A lush green valley with a winding road, steep mountains, and a misty atmosphere.

Hillside Hotels with Swimming Pool

  • 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

Next weekend
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul

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
7.2 out of 10, Good, (1,004 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 RM480
RM538 total
includes taxes & fees
12 Jul - 13 Jul
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,307 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 RM725
RM862 total
includes taxes & fees
7 Jul - 8 Jul
Aloft by Marriott Chicago Mag Mile
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,893 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 RM688
RM818 total
includes taxes & fees
7 Jul - 8 Jul
The Wade
Indoor pool

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, (2,891 reviews)
  • cleanliness
    Chicago hotel offers refreshing stays with indoor pool, fitness centre, and walkable Michigan Avenue access.
The price is RM851
RM1,131 total
includes taxes & fees
7 Jul - 8 Jul
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
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, (2,513 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is RM810
RM963 total
includes taxes & fees
7 Jul - 8 Jul
DoubleTree by Hilton Chicago - Magnificent Mile
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, (3,131 reviews)
  • cleanliness
    World-class indoor pool in city centre offers lap swimming and family fun at this luxury hotel.
The price is RM1,087
RM1,435 total
includes taxes & fees
19 Jul - 20 Jul
InterContinental Chicago Magnificent Mile by IHG
Indoor pool

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,507 reviews)
The price is RM769
RM915 total
includes taxes & fees
7 Jul - 8 Jul
Hilton Chicago/Magnificent Mile Suites
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, (1,231 reviews)
The price is RM760
RM904 total
includes taxes & fees
9 Jul - 10 Jul
Homewood Suites by Hilton Chicago-Downtown
Indoor pool

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,945 reviews)
The price is RM794
RM944 total
includes taxes & fees
7 Jul - 8 Jul
Courtyard by Marriott Chicago Magnificent Mile
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, (2,689 reviews)
  • cleanliness
    Stylish indoor pool retreat in city centre Chicago makes luxury laps a breeze after sightseeing.
The price is RM757
RM1,031 total
includes taxes & fees
8 Jul - 9 Jul
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.
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

10/10 Excellent
"This will always be my go to place to stay in downtown Chicago. Fantastic location, clean and great staff."
Allison 1-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 steps from State Street. Features a full-service spa, an indoor pool and a 24-hour fitness centre. The Chicago Hotel Collection - Magnificent Mile: Hotel steps from Michigan Avenue. Provides 2 restaurants, an indoor pool and a sauna.
What is there to see and do in Hillside?
Explore places such as Wrigley Field, Michigan Avenue and Soldier Field 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