
United States
Valerie
The price is HK$1,129
HK$1,555 total
includes taxes & fees
22 Mar - 23 Mar
The Hoxton Chicago
Seasonal outdoor pool

Level Chicago - River North

Level Chicago - River North
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (849 reviews)
"Great stay. Would come again. "
United States
Gracie
Level Chicago - River North
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,086 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is HK$857
HK$1,235 total
includes taxes & fees
22 Feb - 23 Feb
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Clean, quiet, and conveniently located. Friendly staff as well. "
Christopher 1-night trip
Posted 16 hours ago
Eurostars Magnificent Mile

Frequently asked questions

What are some accommodation options with pools in Westchester?
Congress Plaza Hotel: Hotel, 4-minute walk from State Street. Provides 2 restaurants, an indoor pool and a health club. Hotel Riu Plaza Chicago: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool and flat-screen televisions. Hilton Chicago: Hotel steps from 875 North Michigan Avenue. Features flat-screen televisions and an indoor pool. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool and complimentary wireless Internet access. Hilton Chicago O'Hare Airport: Hotel, 5-minute walk from Michigan Avenue. Provides 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 Navy Pier. 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