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

Hotels with Swimming Pool in Hillside, Chicago

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on Hillside Hotels with Swimming Pool

This weekend
Next weekend

Our top choices for Hillside hotels with a pool

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,483 reviews)
The price is P11,635
P13,833 total
includes taxes & fees
Jul 5 - Jul 6
Hilton Chicago/Magnificent Mile Suites

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,688 reviews)
  • cleanliness
    Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.
The price is P15,329
P20,421 total
includes taxes & fees
Jul 5 - Jul 6
Sheraton Grand Chicago Riverwalk

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, (5,988 reviews)
  • cleanliness
    Slip into a vacation state of mind at Chicago's urban retreat with a sparkling indoor pool.
The price is P10,404
P12,369 total
includes taxes & fees
Jul 5 - Jul 6
Embassy Suites by Hilton Chicago Downtown River North

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, (1,002 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 P7,511
P8,410 total
includes taxes & fees
Jul 19 - Jul 20
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

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, (2,877 reviews)
  • cleanliness
    Chicago hotel offers refreshing stays with indoor pool, fitness center, and walkable Michigan Avenue access.
The price is P11,183
P15,104 total
includes taxes & fees
Jul 6 - Jul 7
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,299 reviews)
  • cleanliness
    Splash into the city at this downtown hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.
The price is P8,619
P10,247 total
includes taxes & fees
Jul 5 - Jul 6
Aloft by Marriott Chicago Mag Mile

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3,122 reviews)
  • cleanliness
    World-class indoor pool in downtown offers lap swimming and family fun at this luxury hotel.
The price is P15,329
P20,380 total
includes taxes & fees
Jul 6 - Jul 7
InterContinental Chicago Magnificent Mile by IHG

Homewood Suites by Hilton Chicago-Downtown

Homewood Suites by Hilton Chicago-Downtown
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,226 reviews)
The price is P12,251
P14,566 total
includes taxes & fees
Jul 5 - Jul 6
Homewood Suites by Hilton Chicago-Downtown

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,510 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is P11,020
P13,102 total
includes taxes & fees
Jul 5 - Jul 6
DoubleTree by Hilton Chicago - Magnificent Mile

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,500 reviews)
  • cleanliness
    Dive into urban tranquility at the Palmer House pool, where historic charm meets modern luxury.
The price is P15,021
P19,689 total
includes taxes & fees
Jul 6 - Jul 7
Palmer House a Hilton 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.

Choose what matters most at hotels with a pool in Hillside

Top Hillside Hotel Reviews

Frequently asked questions

What are some accommodations 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 center. 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 like 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. Travelers 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 that offers an outdoor pool if you will be visiting Hillside in the hottest months of July, August, or June when the average temperature is 71°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 30°F.

Explore a world of travel with Expedia