The Best Hotels with a Pool in Crestwood, IL from NT$2,797 in 2026

Q: What are some hotels with pools in Crestwood?

Hilton Chicago : Hotel, 4-minute walk from State Street. Features 2 restaurants, an indoor pool, and a health club. Hilton Chicago/Magnificent Mile Suites : Hotel steps from State Street. Features a full-service spa, an indoor pool, and a 24-hour fitness center. Club Quarters Hotel Wacker at Michigan, Chicago : Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool, and flat-screen televisions. Palmer House a Hilton Hotel : Hotel, 14-minute walk from Chicago Riverwalk. Offers 2 restaurants, an indoor pool, and a sauna. Embassy Suites by Hilton Chicago Downtown River North : Hotel, 5-minute walk from Michigan Avenue. Offers a rooftop terrace, a seasonal outdoor pool, and LED televisions.

Reflection on Lake at Dusk at Turtlehead Lake Nature Preserve in Orland Park, IL (Suburban Chicago)

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Our top choices for Crestwood hotels with a pool

Holiday Inn Express Crestwood by IHG

Crestwood

Heather

NT$2,900 total

includes taxes & fees

Jan 19 - Jan 20

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

Aloft Chicago Mag Mile

Downtown Chicago

Alec

NT$2,804 total

includes taxes & fees

Jan 25 - Jan 26

Outdoor pool, cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Jeffrey

NT$3,161 total

includes taxes & fees

Feb 1 - Feb 2

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

ANN

NT$2,797 total

includes taxes & fees

Feb 8 - Feb 9

Indoor pool, open 5:00 AM to 11:00 PM, sun loungers

voco Chicago Downtown - Riverwalk by IHG

Downtown Chicago

Shaurya

NT$4,300 total

includes taxes & fees

Feb 15 - Feb 16

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Lorenzo Martrel

NT$2,979 total

includes taxes & fees

Jan 25 - Jan 26

Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

Ashley

NT$3,752 total

includes taxes & fees

Feb 5 - Feb 6

Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Manish Mani

NT$3,013 total

includes taxes & fees

Feb 16 - Feb 17

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Top Crestwood Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Great stay. "

Frequently asked questions

What are some hotels with pools in Crestwood?

Hilton Chicago: Hotel, 4-minute walk from State Street. Features 2 restaurants, an indoor pool, and a health club. Hilton Chicago/Magnificent Mile Suites: Hotel steps from State Street. Features a full-service spa, an indoor pool, and a 24-hour fitness center. Club Quarters Hotel Wacker at Michigan, Chicago: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool, and flat-screen televisions. Palmer House a Hilton Hotel: Hotel, 14-minute walk from Chicago Riverwalk. Offers 2 restaurants, an indoor pool, and a sauna. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 5-minute walk from Michigan Avenue. Offers a rooftop terrace, a seasonal outdoor pool, and LED televisions.

What is there to see and do in Crestwood?

Explore places like Soldier Field while you're in the area. Make a point to visit attractions like Hollywood Park. The restaurants and shopping are just some of the things to enjoy while you're in the area.

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

You may want to consider an accommodation that has an outdoor pool if you will be visiting Crestwood in the warmest months of July, August, or June when the average temp is 71°F. Lodging with an indoor pool may be what you want if you come to town during the coldest months of January, February, or December when the average temp is 31°F.

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