Find Hotels with a Pool in Westchester, IL from CA $165

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Check availability on Westchester Hotels with a Pool

Our top choices for Westchester hotels with a pool

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,927 reviews)
The price is CA $142
CA $167 total
includes taxes & fees
Mar 23 - Mar 24
Hilton Chicago/Magnificent Mile Suites

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,724 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 CA $177
CA $208 total
includes taxes & fees
Mar 31 - Apr 1
The Wade

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,147 reviews)
  • cleanliness
    Splash into the city at this downtown hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.
The price is CA $148
CA $174 total
includes taxes & fees
Mar 22 - Mar 23
Aloft Chicago Mag Mile

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.
The price is CA $188
CA $262 total
includes taxes & fees
Mar 22 - Mar 23
The Hoxton Chicago

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Splash into pure relaxation at this downtown hotel's indoor pool with loungers and fitness centre access.
The price is CA $262
CA $349 total
includes taxes & fees
Mar 21 - Mar 22
Renaissance Chicago Downtown Hotel

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,356 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is CA $156
CA $184 total
includes taxes & fees
Mar 23 - Mar 24
DoubleTree by Hilton Chicago - Magnificent Mile

Level Chicago - River North

Level Chicago - River North
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (882 reviews)
  • cleanliness
    Summer splashes and cityscape views await at this Chicago hotel's seasonal rooftop pool.
The price is CA $188
CA $254 total
includes taxes & fees
Mar 22 - Mar 23
Level Chicago - River North

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,090 reviews)
  • cleanliness
    Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, hot tub haven, and 24-hour fitness centre.
The price is CA $176
CA $246 total
includes taxes & fees
Apr 2 - Apr 3
Hyatt Centric Chicago 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, (4,394 reviews)
  • cleanliness
    Make a splash at this downtown Chicago hotel with an indoor pool, fitness centre, and stunning city views from each room.
The price is CA $140
CA $165 total
includes taxes & fees
Mar 24 - Mar 25
Hilton Garden Inn 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, (2,807 reviews)
  • cleanliness
    Chicago hotel offers refreshing stays with indoor pool, fitness centre, and walkable Michigan Avenue access.
The price is CA $146
CA $212 total
includes taxes & fees
Apr 6 - Apr 7
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.

Choose what matters most at hotels with a pool in Westchester

Top Westchester Hotel Reviews

Frequently asked questions

What are some accommodations 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, 12-minute walk from Millennium Park. Offers 2 restaurants, an indoor pool, and a health club. Hilton Chicago/Magnificent Mile Suites: Hotel, 3-minute walk from Michigan Avenue. Provides a snack bar/deli, an indoor pool, and complimentary wireless internet access. Hilton Chicago O'Hare Airport: Hotel, 8-minute walk from Lake Michigan. Offers a 24-hour fitness center, an indoor pool, and flat-screen televisions.
What is there to see and do in Westchester?
While you're in the area, consider exploring places like 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're planning to visit Westchester in the hottest months of July, August, or June when the average temp is 71°F. Lodging 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 31°F.

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