🏊 Top 10 Westchester Hotels with Swimming Pool

Q: 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, 4-minute walk from State Street. Features 2 restaurants, an indoor pool and a health club. Hilton Chicago/Magnificent Mile Suites : Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool and complimentary wireless Internet access. Eurostars Magnificent Mile : Hotel, 5-minute walk from Michigan Avenue. Features a rooftop terrace, a seasonal outdoor pool and LED televisions.

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Our top choices for Westchester hotels with a pool

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

RM479 total

includes taxes & fees

19 Mar - 20 Mar

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

Aloft Chicago Mag Mile

Downtown Chicago

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

RM459 total

includes taxes & fees

5 Mar - 6 Mar

The Wade

Downtown Chicago

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

RM505 total

includes taxes & fees

22 Mar - 23 Mar

Homewood Suites by Hilton Chicago-Downtown

Downtown Chicago

RM531 total

includes taxes & fees

22 Mar - 23 Mar

The Hoxton Chicago

Downtown Chicago

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

RM820 total

includes taxes & fees

8 Mar - 9 Mar

Outdoor pool, 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.

RM507 total

includes taxes & fees

8 Mar - 9 Mar

Level Chicago - River North

Downtown Chicago

Summer splashes and cityscape views await at this Chicago hotel's seasonal rooftop pool.

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Dive into city centre luxury with a rejuvenating pool experience close to Chicago landmarks.

RM547 total

includes taxes & fees

18 Mar - 19 Mar

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Choose what matters most at hotels with a pool in Westchester

Breakfast included

Hot tub

Top Westchester Hotel Reviews

Congress Plaza Hotel

10/10 Excellent

"Very pleased with our room; very clean, obviously "moderned" up a little for an old hotel. Main lobby beaytufu"

The Royal Sonesta Chicago Downtown

10/10 Excellent

"My wife and I agreed that this was the nicest room we've ever stayed in, and we've stayed in a lot of nice rooms. Do not even hesitate to stay here and please do yourself a favor and splurge on a State Suite like we did. Maybe we got lucky with the room we ended up in, but we LOVED staring at the river and cityscape among the Chicago skyscrapers for a week -- and I can't even begin to describe the luxury level on the bathroom and supersize tub. Stay here. Do it. You deserve it."

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, 4-minute walk from State Street. Features 2 restaurants, an indoor pool and a health club. Hilton Chicago/Magnificent Mile Suites: Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool and complimentary wireless Internet access. Eurostars Magnificent Mile: Hotel, 5-minute walk from Michigan Avenue. Features a rooftop terrace, a seasonal outdoor pool and LED televisions.

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.

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Treat yourself

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Check availability on Westchester Hotels with Swimming Pools

Our top choices for Westchester hotels with a pool

Hilton Chicago/Magnificent Mile Suites

Aloft Chicago Mag Mile

The Wade

Homewood Suites by Hilton Chicago-Downtown

The Hoxton Chicago

DoubleTree by Hilton Chicago - Magnificent Mile

Level Chicago - River North

Hilton Garden Inn Chicago Downtown South Loop

Embassy Suites by Hilton Chicago Downtown River North

Sentral Michigan Avenue

Choose what matters most at hotels with a pool in Westchester

Top Westchester Hotel Reviews

Congress Plaza Hotel

Hilton Chicago/Magnificent Mile Suites

Embassy Suites by Hilton Chicago Downtown River North

Courtyard by Marriott Chicago Magnificent Mile

Palmer House a Hilton Hotel

Hilton Chicago

Eurostars Magnificent Mile

Hyatt Regency Chicago

The Royal Sonesta Chicago Downtown

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