Book the Best Hotels with POOL in Countryside in 2026

Q: What are some accommodations with pools in Countryside?

Congress Plaza Hotel : Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool, and a sauna. Hotel Riu Plaza Chicago : Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool, and complimentary wireless internet access. The Chicago Hotel Collection - Magnificent Mile : Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. River Hotel : Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool, and flat-screen televisions. Hotel Felix River North/Magnificent Mile : Hotel, 5-minute walk from Michigan Avenue. Provides a rooftop terrace, a seasonal outdoor pool, and LED televisions.

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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.

CA $353 total

includes taxes & fees

Jul 2 - Jul 3

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

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

CA $424 total

includes taxes & fees

Jul 1 - Jul 2

Sheraton Grand Chicago Riverwalk

Downtown Chicago

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

CA $376 total

includes taxes & fees

Jul 2 - Jul 3

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

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

CA $250 total

includes taxes & fees

Jul 1 - Jul 2

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.

CA $388 total

includes taxes & fees

Jul 1 - Jul 2

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.

CA $199 total

includes taxes & fees

Jun 7 - Jun 8

The Royal Sonesta Chicago River North

Downtown Chicago

Stylish indoor pool retreat in downtown Chicago makes luxury laps a breeze after sightseeing.

CA $338 total

includes taxes & fees

Jul 1 - Jul 2

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.

CA $274 total

includes taxes & fees

Jun 29 - Jun 30

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Choose what matters most at hotels with a pool in Countryside

Breakfast included

Hot tub

Top Countryside Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"fun"

Eurostars Magnificent Mile

8/10 Good

"Overall, our stay at Eurostars Hotel was pleasant, and the staff was courteous and accommodating. However, we experienced an issue with the room doors. Our initial room had a door that did not appear to close properly, leaving a noticeable gap that allowed conversations and other sounds from inside the room to be heard from the hallway. This became apparent when someone outside the room was able to hear activity inside and came to our door. The staff promptly moved us to another room, but we encountered the same issue, with an even larger gap around the door. We were informed that all rooms on that side of the hotel have similar door gaps and that no other rooms were available for relocation. While we appreciated the staff’s efforts to address our concerns, the lack of privacy caused by the door condition negatively impacted our stay."

Frequently asked questions

What are some accommodations with pools in Countryside?

Congress Plaza Hotel: Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool, and a sauna. Hotel Riu Plaza Chicago: Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool, and complimentary wireless internet access. The Chicago Hotel Collection - Magnificent Mile: Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. River Hotel: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool, and flat-screen televisions. Hotel Felix River North/Magnificent Mile: Hotel, 5-minute walk from Michigan Avenue. Provides a rooftop terrace, a seasonal outdoor pool, and LED televisions.

What is there to see and do in Countryside?

Explore places like Soldier Field, Michigan Avenue, and Navy Pier 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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