The Best Hotels with a Pool in Hillside, IL from NT$4,028 in 2026

Q: What are some accommodations with pools in Hillside?

Congress Plaza Hotel : Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna. The Chicago Hotel Collection - Magnificent Mile : Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. Hyatt Regency O'Hare Chicago : Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool, and a sauna. Hilton Chicago O'Hare Airport : Hotel located near Donald E. Stephens Convention Center. Offers an indoor pool, an outdoor pool, and a snack bar/deli.

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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.

NT$4,028 total

includes taxes & fees

Jul 12 - Jul 13

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

NT$5,233 total

includes taxes & fees

Jun 30 - Jul 1

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

Aloft by Marriott Chicago Mag Mile

Downtown Chicago

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

NT$5,641 total

includes taxes & fees

Jul 2 - Jul 3

Sheraton Grand Chicago Riverwalk

Downtown Chicago

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

NT$8,598 total

includes taxes & fees

Jul 5 - Jul 6

Outdoor 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.

NT$7,062 total

includes taxes & fees

Jul 1 - Jul 2

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Dive into downtown luxury with a rejuvenating pool experience close to Chicago landmarks.

NT$5,520 total

includes taxes & fees

Jul 6 - Jul 7

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

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

NT$8,420 total

includes taxes & fees

Jul 1 - Jul 2

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, hot tub haven, and 24-hour fitness center.

NT$8,332 total

includes taxes & fees

Jun 30 - Jul 1

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Choose what matters most at hotels with a pool in Hillside

Breakfast included

Hot tub

Top Hillside Hotel Reviews

Hyatt Regency O'Hare Chicago

10/10 Excellent

"The room was clean and it was nice having a balcony. It was a little busy because Prom was happening but not too terribly bad. Would stay again. Beds comfortable."

Crowne Plaza Chicago West Loop by IHG

8/10 Good

"Location in West Loop is fantastic, a block away from Whole Foods and a number of great restaurants in Greek town. The staff was fantastic in addressing our needs immediately including a clogged sink and sliding door that came off the tracks. The infrastructure is a bit old and outdated. The only complaint was that we had requested a crib, which the check-in staff had reassured us would be in our room. However, it was not there when we arrived. We called to ask for one to be brought up, which took about 20 minutes. Normally, it would not be a big deal, but we arrived at 11 PM, so it was less than ideal for our toddler as it was very much past his bedtime."

Hilton Chicago O'Hare Airport

10/10 Excellent

"I really can't write a comprehensive review because we only stayed here for a short layover. Arrived at midnight and left at 5:30. I can, however, say that the hotel was clean, check-in was efficient and location was great as we were able to walk from our plane to the hotel in under 10 minutes. Just what we were looking for. Of course, I wish the price was less especially since we were only there for 5 hours, but it met our needs and we were able to rest for a little while before making our connection. I wish all airports had this convenient hotel choice on site."

Frequently asked questions

What are some accommodations with pools in Hillside?

Congress Plaza Hotel: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna. The Chicago Hotel Collection - Magnificent Mile: Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. Hyatt Regency O'Hare Chicago: Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool, and a sauna. Hilton Chicago O'Hare Airport: Hotel located near Donald E. Stephens Convention Center. Offers an indoor pool, an outdoor pool, and a snack bar/deli.

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.

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