Book the Best Hotels with POOL in Crestwood in 2026

Q: What are some hotels with pools in Crestwood?

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. Offers a snack bar/deli, an indoor pool, and complimentary wireless internet access. Hotel Riu Plaza Chicago : Hotel, 8-minute walk from Lake Michigan. Features a 24-hour fitness center, an indoor pool, and flat-screen televisions. Aloft Chicago Mag Mile : Hotel, 12-minute walk from Millennium Park. Offers 2 restaurants, an indoor pool, and a health club.

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

Swim year-round in a serene indoor pool sanctuary, where fitness and relaxation combine at this convenient train station hotel.

CA $155 total

includes taxes & fees

Apr 26 - Apr 27

Palmer House a Hilton Hotel

Downtown Chicago

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

CA $325 total

includes taxes & fees

May 8 - May 9

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.

CA $183 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.

CA $422 total

includes taxes & fees

May 9 - May 10

Homewood Suites by Hilton Chicago-Downtown

Downtown Chicago

CA $197 total

includes taxes & fees

Apr 26 - Apr 27

Renaissance Chicago Downtown Hotel

Downtown Chicago

Splash into pure relaxation at this downtown hotel's indoor pool with loungers and fitness centre access.

CA $418 total

includes taxes & fees

May 8 - May 9

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 centre.

CA $272 total

includes taxes & fees

Apr 26 - Apr 27

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

Make a splash at this downtown Chicago hotel with an indoor pool, fitness centre, and stunning city views from each room.

CA $183 total

includes taxes & fees

Apr 26 - Apr 27

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Choose what matters most at hotels with a pool in Crestwood

Breakfast included

Hot tub

Top Crestwood 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 hotels with pools in Crestwood?

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. Offers a snack bar/deli, an indoor pool, and complimentary wireless internet access. Hotel Riu Plaza Chicago: Hotel, 8-minute walk from Lake Michigan. Features a 24-hour fitness center, an indoor pool, and flat-screen televisions. Aloft Chicago Mag Mile: Hotel, 12-minute walk from Millennium Park. Offers 2 restaurants, an indoor pool, and a health club.

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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