Hotels with Swimming Pool in Westchester, Chicago

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Check availability on Westchester Hotels with Swimming Pool

Top Westchester Hotels with Swimming Pool

The Hoxton Chicago
Relax by the rooftop pool with a stunning city view, surrounded by comfortable lounge chairs and a small table.

The Hoxton Chicago

4.0 star property
9.0 out of 10, Wonderful, (1012)
"Awesome staff. The
pool
was great. Loved The Lazy Bird."
Jennifer
The price is P11,241
P13,195 total
includes taxes & fees
Aug 10 - Aug 11
The Hoxton Chicago
Best Western River North Hotel
Relax by the rectangular pool surrounded by lounge chairs and umbrellas.

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1014)
"Property was clean and secure. Rooms were clean.
Pool
area was family welcoming my kids had a nice time."
Patricia
The price is P7,059
P8,287 total
includes taxes & fees
Jul 27 - Jul 28
Best Western River North Hotel
Hyatt Centric Chicago Magnificent Mile
Indoor pool

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1029)
"Great, friendly staff the updated rooms & the
pool
/whirlpool were top notch. Exceptional value and would highly recommend it to families/others looking for a good Chicago “tourist-friendly”, but high quality hotel. "
Nicholas
The price is P9,555
P12,874 total
includes taxes & fees
Jul 27 - Jul 28
Hyatt Centric Chicago Magnificent Mile
Palmer House a Hilton Hotel
Relax by the pool surrounded by comfortable lounge chairs and framed artwork.

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very Good, (1784)
"Socializing with a glass of wine in the bar areas was a high priced luxury!
Pool
was wonderful, room was comfortable and staff were outstanding. "
Clarke
The price is P10,275
P13,474 total
includes taxes & fees
Aug 4 - Aug 5
Palmer House a Hilton Hotel
Level Chicago Fulton Market
Enjoy a modern dining experience with a long table, blue chairs, and a unique pendant light.

Level Chicago Fulton Market

4.0 star property
9.2 out of 10, Wonderful, (233)
"This property is a great option! Our room was located in an elevated floor which provided great views of the city. Conveniently located in the Fulton Market area with plenty of restaurants and near by transportation. Ten-minute train ride to the loop and river walk. The property also has plenty of amenities. Including
outdoor pool
, sauna, jacuzzi, a gym and a recreational area at the 31 first floor with amazing views of the city. "
Federico
Level Chicago Fulton Market
AC Hotels by Marriott Chicago Downtown
Relax by the rectangular pool surrounded by lounge chairs and enjoy the views of the surrounding buildings.

AC Hotels by Marriott Chicago Downtown

4.0 star property
8.8 out of 10, Excellent, (1008)
"Amazing location and as close to Mag Mile as one can get without being on the main street. Rooms are generous and well designed. Love the
indoor pool
! "
Sze Hang
The price is P9,772
P11,471 total
includes taxes & fees
Aug 7 - Aug 8
AC Hotels by Marriott Chicago Downtown
Hyatt House Chicago West Loop
Relax by the pool surrounded by a spacious deck and city views.

Hyatt House Chicago West Loop

3.5 star property
8.8 out of 10, Excellent, (1020)
"Wonderful place for a family in the West Loop! The rooms are very large (especially for Chicago). Easy walk to the trains and lots of restaurants nearby. Bonus? The
pool
was great for the kiddos to get a little swimming in. The breakfast in the morning was perfect - enough yummy options for everyone. We will definitely stay again! "
Shannon
The price is P11,133
P13,069 total
includes taxes & fees
Aug 10 - Aug 11
Hyatt House Chicago West Loop
DoubleTree by Hilton Chicago - Magnificent Mile
Relax by the pool surrounded by lounge chairs and umbrellas, taking in the city skyline views.

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1913)
"Great location. Liked the property and had a great
pool
area"
Leanna
The price is P10,995
P12,907 total
includes taxes & fees
Aug 6 - Aug 7
DoubleTree by Hilton Chicago - Magnificent Mile
The Royal Sonesta Chicago River North
Relax by the pool surrounded by city views and comfortable lounge seating.

The Royal Sonesta Chicago River North

4.5 star property
9.2 out of 10, Wonderful, (1880)
"Clean and convenient hotel in a great location. The staff was very helpful and made our stay easy and enjoyable. We also had a spectacular view of the city from our room, which was a real highlight. We would absolutely stay again."
Chad
The price is P12,675
P16,687 total
includes taxes & fees
Jul 20 - Jul 21
The Royal Sonesta Chicago River North
InterContinental Chicago Magnificent Mile by IHG
Relax by the pool in a spacious area with a geometric ceiling design and large windows.

InterContinental Chicago Magnificent Mile by IHG

4.5 star property
9.0 out of 10, Wonderful, (2034)
"We especially loved the room service, but the best was the unique
indoor pool
!!"
Debra
The price is P11,252
P15,016 total
includes taxes & fees
Aug 10 - Aug 11
InterContinental Chicago Magnificent Mile by IHG
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.

Frequently asked questions

What are some accommodations with pools in Westchester?
Congress Plaza Hotel: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a steam room. InterContinental Chicago Magnificent Mile by IHG: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool, and flat-screen televisions. Hilton Chicago/Magnificent Mile Suites: Hotel, 8-minute walk from Lake Michigan. Features a 24-hour fitness center, an indoor pool, and flat-screen televisions. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 5-minute walk from Michigan Avenue. Features buffet, an indoor pool, and LCD televisions. Crowne Plaza Chicago West Loop by IHG: Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool, and complimentary wireless internet access.
What is there to see and do in Westchester?
While you're in the area, consider exploring places like 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'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.