TOP Hotels with Pool in Westchester, IL for 2026

Q: What are some accommodation options with pools in Westchester?

Congress Plaza Hotel : Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool and a sauna. The Chicago Hotel Collection - Magnificent Mile : Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. Hyatt Regency O'Hare Chicago : Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool and a sauna. Hilton Chicago O'Hare Airport : Hotel located near Donald E. Stephens Convention Center. Offers an indoor pool, an outdoor pool and a snack bar/deli.

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Our top choices for Westchester hotels with a pool

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

฿6,056 total

includes taxes & fees

5 Jul - 6 Jul

Sheraton Grand Chicago Riverwalk

Downtown Chicago

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

฿8,920 total

includes taxes & fees

5 Jul - 6 Jul

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

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

฿6,031 total

includes taxes & fees

5 Jul - 6 Jul

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

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

฿8,687 total

includes taxes & fees

1 Jul - 2 Jul

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

Aloft by Marriott 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.

฿5,838 total

includes taxes & fees

2 Jul - 3 Jul

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.

฿6,670 total

includes taxes & fees

7 Jul - 8 Jul

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

Radisson Blu Aqua Hotel Chicago

Downtown Chicago

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

฿8,805 total

includes taxes & fees

1 Jul - 2 Jul

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 centre.

฿8,596 total

includes taxes & fees

30 Jun - 1 Jul

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Choose what matters most at hotels with a pool in Westchester

Breakfast included

Hot tub

Top Westchester Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

8/10 Good

"Location in West Loop is fantastic, a block away from Whole Foods and a number of great restaurants in Greek town. The staff was fantastic in addressing our needs immediately including a clogged sink and sliding door that came off the tracks. The infrastructure is a bit old and outdated. The only complaint was that we had requested a crib, which the check-in staff had reassured us would be in our room. However, it was not there when we arrived. We called to ask for one to be brought up, which took about 20 minutes. Normally, it would not be a big deal, but we arrived at 11 PM, so it was less than ideal for our toddler as it was very much past his bedtime."

Hilton Chicago O'Hare Airport

10/10 Excellent

"I really can't write a comprehensive review because we only stayed here for a short layover. Arrived at midnight and left at 5:30. I can, however, say that the hotel was clean, check-in was efficient and location was great as we were able to walk from our plane to the hotel in under 10 minutes. Just what we were looking for. Of course, I wish the price was less especially since we were only there for 5 hours, but it met our needs and we were able to rest for a little while before making our connection. I wish all airports had this convenient hotel choice on site."

Frequently asked questions

What are some accommodation options with pools in Westchester?

Congress Plaza Hotel: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool and a sauna. The Chicago Hotel Collection - Magnificent Mile: Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. Hyatt Regency O'Hare Chicago: Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool and a sauna. Hilton Chicago O'Hare Airport: Hotel located near Donald E. Stephens Convention Center. Offers an indoor pool, an outdoor pool and a snack bar/deli.

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 Soldier Field. 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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