The Best Hotels with a Pool in Westchester, IL from ￥27,809 in 2026

Q: What are some accommodations with pools in Westchester?

Congress Plaza Hotel : Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. The Chicago Hotel Collection - Magnificent Mile : Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Hyatt Regency O'Hare Chicago : Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool, and a sauna. The Chicago Hotel Collection Ambassador Gold Coast : Hotel, 4-minute walk from State Street. Provides 2 restaurants, an indoor pool, and a health club. Hilton Chicago/Magnificent Mile Suites : Hotel located near Donald E. Stephens Convention Center. Features 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

￥28,165 total

includes taxes & fees

Jul 5 - Jul 6

The Wade

Downtown Chicago

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

￥30,807 total

includes taxes & fees

Jun 28 - Jun 29

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.

￥42,594 total

includes taxes & fees

Jun 30 - Jul 1

Sheraton Grand Chicago Riverwalk

Downtown Chicago

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

￥47,753 total

includes taxes & fees

Jul 5 - Jul 6

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

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

￥30,508 total

includes taxes & fees

Jul 2 - Jul 3

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.

￥32,218 total

includes taxes & fees

Jul 5 - Jul 6

Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Dive into modern bliss at this downtown hotel, where the indoor pool sparkles alongside skyline views.

￥27,809 total

includes taxes & fees

Jul 5 - Jul 6

Renaissance Chicago Downtown Hotel

Downtown Chicago

Splash into pure relaxation at this downtown hotel's indoor pool with loungers and fitness center access.

￥49,670 total

includes taxes & fees

Jul 2 - Jul 3

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Choose what matters most at hotels with a pool in Westchester

Breakfast included

Hot tub

Top Westchester Hotel Reviews

Omni Chicago Hotel

10/10 Excellent

"We had a wonderful stay. The staff were attentive and our room was spacious."

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"The location is fantastic, and the hotel is high quality. My room was very good, although I expected a bit more from this hotel as it seemed a bit outdated (not horrible, or in big need of a renovation, but some minor improvments would go a long way)."

Hotel Felix River North/Magnificent Mile

8/10 Good

"It was sufficient. It felt clean, but it did not feel luxurious. The main benefit came from the location. Walkability is high. It was bare-bones. The soap dispenser didn’t have enough for a two night stay. Tv was hard to use. If you are out exploring the city, this hotel is fine. If you are basing your experience on the hotel itself (like a staycation), I think you will be disappointed."

Hyatt Regency Chicago

10/10 Excellent

"Our room was very clean and we especially liked the cooling system options which were so user friendly. We loved the lobby openness, decor and all the choices. Wished fresh coffee was offered complimentary. The coffee pods in the room were not tasty. Other than that we were very pleased and would come again."

Frequently asked questions

What are some accommodations with pools in Westchester?

Congress Plaza Hotel: Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. The Chicago Hotel Collection - Magnificent Mile: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Hyatt Regency O'Hare Chicago: Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool, and a sauna. The Chicago Hotel Collection Ambassador Gold Coast: Hotel, 4-minute walk from State Street. Provides 2 restaurants, an indoor pool, and a health club. Hilton Chicago/Magnificent Mile Suites: Hotel located near Donald E. Stephens Convention Center. Features 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 like 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'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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