The Best Hotels with a Pool in Crestwood, IL in 2026

Q: What are some hotels with pools in Crestwood?

The Chicago Hotel Collection Ambassador Gold Coast : Hotel, 3-minute walk from Merchandise Mart. Features 2 restaurants, an indoor pool, and a sauna. Omni Chicago Hotel : Hotel steps from 875 North Michigan Avenue. Provides flat-screen televisions and an indoor pool. Congress Plaza Hotel : Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Hotel Riu Plaza Chicago : Hotel, 10-minute walk from University of Illinois Chicago. Offers a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access.

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Our top choices for Crestwood hotels with a pool

DoubleTree by Hilton Chicago - Alsip

Alsip

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

NT$4,762 total

includes taxes & fees

Aug 12 - Aug 13

Hilton Chicago/Oak Lawn

Oak Lawn

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

NT$4,847 total

includes taxes & fees

Aug 17 - Aug 18

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.

NT$3,883 total

includes taxes & fees

Aug 9 - Aug 10

Wingate by Wyndham Tinley Park

Tinley Park

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

NT$4,734 total

includes taxes & fees

Aug 10 - Aug 11

Hampton Inn Chicago Orland Park

Orland Park

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

NT$4,423 total

includes taxes & fees

Aug 9 - Aug 10

Country Inn & Suites by Radisson, Tinley Park, IL

Tinley Park

Splash into relaxation at this inviting hotel with an indoor pool that welcomes swimmers year-round regardless of weather.

NT$4,076 total

includes taxes & fees

Aug 2 - Aug 3

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.

NT$4,739 total

includes taxes & fees

Aug 4 - Aug 5

Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Bridgeview Chicago

Summit

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

NT$5,056 total

includes taxes & fees

Aug 18 - Aug 19

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Choose what matters most at hotels with a pool in Crestwood

Breakfast included

Hot tub

Top Crestwood Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Great location. Large rooms. Wish the pool stayed open later."

Congress Plaza Hotel

10/10 Excellent

"Wonderful location - we were right across from Buckingham Fountain. From the 11th floor, we had a great view of the lake. Old style elegance. The a/c - heating system is of a different era. I would not book a lake side room during the height of the summer - I don't think the system could keep up."

Eurostars Magnificent Mile

10/10 Excellent

"Ideal stay as this place is in the middle of everything so it was a great blind pick. So being in the center of everything means you will hear ambulances like crazy however, you can walk to many places easily. The hotel itself is nice and well kept up in common areas. Not all rooms are as kept up/maintained- other than changing sheets and replacing towels, as they should be. Kept up meaning, touching up extreme nicks and natural wear n tear that occurs when hundreds of people are in and out constantly. Keeping things maintained and fresh seems ideal as this is what is advertised online so it is expected. The issue with my room was quickly rectified by a male staffer at the front desk. He was quick and extremely efficient in handling my situation. I appreciated the fantastic customer service. I did not use room service but there’s a fantastic restaurant as you enter the hotel. Very nice."

The Wade

8/10 Good

"Why book here? LOCATION and competitive price. Why not? If you care about hospitality. This isn't going to be the place. Some of the front desk staff were impatient and border line dismissive. No decaf, despite a sign saying it was available. Just plan to go to Starbucks about a block away for coffee of any quality. Check in evening staff, told us breakfast would be served (Marriott member) and then we weren't given the magic card. Morning staff said we didn't qualify and we got the signal NOT to bother them with unreasonable questions. Our room was next to elevator and I was glad I had my ear plugs. No coffee in rooms. Weird kinda sensual picture of red lips predominant art in room... not family friendly or sensitive to women's modern issues. Views of lake were great! Easy walking location to see Lake Shore Drive and Many other great attractions. LOVED the beach and lake. It is amazingly clear water. Just have realistic expectations that this is a place to sleep and the staff may not care or are burned out. Great service oriented humans are expensive. You're not paying for that here."

The Royal Sonesta Chicago Downtown

8/10 Good

"One main concern with the room is the rainfall shower head. It’s not conducive to Black hair as we don't fully immerse out head in water during showers. Even pushing the head towards the wall offered minimal help. Breakfast at Hoyt is expensive and there isnt much variety on the menu. The location of the hotel is perfectly near the Riverwalk. Microwaves are available upon request. Early checkin is an option at a cost unless u are a rewards member. There is no pool plus a $30 a day non refundable resort fee AND a $100 a day deposit. My opinion, not much bang for your buck. The hotel was emailed 2 weeks prior to my arrival in order to plan something special however the email was never answered."

Frequently asked questions

What are some hotels with pools in Crestwood?

The Chicago Hotel Collection Ambassador Gold Coast: Hotel, 3-minute walk from Merchandise Mart. Features 2 restaurants, an indoor pool, and a sauna. Omni Chicago Hotel: Hotel steps from 875 North Michigan Avenue. Provides flat-screen televisions and an indoor pool. Congress Plaza Hotel: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Hotel Riu Plaza Chicago: Hotel, 10-minute walk from University of Illinois Chicago. Offers a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access.

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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