The Best Hotels with a Pool in Westchester, IL from ￥20,271 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.

￥36,689 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.

￥25,171 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.

￥23,396 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.

￥20,271 total

includes taxes & fees

Aug 31 - Sep 1

5. Hyatt Place Chicago Midway Airport

Bedford Park

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

￥30,021 total

includes taxes & fees

Sep 1 - Sep 2

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.

￥22,927 total

includes taxes & fees

Aug 13 - Aug 14

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.

￥19,212 total

includes taxes & fees

Sep 1 - Sep 2

8. Embassy Suites by Hilton Chicago O'Hare Rosemont

Rosemont

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

￥31,261 total

includes taxes & fees

Aug 30 - Aug 31

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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

"Great place and location"

The Chicago Hotel Collection - Magnificent Mile

8/10 Good

"First, I’m going to say that price and location wise: it’ll be my go-to place in Chicago. I really enjoyed the room and was impressed by the view we got. As someone who’s frequently made trips to Chicago, it felt like Chicago to me. And the pizza, bagel and ice cream right next door was a bonus. What I found frustrating was that the texting line didn’t work. I had to call because I could not get answers via the text service they kept promoting. Also, the upgraded package, which apparently was for everyone, was not well explained. For example, I was traveling with a child, and they didn’t tell me that they would be counted for breakfast despite them only being part of the whip cream club, I wasn’t told that the drink tickets and the $10 dinner was available at any time on weekends, despite a time limit posted on the website. I found out by eavesdropping that the TV actually worked and that the internet was easy to access. But, the staff, as people, seemed really kind. They just don’t seem like they communicate well with each other as my card wasn’t working despite having called. They seemed extremely hard working. And, I’ll say it again - for the price and the location - I will stay there again."

The Royal Sonesta Chicago Downtown

10/10 Excellent

"The room was clean and the perfect location to watch the river get dyed. Because we were there for St Patricks Day, the elevators were a huge problem to get down from our room so ended up taking the stairs. This is not the hotels fault by any means. There is a small restaurant and bar. We only got drinks from there. The decor was great and we were so comfy in our bed. I would definitely stay here again!!"

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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