The Best Hotels with a Pool in Westchester, IL from AED 651 in 2026 | Expedia

A calm lake with ducks, autumn trees, and a grassy park area.

A calm lake with ducks, autumn trees, and a grassy park area.

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Check availability on Westchester Hotels with a Pool

Tonight

28 Jun - 29 Jun

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29 Jun - 30 Jun

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In two weeks

10 Jul - 12 Jul

Our top choices for Westchester hotels with a pool

Indoor pool

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

AED 674 total

includes taxes & fees

5 Jul - 6 Jul

Indoor pool

The Wade

Downtown Chicago

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

AED 738 total

includes taxes & fees

1 Jul - 2 Jul

Indoor pool

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.

AED 970 total

includes taxes & fees

30 Jun - 1 Jul

Indoor pool, open 6:00 AM to 10:00 PM, sun loungers

Sheraton Grand Chicago Riverwalk

Downtown Chicago

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

AED 1,087 total

includes taxes & fees

5 Jul - 6 Jul

Indoor pool

Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

AED 721 total

includes taxes & fees

6 Jul - 7 Jul

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.

AED 651 total

includes taxes & fees

2 Jul - 3 Jul

Seasonal outdoor pool

The Hoxton, Chicago

Downtown Chicago

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

AED 1,152 total

includes taxes & fees

1 Jul - 2 Jul

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.

AED 1,105 total

includes taxes & fees

6 Jul - 7 Jul

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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/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Great place to stay....."

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

10/10 Excellent

"Great stay overall! I really liked the open bar, and it was a nice bonus that we could request coffee, tea, and other beverages anytime during the day. Shoutout to Giselle for making our coffee perfectly late night! The daily fruit selection was also a nice touch. We had a little trouble with the Chromecast, but it wasn't a big issue since we ended up watching the live TV channels instead. Tip: There isn't complimentary bottled water in the room, but there is a water station in the lobby. Just bring a reusable bottle or container to refill throughout your stay. Also, if you need housekeeping, be sure to call and request it, as they don't automatically clean your room each day. Overall, we had a great stay. The hotel is in a fantastic location—within walking distance of major landmarks, with a pharmacy and grocery store nearby for added convenience. We'll definitely stay here again the next time we return to Chicago!"

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

8/10 Good

"This is an old school Chicago hotel with charm. The room was very clean and the staff was very nice and accommodating. Keenan the Bellman, was a great help! He loaned us umbrellas for our walk around, and suggested great places to eat! Great employee for the hotel! The location is excellent and in a safe area! I’ve stayed at this hotel 3-4 times through the years of business travel and it has never disappointed."

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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. Hilton Chicago/Magnificent Mile Suites: Hotel steps from State Street. Features a full-service spa, an indoor pool, and a 24-hour fitness center. The Chicago Hotel Collection - Magnificent Mile: Hotel steps from Michigan Avenue. Provides 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 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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