Hotels with Pool & Resorts in Westchester from NZ$264

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Check availability on Westchester Hotels with Pool

Tonight
8 Apr - 9 Apr
Tomorrow
9 Apr - 10 Apr
This weekend
10 Apr - 12 Apr
Next weekend
17 Apr - 19 Apr

Our top choices for Westchester hotels with a pool

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, (3,157 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 NZ$264
includes taxes & fees
12 Apr - 13 Apr
Aloft Chicago Mag Mile
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,782 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 NZ$401
includes taxes & fees
26 Apr - 27 Apr
The Wade
Indoor pool

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,716 reviews)
  • cleanliness
    Soak in relaxation at this historic Chicago hotel's indoor pool with spa amenities nearby.
The price is NZ$451
includes taxes & fees
11 Apr - 12 Apr
Hilton Chicago
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 NZ$395
includes taxes & fees
12 Apr - 13 Apr
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, (2,405 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is NZ$280
includes taxes & fees
12 Apr - 13 Apr
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,077 reviews)
  • cleanliness
    Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, spa pool haven, and 24-hour fitness centre.
The price is NZ$359
includes taxes & fees
26 Apr - 27 Apr
Hyatt Centric 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, (1,168 reviews)
The price is NZ$248
includes taxes & fees
26 Apr - 27 Apr
Homewood Suites by Hilton Chicago-Downtown
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,127 reviews)
  • cleanliness
    Indoor pool oasis at upscale Michigan Avenue aparthotel offers year-round swimming enjoyment.
The price is NZ$321
includes taxes & fees
14 Apr - 15 Apr
Sentral Michigan Avenue
Seasonal outdoor pool

Level Chicago - River North

Level Chicago - River North
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (923 reviews)
  • cleanliness
    Summer splashes and cityscape views await at this Chicago hotel's seasonal rooftop pool.
The price is NZ$390
includes taxes & fees
19 Apr - 20 Apr
Level Chicago - River North
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, (1,945 reviews)
  • cleanliness
    Dive into city centre luxury with a rejuvenating pool experience close to Chicago landmarks.
The price is NZ$278
includes taxes & fees
26 Apr - 27 Apr
Hilton Garden Inn Chicago Downtown South Loop
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
Spa pool

Top Westchester Hotel Reviews

Swissotel - Chicago

Swissotel - Chicago

10/10 Excellent
"Nice rooms, great view"
Irene 9-night trip
Posted 2 hours ago
Swissotel - Chicago

Frequently asked questions

What are some accommodation options with pools in Westchester?
Congress Plaza Hotel: Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. Hilton Chicago/Magnificent Mile Suites: Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool and flat-screen televisions. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 8-minute walk from Lake Michigan. Features a 24-hour fitness centre, an indoor pool and flat-screen televisions. Hotel Riu Plaza Chicago: 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, 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, United Center and Michigan Avenue. 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.