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Our top choices for Westchester hotels with a pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,775 reviews)
  • cleanliness
    Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.
The price is Rp2.869.620
Rp3.369.002 total
includes taxes & fees
27 Apr - 28 Apr
The Wade

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,161 reviews)
  • cleanliness
    Splash into the city at this city centre hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.
The price is Rp2.054.580
Rp2.412.179 total
includes taxes & fees
12 Apr - 13 Apr
Aloft Chicago Mag Mile

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,055 reviews)
The price is Rp2.327.618
Rp2.732.391 total
includes taxes & fees
12 Apr - 13 Apr
Hilton Chicago/Magnificent Mile Suites

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,399 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is Rp2.171.402
Rp2.549.009 total
includes taxes & fees
12 Apr - 13 Apr
DoubleTree by Hilton Chicago - Magnificent Mile

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Splash into pure relaxation at this city centre hotel's indoor pool with loungers and fitness centre access.
The price is Rp3.243.180
Rp4.316.568 total
includes taxes & fees
10 Apr - 11 Apr
Renaissance Chicago Downtown Hotel

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,005 reviews)
  • cleanliness
    Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.
The price is Rp2.582.658
Rp3.530.315 total
includes taxes & fees
12 Apr - 13 Apr
The Hoxton Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2,804 reviews)
  • cleanliness
    Chicago hotel offers refreshing stays with indoor pool, fitness centre, and walkable Michigan Avenue access.
The price is Rp1.888.176
Rp2.714.892 total
includes taxes & fees
12 Apr - 13 Apr
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,617 reviews)
  • cleanliness
    Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.
The price is Rp3.548.820
Rp4.763.996 total
includes taxes & fees
26 Apr - 27 Apr
Sheraton Grand Chicago Riverwalk

Homewood Suites by Hilton Chicago-Downtown

Homewood Suites by Hilton Chicago-Downtown
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,158 reviews)
The price is Rp2.078.861
Rp2.440.376 total
includes taxes & fees
26 Apr - 27 Apr
Homewood Suites by Hilton Chicago-Downtown

Level Chicago - River North

Level Chicago - River North
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (913 reviews)
  • cleanliness
    Summer splashes and cityscape views await at this Chicago hotel's seasonal rooftop pool.
The price is Rp2.721.385
Rp3.613.514 total
includes taxes & fees
6 Apr - 7 Apr
Level Chicago - River North
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.

Choose what matters most at hotels with a pool in Westchester

Top Westchester Hotel Reviews

Frequently asked questions

What are some accommodation options 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, 4-minute walk from Michigan Avenue. Provides full, an indoor pool and flat-screen televisions. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 8-minute walk from Lake Michigan. Features a 24-hour fitness centre, an indoor pool and flat-screen televisions. Hotel Riu Plaza Chicago: Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool and complimentary wireless Internet access. Hilton Chicago O'Hare Airport: Hotel, 12-minute walk from Millennium Park. Features 2 restaurants, an indoor pool and a health club.
What is there to see and do in Westchester?
While you're in the area, consider exploring places such as Wrigley Field, United Center 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.