Hotels with Swimming Pools in Westchester

  • 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
30 Mar - 31 Mar
Tomorrow
31 Mar - 1 Apr
This weekend
3 Apr - 5 Apr
Next weekend
10 Apr - 12 Apr

Our top choices for Westchester hotels with a pool

Indoor pool, pool loungers

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,001 reviews)
"Clean Room, Friendly and attentive staff"
United States
Felix
The price is S$291
includes taxes & fees
4 Apr - 5 Apr
Renaissance Chicago Downtown Hotel
Indoor pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,343 reviews)
"Beautiful property, great resturant on site, an the pool and spa was amazing."
United States
Tim
The price is S$280
includes taxes & fees
5 Apr - 6 Apr
Palmer House a Hilton Hotel
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, (3,167 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is S$165
includes taxes & fees
5 Apr - 6 Apr
Aloft Chicago Mag Mile
Indoor pool

JW Marriott Chicago

JW Marriott Chicago
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,002 reviews)
"Hot tubs was the best part!! Super hot water "
United States
Myeisha
The price is S$382
includes taxes & fees
10 Apr - 11 Apr
JW Marriott 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, (2,390 reviews)
"Loved this hotel!"
United States
Ellen
The price is S$166
includes taxes & fees
5 Apr - 6 Apr
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,116 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is S$216
includes taxes & fees
1 Apr - 2 Apr
Sentral Michigan Avenue
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,763 reviews)
"Staff was friendly, explained the hotel and amenities well. Great location."
United States
Mary
The price is S$256
includes taxes & fees
27 Apr - 28 Apr
The Wade
Indoor pool

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,076 reviews)
"Clean room, very new, excellent stay"
United States
Anthony
The price is S$256
includes taxes & fees
6 Apr - 7 Apr
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, (1,004 reviews)
"Super cute hotel. Great bar and food "
United States
Patricia
The price is S$253
includes taxes & fees
5 Apr - 6 Apr
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, (902 reviews)
"Clean room, Great amenities and super helpful and accommodating staff"
United States
Bella
The price is S$274
includes taxes & fees
12 Apr - 13 Apr
Level Chicago - River North
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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Great location, friendly staff, complimentary full breakfast, evening drinks and snacks. A great place to stay with a family!"
Maureen 2-night trip
Posted 1 hour ago
Embassy Suites by Hilton Chicago Downtown River North

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, 3-minute walk from Michigan Avenue. Features a snack bar/deli, an indoor pool and complimentary wireless Internet access. Hilton Chicago/Magnificent Mile Suites: Hotel, 8-minute walk from Lake Michigan. Offers a 24-hour fitness centre, an indoor pool and flat-screen televisions. Hilton Chicago O'Hare Airport: Hotel, 12-minute walk from Millennium Park. Features 2 restaurants, an indoor pool and a health club.
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