Westchester Hotel Guide - Hotels with Pool in Westchester, Chicago

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Check availability on Westchester Hotels with Pool

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct

Top Westchester Hotels with Pool

The Hoxton Chicago
Seasonal outdoor pool

The Hoxton Chicago

4.0 star property
9.0 out of 10, Wonderful, (1001)
"Great location, very clean, friendly staff!"
The price is €219
includes taxes & fees
26 Oct - 27 Oct
The Hoxton Chicago
Level Chicago Fulton Market
Executive lounge

Level Chicago Fulton Market

4.0 star property
9.2 out of 10, Wonderful, (312)
"Great place will return "
Level Chicago Fulton Market
Level Chicago – Old Town
Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (361)
"Great place to stay. Loved it!"
Level Chicago – Old Town
Sentral Michigan Avenue
Indoor pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (948)
"Great location and cleanliness of rooms. Staff was extremely helpful "
The price is €177
includes taxes & fees
6 Oct - 7 Oct
Sentral Michigan Avenue
Palmer House a Hilton Hotel
Indoor pool

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1997)
"Great property with great staff and amenities. "
The price is €195
includes taxes & fees
30 Oct - 31 Oct
Palmer House a Hilton Hotel
Best Western River North Hotel
Indoor pool

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1018)
"Great stay"
The price is €127
includes taxes & fees
2 Nov - 3 Nov
Best Western River North Hotel
Hyatt House Chicago West Loop
Indoor pool

Hyatt House Chicago West Loop

3.5 star property
8.8 out of 10, Excellent, (1045)
"Great location near lots of restaurants. "
The price is €195
includes taxes & fees
26 Oct - 27 Oct
Hyatt House Chicago West Loop
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2077)
"Great hotel"
The price is €159
includes taxes & fees
2 Nov - 3 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Hyatt Centric Chicago Magnificent Mile
Indoor pool

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1031)
"Great place to stay"
The price is €211
includes taxes & fees
30 Oct - 31 Oct
Hyatt Centric Chicago Magnificent Mile
Viceroy Chicago
Seasonal outdoor pool, open 8:00 AM to 5:00 PM, pool loungers

Viceroy Chicago

4.5 star property
9.4 out of 10, Exceptional, (1109)
"Hotel and staff were very pleasant "
The price is €330
includes taxes & fees
2 Nov - 3 Nov
Viceroy Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Westchester Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"The room & the view was amazing! The room was so big that it felt like the tv was across the room from the bed. The location was ideal for what we came to Chicago for. I would definitely stay here again. Clean. Spacious. Comfort. Quiet. Gorgeous view. Location. In room amenities. All 10/10! "
Nichole 1-night trip
Posted 2 days ago
Congress Plaza Hotel

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Frequently asked questions

What are some accommodation options with pools in Westchester?
Congress Plaza Hotel: Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool and flat-screen televisions. Freehand Chicago: Hotel, 4-minute walk from Michigan Avenue. Offers complimentary high-speed (wired) Internet access, an indoor pool and LCD televisions. Embassy Suites by Hilton Chicago Downtown River North: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool and a steam room. Hilton Chicago/Magnificent Mile Suites: Hotel steps from State Street. Offers a full-service spa, an indoor pool and a 24-hour fitness centre. Hilton Garden Inn Chicago Downtown/Magnificent Mile: Hotel, 8-minute walk from Lake Michigan. Features a 24-hour fitness centre, an indoor pool and flat-screen televisions.
What is there to see and do in Westchester?
While you're in the area, consider exploring places such as Wrigley Field, Michigan Avenue and Navy Pier. 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.