The Best Hotels with a Pool in Westchester, IL from ₩293,173 in 2026

Q: What are some accommodations with pools in Westchester?

The Chicago Hotel Collection Ambassador Gold Coast : Hotel steps from 875 North Michigan Avenue. Features flat-screen televisions and an indoor pool. Omni Chicago Hotel : Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel : Hotel, 3-minute walk from Millennium Park. Offers a full-service spa, an indoor pool, and a 24-hour fitness center. Hyatt Regency O'Hare Chicago : Hotel, 10-minute walk from University of Illinois Chicago. Features a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access. Hilton Chicago O'Hare Airport : Hotel, 3-minute walk from Merchandise Mart. Provides 2 restaurants, an indoor pool, and a sauna.

A calm lake with ducks, autumn trees, and a grassy park area.

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Our top choices for Westchester hotels with a pool

The Wade

Downtown Chicago

Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.

₩301,156 total

includes taxes & fees

Jul 19 - Jul 20

Palmer House a Hilton Hotel

Downtown Chicago

Dive into urban tranquility at the Palmer House pool, where historic charm meets modern luxury.

₩515,008 total

includes taxes & fees

Aug 9 - Aug 10

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, hot tub haven, and 24-hour fitness center.

₩384,564 total

includes taxes & fees

Jul 19 - Jul 20

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

₩375,714 total

includes taxes & fees

Aug 9 - Aug 10

Indoor pool, open 7:00 AM to 10:00 PM, sun loungers

Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Splash into the city at this downtown hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.

₩335,813 total

includes taxes & fees

Aug 9 - Aug 10

Outdoor pool, cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.

₩347,774 total

includes taxes & fees

Aug 10 - Aug 11

Renaissance Chicago Downtown Hotel

Downtown Chicago

Splash into pure relaxation at this downtown hotel's indoor pool with loungers and fitness center access.

₩468,711 total

includes taxes & fees

Aug 9 - Aug 10

Sheraton Grand Chicago Riverwalk

Downtown Chicago

Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.

₩532,820 total

includes taxes & fees

Jul 19 - Jul 20

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Choose what matters most at hotels with a pool in Westchester

Breakfast included

Hot tub

Top Westchester Hotel Reviews

Hyatt Regency O'Hare Chicago

8/10 Good

"Dated but comfortable and had all amenities"

Frequently asked questions

What are some accommodations with pools in Westchester?

The Chicago Hotel Collection Ambassador Gold Coast: Hotel steps from 875 North Michigan Avenue. Features flat-screen televisions and an indoor pool. Omni Chicago Hotel: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel: Hotel, 3-minute walk from Millennium Park. Offers a full-service spa, an indoor pool, and a 24-hour fitness center. Hyatt Regency O'Hare Chicago: Hotel, 10-minute walk from University of Illinois Chicago. Features a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access. Hilton Chicago O'Hare Airport: Hotel, 3-minute walk from Merchandise Mart. Provides 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 like United Center, Wrigley Field, 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'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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