Book the Best Hotels with POOL in Crestwood in 2026

Q: What are some hotels with pools in Crestwood?

River Hotel : Hotel, 2-minute walk from Grant Park. Features 2 restaurants, an indoor pool, and a health club. Congress Plaza Hotel : Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna. The Chicago Hotel Collection Ambassador Gold Coast : Hotel, 8-minute walk from Lake Michigan. Offers complimentary wireless internet access, an indoor pool, and a 24-hour fitness center.

A serene lake with reflections of trees and a cloudy sky.

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Our top choices for Crestwood hotels with a pool

A spacious lobby with a central seating area, a reception desk, and a modern chandelier.

1. DoubleTree by Hilton Chicago - Alsip

Alsip

Swimming laps of luxury in Chicago's only indoor hotel pool with cushy loungers.

CA $180 total

includes taxes & fees

Nov 22 - Nov 23

An indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

2. Hilton Chicago/Oak Lawn

Oak Lawn

Dive into year-round aquatic bliss with an indoor pool and 24-hour fitness centre complemented by friendly, professional service.

CA $197 total

includes taxes & fees

Nov 5 - Nov 6

3. Holiday Inn Express & Suites Chicago - Oak Forest by IHG

Oak Forest

Splash into all-weather aquatic fun at this Chicago hotel's sparkling indoor pool oasis.

CA $197 total

includes taxes & fees

Nov 15 - Nov 16

4. Hampton Inn Chicago / Tinley Park

Tinley Park

Dive into cool-vibes heaven at this indoor pool oasis with hydromassage showers.

CA $173 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with a no diving sign, lounge chairs, and a lifeguard chair.

5. Hampton Inn Chicago Orland Park

Orland Park

Refreshing indoor pool retreat near Chicago awaits with complimentary breakfast and premium bedding.

CA $166 total

includes taxes & fees

Nov 22 - Nov 23

A swimming pool with lounge chairs and a view of the outside.

6. Wingate by Wyndham Tinley Park

Tinley Park

Luxurious indoor pool and hot tub sanctuary creates a rejuvenating aquatic retreat in Tinley Park.

CA $188 total

includes taxes & fees

Nov 22 - Nov 23

An indoor swimming pool with clear blue water, surrounded by walls with large windows offering views of trees and buildings.

7. Hampton Inn & Suites Bridgeview Chicago

Summit

Soak in tranquility at this modern Chicago hotel with an inviting indoor pool, loungers, and 24-hour fitness centre nearby.

CA $178 total

includes taxes & fees

Nov 23 - Nov 24

A swimming pool with a tiled deck, lounge chairs, and a view of the outside.

8. Holiday Inn Chicago Tinley Park by IHG

Tinley Park

Make a splash at this hotel with an indoor pool for all-weather swimming and stellar service.

CA $208 total

includes taxes & fees

Nov 23 - Nov 24

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Choose what matters most at hotels with a pool in Crestwood

Breakfast included

Hot tub

Top Crestwood Hotel Reviews

Congress Plaza Hotel

10/10 Excellent

"."

Sports Illustrated Resorts Chicago

8/10 Good

"Solid hotel in a great location. We were there as they were transferring to a full launch of the SI branded hotel. Good gym, rooms are well appointed. During our visit they had an all inclusive rooftop bar from 3-7pm every day which was a great touch but nobody actually told us about it, we kind of found it ourselves. Good option for a hotel in downtown Chicago though!"

Frequently asked questions

What are some hotels with pools in Crestwood?

River Hotel: Hotel, 2-minute walk from Grant Park. Features 2 restaurants, an indoor pool, and a health club. Congress Plaza Hotel: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna. The Chicago Hotel Collection Ambassador Gold Coast: Hotel, 8-minute walk from Lake Michigan. Offers complimentary wireless internet access, an indoor pool, and a 24-hour fitness center.

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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