Find Hotels with a Pool in Westchester, IL

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Top Westchester Hotels with a Pool

Frequently asked questions

What are some accommodations with pools in Westchester?
Congress Plaza Hotel: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a steam room. InterContinental Chicago Magnificent Mile by IHG: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool, and flat-screen televisions. Hilton Chicago/Magnificent Mile Suites: Hotel, 8-minute walk from Lake Michigan. Features a 24-hour fitness center, an indoor pool, and flat-screen televisions. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 5-minute walk from Michigan Avenue. Features buffet, an indoor pool, and LCD televisions. Crowne Plaza Chicago West Loop by IHG: Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool, and complimentary wireless internet access.
What is there to see and do in Westchester?
While you're in the area, consider exploring places like Wrigley Field, Michigan Avenue, and Navy Pier. 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.