Book the Best Hotels with POOL in Westchester in 2026

Q: What are some accommodations with pools in Westchester?

Congress Plaza Hotel : Hotel, 3-minute walk from Merchandise Mart. Provides 2 restaurants, an indoor pool, and a sauna. The Chicago Hotel Collection Ambassador Gold Coast : Hotel steps from 875 North Michigan Avenue. Features flat-screen televisions and an indoor pool. Hyatt Regency O'Hare Chicago : Hotel, 10-minute walk from University of Illinois Chicago. Offers a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access. Omni Chicago Hotel : Hotel steps from Michigan Avenue. Features 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

1. Hyatt Lodge Oak Brook Chicago

Oak Brook

Discover serene luxury at this lakeside hotel where an indoor pool sanctuary awaits, surrounded by lush forests and hiking trails.

CA $328 total

includes taxes & fees

Aug 9 - Aug 10

Indoor pool, open 8:00 AM to 11:00 PM, sun loungers

2. Holiday Inn Express & Suites Bensenville - O'Hare by IHG

Bensenville

Splash into relaxation at this airport hotel with an indoor pool and comfy sun loungers.

CA $224 total

includes taxes & fees

Aug 23 - Aug 24

3. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

Splash into cool escape at Chicago O'Hare's serene indoor pool, perfect for year-round laps and leisure dips.

CA $208 total

includes taxes & fees

Aug 24 - Aug 25

4. Springhill Suites by Marriott Chicago Elmhurst/Oakbrook Area

Elmhurst

Dive into the hotel's all-season indoor pool with refreshing aquatic amenities, just steps from Fashion Outlets of Chicago.

CA $181 total

includes taxes & fees

Aug 23 - Aug 24

5. Hyatt Place Chicago Midway Airport

Bedford Park

Sun-drenched afternoons await at this indoor pool retreat with refreshing amenities and comfort.

CA $267 total

includes taxes & fees

Sep 2 - Sep 3

6. Hampton Inn & Suites Downers Grove Chicago

Downers Grove

Enjoy a refreshing pool escape at this Chicago-area hotel, where the indoor aquatic retreat complements stylish accommodations.

CA $204 total

includes taxes & fees

Aug 24 - Aug 25

7. Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Bensenville

Relax and revive with year-round swims at this O'Hare hotel's indoor pool and hot tub retreat.

CA $174 total

includes taxes & fees

Aug 24 - Aug 25

8. Embassy Suites by Hilton Chicago O'Hare Rosemont

Rosemont

Serene indoor pool with adult supervision provides family-friendly escape at this upscale hotel.

CA $248 total

includes taxes & fees

Aug 31 - Sep 1

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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 McCormick Place Chicago

10/10 Excellent

"I wish they had a vending machine on our floor with snacks"

Omni Chicago Hotel

10/10 Excellent

"Location was great! Right on Michigan Ave, close to lots of stores. Definitely recommend Beatrix restaurant the next block over for breakfast/brunch. It was fantastic. Bar and restaurant on site at hotel were also good. We had a pizza and salad with grilled salmon. Speciality drinks were amazing! Staff was extremely nice. Everyone smiled and greeted us everywhere we went in the hotel. Definitely recommend."

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent

"i had to best time being in chicago thanks to crowne plaza! there was a gentleman at the counter who was very very helpful & super sweet! they are on top of cleanliness as well. my first time ever staying in a hotel by myself & the experience was all around amazing."

Frequently asked questions

What are some accommodations with pools in Westchester?

Congress Plaza Hotel: Hotel, 3-minute walk from Merchandise Mart. Provides 2 restaurants, an indoor pool, and a sauna. The Chicago Hotel Collection Ambassador Gold Coast: Hotel steps from 875 North Michigan Avenue. Features flat-screen televisions and an indoor pool. Hyatt Regency O'Hare Chicago: Hotel, 10-minute walk from University of Illinois Chicago. Offers a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access. Omni Chicago Hotel: Hotel steps from Michigan Avenue. Features 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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