Hotels with Swimming Pool, Westchester Chicago

Q: What are some accommodations 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 center, 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.

Schiller Woods view in Chicago of Illinois

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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.

P11,951 total

includes taxes & fees

Apr 27 - Apr 28

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

Aloft 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.

P8,557 total

includes taxes & fees

Apr 12 - Apr 13

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

P9,693 total

includes taxes & fees

Apr 12 - Apr 13

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.

P9,042 total

includes taxes & fees

Apr 12 - Apr 13

Renaissance Chicago Downtown Hotel

Downtown Chicago

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

P15,878 total

includes taxes & fees

Apr 11 - Apr 12

The Hoxton Chicago

Downtown Chicago

Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.

P12,522 total

includes taxes & fees

Apr 12 - Apr 13

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Chicago hotel offers refreshing stays with indoor pool, fitness center, and walkable Michigan Avenue access.

P10,810 total

includes taxes & fees

Apr 12 - Apr 13

Sheraton Grand Chicago Riverwalk

Downtown Chicago

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

P16,207 total

includes taxes & fees

Apr 10 - Apr 11

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Choose what matters most at hotels with a pool in Westchester

Breakfast included

Hot tub

Top Westchester Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"The hotel is perfect. The view was beautiful. Room was clean, staff were professional and friendly. The food and drinks was amazing 😋 😍 "

Hilton Chicago

6/10 Okay

"Didn't get the room I reserved (2 months ago), which was 2 double beds. Instead gave me a king (for 2 adults and a child). What's the point of a reservation if they're just going to give my room away? Easter weekend, hotel full of young teenage girls, who instead of acting like young ladies, were running up and down the hallways like 6 year old boys, and throwing ice at each other until I had to call security."

Frequently asked questions

What are some accommodations 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 center, 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 like 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'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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