TOP Hotels with Swimming Pool in Hillside, IL for 2026

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

Congress Plaza Hotel : Hotel, 2-minute walk from Michigan Avenue. Provides flat-screen televisions and an indoor pool. Omni Chicago Hotel : Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool and a sauna. Hilton Chicago/Magnificent Mile Suites : Hotel, 3-minute walk from Millennium Park. Provides a full-service spa, an indoor pool and a 24-hour fitness centre. Hyatt Regency O'Hare Chicago : Hotel, 3-minute walk from Merchandise Mart. Provides 2 restaurants, an indoor pool and a sauna.

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

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Our top choices for Hillside hotels with a pool

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.

₹22,798 total

includes taxes & fees

19 Jul - 20 Jul

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Chicago hotel offers refreshing stays with indoor pool, fitness centre, and walkable Michigan Avenue access.

₹31,590 total

includes taxes & fees

19 Jul - 20 Jul

Indoor pool, open 6:00 AM to 10:00 PM, pool loungers

Sheraton Grand Chicago Riverwalk

Downtown Chicago

Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.

₹36,183 total

includes taxes & fees

6 Aug - 7 Aug

Palmer House a Hilton Hotel

Downtown Chicago

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

₹35,049 total

includes taxes & fees

6 Aug - 7 Aug

Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Slip into a holiday state of mind at Chicago's urban retreat with a sparkling indoor pool.

₹23,194 total

includes taxes & fees

19 Jul - 20 Jul

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.

₹34,533 total

includes taxes & fees

19 Jul - 20 Jul

Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Splash into city centre luxury at this Hampton Inn with stylish indoor pool and river proximity.

₹24,386 total

includes taxes & fees

8 Jul - 9 Jul

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

₹24,343 total

includes taxes & fees

19 Jul - 20 Jul

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Choose what matters most at hotels with a pool in Hillside

Breakfast included

Hot tub

Top Hillside Hotel Reviews

Omni Chicago Hotel

10/10 Excellent

"Convenient location and friendly staff."

Warwick Allerton - Chicago

8/10 Good

"This hotel is perfectly acceptable, and convenient for its proximity to Northwestern Hospital. The bed was not made for a great nights sleep. The TV was painfully small and the options were paltry. I've stayed in much lower cost hotels that had better options. Every Chicago hotel should be up to date in offering connectivity to streaming services. Also, the lack of conditioner and lotion in the bathroom was annoying. This was a last minute stay for medical appointments, so when I packed quickly, I expected certain amenities that were not there."

Holiday Inn & Suites Chicago - Downtown by IHG

8/10 Good

"It was great to find a clean, comfortable room close to union station. I am in a wheelchair so the steep driveway to get into the property was a bit difficult to navigate but other than that access was easy. The room had ADA accommodations that I needed and although the room was small for a wheelchair, there were innovative solutions, like wheels on the small table, so that everything worked."

Frequently asked questions

What are some accommodation options with pools in Hillside?

Congress Plaza Hotel: Hotel, 2-minute walk from Michigan Avenue. Provides flat-screen televisions and an indoor pool. Omni Chicago Hotel: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool and a sauna. Hilton Chicago/Magnificent Mile Suites: Hotel, 3-minute walk from Millennium Park. Provides a full-service spa, an indoor pool and a 24-hour fitness centre. Hyatt Regency O'Hare Chicago: Hotel, 3-minute walk from Merchandise Mart. Provides 2 restaurants, an indoor pool and a sauna.

What is there to see and do in Hillside?

Explore places such as United Center, Wrigley Field and Michigan Avenue 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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