Find Hotels with a Pool in Oak Park, IL

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Oak Park Hotels with a Pool

Our top choices for Oak Park hotels with a pool

Pool
Hilton Garden Inn Chicago Downtown South Loop

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, (1748)
"Clean and staff was courteous. "
United States
HANNAH
The price is AED 262
AED 307 total
includes taxes & fees
5 Jan - 6 January 2026
Hilton Garden Inn Chicago Downtown South Loop
Indoor pool, open 5:00 AM to 11:00 PM, sun loungers
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3454)
"Great value and location"
United States
Kelly
The price is AED 411
AED 483 total
includes taxes & fees
29 Dec - 30 Dec
voco Chicago Downtown - Riverwalk by IHG
Indoor pool, open 7:00 AM to 10:00 PM, sun loungers
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2948)
"Great location and great staff!!"
United States
lynne
The price is AED 283
AED 332 total
includes taxes & fees
15 Dec - 16 Dec
Aloft Chicago Mag Mile
Outdoor pool, cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2180)
"Nice Hotel"
United States
Alan
The price is AED 328
AED 385 total
includes taxes & fees
21 Dec - 22 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (5367)
"excellent hotel "
United States
Myounghee
The price is AED 367
AED 431 total
includes taxes & fees
4 Jan - 5 January 2026
Embassy Suites by Hilton Chicago Downtown River North
Indoor pool
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1045)
"Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food."
United States
Hannah
The price is AED 359
AED 529 total
includes taxes & fees
3 Jan - 4 January 2026
Hyatt Centric Chicago Magnificent Mile
Pool
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2128)
"Very nice place"
United States
Salman
The price is AED 291
AED 341 total
includes taxes & fees
5 Jan - 6 January 2026
Homewood Suites by Hilton Chicago Downtown South Loop
Indoor pool
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2133)
"Loved and enjoyed our stay"
United States
Luis
The price is AED 407
AED 569 total
includes taxes & fees
21 Dec - 22 Dec
Palmer House a Hilton Hotel
Indoor pool
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2036)
"room was good,location was perfect!"
United States
Kyan
The price is AED 360
AED 423 total
includes taxes & fees
24 Dec - 25 Dec
Holiday Inn Chicago Dwtn - The Mart by IHG
Indoor pool
The Wade

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1509)
"Everything was really wonderful.. would stay again for sure!! "
United States
Alexa
The price is AED 371
AED 435 total
includes taxes & fees
15 Dec - 16 Dec
The Wade
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.
View all properties

Top Oak Park Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Lovely hotel."
Cedrick 2-night trip
Posted 11 hours ago
Crowne Plaza Chicago West Loop by IHG

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Oak Park?
Palmer House a Hilton Hotel: Hotel steps from State Street. Features a full-service spa, an indoor pool, and a 24-hour fitness center. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool, and flat-screen televisions. Hilton Chicago/Magnificent Mile Suites: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel: Hotel, 4-minute walk from State Street. Features 2 restaurants, an indoor pool, and a health club.
What is there to see and do in Oak Park?
Explore places like Wrigley Field, Michigan Avenue, and United Center while you're in the area. Take in the natural beauty with a stop at Oak Park Conservatory. Oak Park appeals to visitors with its array of dining options and major shopping area.
When is the best time to book a hotel with a pool in Oak Park?
You may want to think about a place to stay that has an outdoor pool if you plan to visit Oak Park in the hottest months of July, August, or June when the average temp is 71°F. Lodging offering 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 temperature is 31°F.
What's the best way to travel around Oak Park?
Knowing the transportation options in Oak Park can help you enjoy the area beyond your hotel pool. You can take advantage of metro transit at Ridgeland Station (Green Line), Oak Park Station (Green Line), and Oak Park Station (Blue Line). To see more of the larger area, ride aboard one of the trains from Oak Park Station.