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. Provides flat-screen televisions and an indoor pool. Omni Chicago Hotel : Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna. Hilton Chicago/Magnificent Mile Suites : Hotel, 3-minute walk from Millennium Park. Provides a full-service spa, an indoor pool, and a 24-hour fitness center. Hyatt Regency O'Hare Chicago : 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

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

World-class indoor pool in downtown offers lap swimming and family fun at this luxury hotel.

P21,650 total

includes taxes & fees

Jul 19 - Jul 20

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.

P17,067 total

includes taxes & fees

Jul 7 - Jul 8

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.

P13,000 total

includes taxes & fees

Jul 7 - Jul 8

Indoor pool, seasonal outdoor pool, free cabanas, sun loungers

Radisson Blu Aqua Hotel Chicago

Downtown Chicago

Luxurious indoor and seasonal outdoor pools form a relaxing oasis near Millennium Park and Michigan Avenue.

P18,624 total

includes taxes & fees

Jul 7 - Jul 8

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

P15,264 total

includes taxes & fees

Jul 9 - Jul 10

Indoor pool, open 6:00 AM to 10:00 PM, sun loungers

Sheraton Grand Chicago Riverwalk

Downtown Chicago

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

P20,752 total

includes taxes & fees

Jul 19 - Jul 20

JW Marriott Chicago

Downtown Chicago

Sleek indoor pool sanctuary opens onto Chicago adventures in this luxury retreat.

P25,488 total

includes taxes & fees

Aug 6 - Aug 7

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.

P14,534 total

includes taxes & fees

Jul 7 - Jul 8

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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

10/10 Excellent

"Very friendly and accommodating staff! Shuttle runs 24 hours. Highly recommend! Book your extended parking ahead of time."

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Stayed at the Magnificent Mile Suites for a couple get away. They offered valet parking for $82/night, $62/night self park. Used spothero to park a block and a half down for half the cost. BUT we did not have privileges to get the car whenever. Hotel does offer in/out privileges. We ubered and walked around the city. There are many forms of transportation to get around the city. Room was pretty clean, they offer a pool and fitness area. Overall good experience. Will stay again. "

Frequently asked questions

What are some accommodations with pools in Westchester?

Congress Plaza Hotel: Hotel, 2-minute walk from Michigan Avenue. Provides flat-screen televisions and an indoor pool. Omni Chicago Hotel: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna. Hilton Chicago/Magnificent Mile Suites: Hotel, 3-minute walk from Millennium Park. Provides a full-service spa, an indoor pool, and a 24-hour fitness center. Hyatt Regency O'Hare Chicago: 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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Our top choices for Westchester hotels with a pool

InterContinental Chicago Magnificent Mile by IHG