Find Hotels with a Pool in Westchester, IL

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Check availability on Westchester Hotels with a Pool

Our top choices for Westchester hotels with a pool

Indoor pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,432 reviews)
  • cleanliness
    Dive into urban tranquility at the Palmer House pool, where historic charm meets modern luxury.
"the pool was spotless warm and very very family friendly!!"
United States
Jessica
The price is AED 639
AED 869 total
includes taxes & fees
25 May - 26 May
Palmer House a Hilton Hotel
Indoor pool, open 7:00 AM to 10:00 PM, sun loungers

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,232 reviews)
  • cleanliness
    Splash into the city at this downtown hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.
"Bonus for our trip was an indoor pool."
United States
Gail
The price is AED 551
AED 655 total
includes taxes & fees
11 May - 12 May
Aloft Chicago Mag Mile
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1,833 reviews)
  • cleanliness
    Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.
"Pool was nice and empty"
United States
Lesslee
The price is AED 621
AED 738 total
includes taxes & fees
25 May - 26 May
The Wade
Pool

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,990 reviews)
  • cleanliness
    Dive into downtown luxury with a rejuvenating pool experience close to Chicago landmarks.
"me and my family really enjoyed the hot tub and pool"
United States
Tyrea
The price is AED 464
AED 551 total
includes taxes & fees
26 May - 27 May
Hilton Garden Inn Chicago Downtown South Loop
Outdoor pool, cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,461 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
"The pool is perfect for families."
United States
Jason
The price is AED 559
AED 664 total
includes taxes & fees
25 May - 26 May
DoubleTree by Hilton Chicago - Magnificent Mile
Seasonal outdoor pool

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,011 reviews)
  • cleanliness
    Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.
"The pool was great."
United States
Jennifer
The price is AED 559
AED 772 total
includes taxes & fees
10 May - 11 May
The Hoxton Chicago
Fitness facility

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,627 reviews)
  • cleanliness
    Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.
"Pool area was amazing and family friendly."
United States
Kelly
The price is AED 790
AED 1,070 total
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk
Indoor pool

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3,048 reviews)
  • cleanliness
    World-class indoor pool in downtown offers lap swimming and family fun at this luxury hotel.
"the pool was wonderful"
United States
Joan
The price is AED 731
AED 998 total
includes taxes & fees
26 May - 27 May
InterContinental Chicago Magnificent Mile by IHG
Seasonal outdoor pool

Level Chicago - River North

Level Chicago - River North
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (989 reviews)
  • cleanliness
    Summer splashes and cityscape views await at this Chicago hotel's seasonal rooftop pool.
"Absolute best pool in the city."
United States
Sade
The price is AED 552
AED 739 total
includes taxes & fees
26 May - 27 May
Level Chicago - River North
Indoor pool

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,587 reviews)
  • cleanliness
    Stylish indoor pool retreat in downtown Chicago makes luxury laps a breeze after sightseeing.
"The view from the pool room is also beautiful."
United States
Rachelle
The price is AED 547
AED 768 total
includes taxes & fees
25 May - 26 May
The Royal Sonesta 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.
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Choose what matters most at hotels with a pool in Westchester

Breakfast included
Hot tub

Top Westchester Hotel Reviews

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

10/10 Excellent
"great location"
Julie 2-night trip
Posted 8 hours ago
Hotel Felix River North/Magnificent Mile

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Frequently asked questions

What are some accommodations with pools in Westchester?
Hotel Felix River North/Magnificent Mile: Hotel, 3-minute walk from Merchandise Mart. Features 2 restaurants, an indoor pool, and a sauna. River Hotel: Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. Hotel Riu Plaza Chicago: Hotel, 3-minute walk from Millennium Park. Features a full-service spa, an indoor pool, and a 24-hour fitness center. Congress Plaza Hotel: Hotel, 12-minute walk from Millennium Park. Offers 2 restaurants, an indoor pool, and a health club. Club Quarters Hotel, Central Loop, Chicago: Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, 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, Navy Pier, and United Center. 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.