The Best Hotels with a Pool in Westchester, IL from ₩344,231 in 2026

Q: What are some accommodations with pools in Westchester?

Congress Plaza Hotel : Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool, and a sauna. Hotel Riu Plaza Chicago : Hotel, 3-minute walk from Michigan Avenue. Features a snack bar/deli, an indoor pool, and complimentary wireless internet access. The Chicago Hotel Collection - Magnificent Mile : Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. Hotel Felix River North/Magnificent Mile : Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool, and flat-screen televisions. River Hotel : Hotel, 5-minute walk from Michigan Avenue. Offers a rooftop terrace, a seasonal outdoor pool, and LED televisions.

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Our top choices for Westchester hotels with a pool

Palmer House a Hilton Hotel

Downtown Chicago

Dive into urban tranquility at the Palmer House pool, where historic charm meets modern luxury.

₩569,074 total

includes taxes & fees

Jun 21 - Jun 22

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.

₩403,420 total

includes taxes & fees

Jun 14 - Jun 15

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.

₩384,028 total

includes taxes & fees

Jun 14 - Jun 15

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.

₩502,574 total

includes taxes & fees

Jun 14 - Jun 15

The Hoxton Chicago

Downtown Chicago

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

₩526,734 total

includes taxes & fees

Jun 21 - Jun 22

Sheraton Grand Chicago Riverwalk

Downtown Chicago

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

₩643,640 total

includes taxes & fees

Jun 14 - Jun 15

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 center.

₩500,221 total

includes taxes & fees

Jun 14 - Jun 15

JW Marriott Chicago

Downtown Chicago

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

₩625,712 total

includes taxes & fees

Jun 12 - Jun 13

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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

10/10 Excellent

"Very helpful staff and friendly. Rooms were very clean and comfortable beds!"

Embassy Suites by Hilton Chicago Downtown River North

8/10 Good

"We enjoyed our room. The view in the corner room was beautiful and we were on the 11th floor. We did have a few minor issues like the room was not ready at 4, when we checked in, but the man at the counter was very kind and he did offer a different room. He also gave us a $10 off coupon for the restaurant and complimentary drinks. I wanted the corner view though, so we chose to wait until the room we reserved was ready. The sink in the bedroom never got hot water and at times, the water came out of the faucet brown. The bathroom water was fine though. Breakfast was great! All the staff and guests were wonderful. We met a housekeeper in the elevator during one of our trips out and she was so incredibly kind. We enjoyed our short visit with her. The location is also perfect! They offered in and out valet but we never took our car out, the location is so convenient. All in all, we would stay here again."

Congress Plaza Hotel

6/10 Okay

"Hotel is pretty "okay" if you are going for business, but our experience was not nice. The Air Conditioner wasn't working on a 65-80 degree outside, I told the front desk if they can help or make a room change but the solution was to give me a floor fan, not the type of help I was hoping and did not do anything to the A/C, it felt like "this is the best we can do, handle it". I've been in the hotel industry for 9 years and that's not how we handle thing. Bellmen and housekeepers were great and very committed to the service."

Frequently asked questions

What are some accommodations with pools in Westchester?

Congress Plaza Hotel: Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool, and a sauna. Hotel Riu Plaza Chicago: Hotel, 3-minute walk from Michigan Avenue. Features a snack bar/deli, an indoor pool, and complimentary wireless internet access. The Chicago Hotel Collection - Magnificent Mile: Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. Hotel Felix River North/Magnificent Mile: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool, and flat-screen televisions. River Hotel: Hotel, 5-minute walk from Michigan Avenue. Offers 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 like Wrigley Field, Navy Pier, 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'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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