The Best Hotels with a Pool in Countryside, IL from NT$4,298 in 2026

Q: What are some accommodations with pools in Countryside?

Congress Plaza Hotel : Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. Hilton Chicago/Magnificent Mile Suites : Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool, and flat-screen televisions. Embassy Suites by Hilton Chicago Downtown River North : Hotel, 3-minute walk from Michigan Avenue. Features a snack bar/deli, an indoor pool, and complimentary wireless internet access. Hotel Riu Plaza Chicago : Hotel, 8-minute walk from Lake Michigan. Offers a 24-hour fitness center, an indoor pool, and flat-screen televisions. Hilton Chicago O'Hare Airport : Hotel, 12-minute walk from Millennium Park. Features 2 restaurants, an indoor pool, and a health club.

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Our top choices for Countryside hotels with a pool

Palmer House a Hilton Hotel

Downtown Chicago

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

NT$6,757 total

includes taxes & fees

May 9 - May 10

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

Aloft 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$4,779 total

includes taxes & fees

Apr 26 - Apr 27

Sheraton Grand Chicago Riverwalk

Downtown Chicago

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

NT$9,703 total

includes taxes & fees

May 9 - May 10

The Wade

Downtown Chicago

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

NT$7,372 total

includes taxes & fees

Apr 26 - Apr 27

The Hoxton Chicago

Downtown Chicago

Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.

NT$7,308 total

includes taxes & fees

May 10 - May 11

Indoor pool, outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

Eaglewood Resort and Spa

Itasca

Aquatic elegance meets relaxation at this resort's indoor pool sanctuary, featuring plush sun loungers and protective umbrellas.

NT$4,298 total

includes taxes & fees

May 17 - May 18

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

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

NT$4,908 total

includes taxes & fees

Apr 26 - Apr 27

Indoor pool, seasonal outdoor pool, free cabanas, sun loungers

Radisson Blu Aqua Hotel Chicago

Downtown Chicago

Luxurious indoor and seasonal outdoor pools form a relaxing oasis near Millennium Park and Michigan Avenue.

NT$9,041 total

includes taxes & fees

May 9 - May 10

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Choose what matters most at hotels with a pool in Countryside

Breakfast included

Hot tub

Top Countryside Hotel Reviews

The Wade

10/10 Excellent

"Friendly staff, clean room and clean common places. Gym and pool area were nice too"

Eurostars Magnificent Mile

10/10 Excellent

"The only negative note I had was I wanted to be able to go to my balcony to check out the city from my room but besides that. I had a WONDERFUL stay. The rooms were nicely organized and cleaned and the showers felt amazing. If I ever go to Chicago, i will definitely book with them again! "

DoubleTree by Hilton Chicago - Magnificent Mile

4/10 Poor

"Unfortunately it wasn’t a great stay. Our room was not serviced for two of the four days, despite asking for it. In addition, the outdoor pool was closed for the duration of the stay despite being advertised on booking and was one of the reasons the hotel was booked. Breakfast was good but has an awkward system where a credit is allocated and if it’s exceeded it’s charged to your room, could be better. "

Frequently asked questions

What are some accommodations with pools in Countryside?

Congress Plaza Hotel: Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. Hilton Chicago/Magnificent Mile Suites: Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool, and flat-screen televisions. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 3-minute walk from Michigan Avenue. Features a snack bar/deli, an indoor pool, and complimentary wireless internet access. Hotel Riu Plaza Chicago: Hotel, 8-minute walk from Lake Michigan. Offers a 24-hour fitness center, an indoor pool, and flat-screen televisions. Hilton Chicago O'Hare Airport: Hotel, 12-minute walk from Millennium Park. Features 2 restaurants, an indoor pool, and a health club.

What is there to see and do in Countryside?

Explore places like Navy Pier, Wrigley Field, and United Center while you're in the area. Enjoy a stroll along the shore at Centennial Beach and Oak Street Beach. Travelers love Countryside for its array of dining options.

When is the best time to book a hotel with a pool in Countryside?

You may want to consider a place to stay that has an outdoor pool if you're planning to visit Countryside in the hottest months of July, August, or June when the average temp is 71°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temperature is 31°F.

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