Hotels with Swimming Pool, Westchester Chicago

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.

P15,336 total

includes taxes & fees

May 25 - May 26

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.

P10,200 total

includes taxes & fees

May 25 - May 26

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

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

P11,656 total

includes taxes & fees

May 26 - May 27

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.

P14,896 total

includes taxes & fees

May 27 - May 28

The Wade

Downtown Chicago

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

P12,400 total

includes taxes & fees

May 26 - May 27

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.

P11,844 total

includes taxes & fees

May 26 - May 27

Sheraton Grand Chicago Riverwalk

Downtown Chicago

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

P18,645 total

includes taxes & fees

May 26 - May 27

The Royal Sonesta Chicago River North

Downtown Chicago

Stylish indoor pool retreat in downtown Chicago makes luxury laps a breeze after sightseeing.

P16,577 total

includes taxes & fees

May 26 - May 27

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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

"Nice clean hotel downtown."

Holiday Inn Chicago Dwtn - The Mart by IHG

6/10 Okay

"The location is very good, but the hotel needs to make some improvements. First, when you enter, there is a strong smell of humidity, which I imagine is coming from the carpet. The same smell was noticeable in the hallways and in the room. In the room, I found that the sink was clogged, and the shower curtain had a strong marijuana smell. I believe housekeeping should use a checklist before leaving the room so the next guest can have a better impression. Other than that, everything was good!"

Hotel Felix River North/Magnificent Mile

10/10 Excellent

"Stayed here many times over the years. Good value, great location. Rooms are small but efficient and clean with very comfy beds. Quiet, good shades. My only request would be to PLEASE INSTALL ADEQUATELY LONG SHOWER CURTAINS SO WE ARENT CONSTANTLY FLOODING THE BATHROOM FLOOR."

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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