Hotels with Swimming Pools in Hillside

  • 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 Hillside Hotels with Swimming Pools

Our top choices for Hillside hotels with a pool

Indoor pool

Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
2.5 star property
Hillside
7.0 out of 10, Good, (1,003 reviews)
  • cleanliness
    Splash into comfort at this O'Hare-area hotel with an indoor pool, perfect for all-season swims after airport arrivals.
The price is S$155
includes taxes & fees
10 May - 11 May
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
Indoor pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,384 reviews)
  • cleanliness
    Dive into urban tranquility at the Palmer House pool, where historic charm meets modern luxury.
The price is S$299
includes taxes & fees
8 May - 9 May
Palmer House a Hilton Hotel
Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,174 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 S$193
includes taxes & fees
26 Apr - 27 Apr
Aloft Chicago Mag Mile
Fitness facility

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,622 reviews)
  • cleanliness
    Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.
The price is S$343
includes taxes & fees
9 May - 10 May
Sheraton Grand Chicago Riverwalk
Indoor pool, open 5:00 AM to 11:00 PM, pool loungers

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3,751 reviews)
  • cleanliness
    Dive into the Chicago city centre hotel's refreshing indoor pool and sauna for ultimate relaxation.
The price is S$242
includes taxes & fees
26 Apr - 27 Apr
voco Chicago Downtown - Riverwalk by IHG
Indoor pool

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,085 reviews)
  • cleanliness
    Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, hot tub haven, and 24-hour fitness centre.
The price is S$253
includes taxes & fees
19 Apr - 20 Apr
Hyatt Centric Chicago Magnificent Mile
Indoor pool

Homewood Suites by Hilton Chicago-Downtown

Homewood Suites by Hilton Chicago-Downtown
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,173 reviews)
The price is S$183
includes taxes & fees
26 Apr - 27 Apr
Homewood Suites by Hilton Chicago-Downtown
Outdoor pool, 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, (2,422 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is S$219
includes taxes & fees
27 Apr - 28 Apr
DoubleTree by Hilton Chicago - Magnificent Mile
Seasonal outdoor pool

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,013 reviews)
  • cleanliness
    Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.
The price is S$305
includes taxes & fees
10 May - 11 May
The Hoxton Chicago
Indoor pool, pool loungers

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,007 reviews)
  • cleanliness
    Splash into pure relaxation at this city centre hotel's indoor pool with loungers and fitness centre access.
The price is S$384
includes taxes & fees
8 May - 9 May
Renaissance Chicago Downtown Hotel
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

Choose what matters most at hotels with a pool in Hillside

Breakfast included
Hot tub

Top Hillside Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

6/10 Okay
"Building is old- historic with fairly well maintained common areas, but also the guest areas"
Laura 3-night trip
Posted less than an hour ago
Congress Plaza Hotel

Frequently asked questions

What are some accommodation options with pools in Hillside?
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, 3-minute walk from Michigan Avenue. Features a snack bar/deli, an indoor pool and complimentary wireless Internet access. Hotel Riu Plaza Chicago: Hotel, 8-minute walk from Lake Michigan. Offers a 24-hour fitness centre, an indoor pool and flat-screen televisions. 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 Hillside?
Explore places such as Wrigley Field, Navy Pier and United Center while you're in the area. Take a walk along the waterfront at North Avenue Beach and Oak Street Beach. Travellers love Hillside for its array of dining options.
When is the best time to book a hotel with a pool in Hillside?
You may want to consider a place to stay with an outdoor swimming pool if you'll be visiting Hillside in the hottest months of July, August or June, when the average temperature is 22°C. Accommodation with an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temperature is -1°C.

Explore a world of travel with Expedia