Westchester Hotels with Pool, Chicago: Westchester Hotel Guide

Q: What are some accommodation options with pools in Westchester?

Congress Plaza Hotel : Hotel, 2-minute walk from Michigan Avenue. Provides flat-screen televisions and an indoor pool. Omni Chicago Hotel : Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool and a sauna. Hilton Chicago/Magnificent Mile Suites : Hotel, 3-minute walk from Millennium Park. Provides a full-service spa, an indoor pool and a 24-hour fitness centre. Hyatt Regency O'Hare Chicago : Hotel, 3-minute walk from Merchandise Mart. Provides 2 restaurants, an indoor pool and a sauna.

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Our top choices for Westchester hotels with a pool

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Chicago hotel offers refreshing stays with indoor pool, fitness centre, and walkable Michigan Avenue access.

includes taxes & fees

6 Jul - 7 Jul

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

World-class indoor pool in city centre offers lap swimming and family fun at this luxury hotel.

includes taxes & fees

6 Jul - 7 Jul

Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers

Radisson Blu Aqua Hotel Chicago

Downtown Chicago

Luxurious indoor and seasonal outdoor pools form a relaxing oasis near Millennium Park and Michigan Avenue.

includes taxes & fees

6 Jul - 7 Jul

Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Splash into the city at this city centre hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.

includes taxes & fees

7 Jul - 8 Jul

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

includes taxes & fees

7 Jul - 8 Jul

JW Marriott Chicago

Downtown Chicago

Sleek indoor pool sanctuary opens onto Chicago adventures in this luxury retreat.

includes taxes & fees

10 Jul - 11 Jul

Outdoor pool, 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.

includes taxes & fees

6 Jul - 7 Jul

Sheraton Grand Chicago Riverwalk

Downtown Chicago

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

includes taxes & fees

19 Jul - 20 Jul

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Breakfast included

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Top Westchester Hotel Reviews

Hyatt Regency O'Hare Chicago

10/10 Excellent

"The Hyatt truly creates a euphoric feeling of a staycation and vacation wherever you are. They are gold standard and I can’t wait to come back to one of the properties."

Frequently asked questions

What are some accommodation options with pools in Westchester?

Congress Plaza Hotel: Hotel, 2-minute walk from Michigan Avenue. Provides flat-screen televisions and an indoor pool. Omni Chicago Hotel: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool and a sauna. Hilton Chicago/Magnificent Mile Suites: Hotel, 3-minute walk from Millennium Park. Provides a full-service spa, an indoor pool and a 24-hour fitness centre. Hyatt Regency O'Hare Chicago: Hotel, 3-minute walk from Merchandise Mart. 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 such as 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 plan to visit Westchester in the hottest months of July, August or June, when the average temp is 22°C. Accommodation 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 -1°C.

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Our top choices for Westchester hotels with a pool

Embassy Suites by Hilton Chicago Downtown Magnificent Mile