TOP Hotels with Swimming Pool in Hillside, IL for 2026

Q: What are some accommodation options with pools in Hillside?

Congress Plaza Hotel : Hotel, 3-minute walk from Merchandise Mart. Features 2 restaurants, an indoor pool and a sauna. River Hotel : Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool and a health club. Hotel Riu Plaza Chicago : Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. 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. Hotel Felix River North/Magnificent Mile : Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool and flat-screen televisions.

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Our top choices for Hillside hotels with a pool

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

Hillside

Splash into comfort at this O'Hare-area hotel with an indoor pool, perfect for all-season swims after airport arrivals.

₹12,711 total

includes taxes & fees

27 May - 28 May

Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Splash into the city at this city centre hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.

₹16,953 total

includes taxes & fees

26 May - 27 May

The Wade

Downtown Chicago

Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.

₹18,414 total

includes taxes & fees

25 May - 26 May

Palmer House a Hilton Hotel

Downtown Chicago

Dive into urban tranquility at the Palmer House pool, where historic charm meets modern luxury.

₹26,509 total

includes taxes & fees

26 May - 27 May

Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.

₹19,230 total

includes taxes & fees

25 May - 26 May

Homewood Suites by Hilton Chicago-Downtown

Downtown Chicago

₹18,169 total

includes taxes & fees

25 May - 26 May

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

World-class indoor pool in city centre offers lap swimming and family fun at this luxury hotel.

₹27,614 total

includes taxes & fees

27 May - 28 May

Holiday Inn Chicago Dwtn - The Mart by IHG

Downtown Chicago

Float in style at this Chicago riverside retreat with a sleek indoor pool, two on-site restaurants, and skyline views.

₹20,366 total

includes taxes & fees

25 May - 26 May

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Choose what matters most at hotels with a pool in Hillside

Breakfast included

Hot tub

Top Hillside Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"One of the secrets of Chicago breakfasts. 🍳 Such a fun place and well located."

Frequently asked questions

What are some accommodation options with pools in Hillside?

Congress Plaza Hotel: Hotel, 3-minute walk from Merchandise Mart. Features 2 restaurants, an indoor pool and a sauna. River Hotel: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool and a health club. Hotel Riu Plaza Chicago: Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. 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. Hotel Felix River North/Magnificent Mile: Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool and flat-screen televisions.

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.

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