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

Find Hotels with a Pool in Crestwood, IL

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Check availability on Crestwood Hotels with a Pool

Tonight
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Crestwood hotels with a pool

A rooftop terrace with a glass floor, offering a view of the city skyline.
A bar area with a marble countertop, bar stools, and a variety of bottles.
A spacious lobby with a marble floor, a reception desk, and a glass partition.
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

1. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
Downtown Chicago
$209 nightly
$249 total
Nov 11 - Nov 12
Total with taxes and fees
Hotel Riu Plaza Chicago
An indoor swimming pool with clear lane markers, a tiled floor, and ceiling beams.
An outdoor dining area with brick walls, string lights, and tables set for guests.
A spacious lobby with a central seating area, a reception desk, and a modern chandelier.
A hotel lobby with seating areas, a patterned carpet, and a large mirror.

2. DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip
Alsip
  • Swimming laps of luxury in Chicago's only indoor hotel pool with cushy loungers.
$121 nightly
$136 total
Nov 1 - Nov 2
Total with taxes and fees
DoubleTree by Hilton Chicago - Alsip
An indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.
A modern bar area with a long counter, multiple bar stools, and a variety of bottles on shelves.
A spacious indoor area with a long table, multiple chairs, a sofa, and several gaming machines.
A spacious lobby with a reception desk, seating area, and a modern chandelier.

3. Hilton Chicago/Oak Lawn

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.
$130 nightly
$150 total
Nov 1 - Nov 2
Total with taxes and fees
Hilton Chicago/Oak Lawn
Pool
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

4. Hilton Chicago

Hilton Chicago
Downtown Chicago
  • Soak in relaxation at this historic Chicago hotel's indoor pool with spa amenities nearby.
$194 nightly
$230 total
Nov 13 - Nov 14
Total with taxes and fees
Hilton Chicago
A swimming pool with lounge chairs and sun loungers, a tiled floor, and a large window with curtains.
A cityscape at dusk with high-rise buildings, including a Hilton hotel.
A hotel room with a bed, a desk, a television, a sofa, and a large window with a city view.
A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.

5. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
$161 nightly
$191 total
Nov 1 - Nov 2
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites
An indoor swimming pool with lounge chairs and a sofa, large windows with a view of the city, and a high ceiling with skylights.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.
A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.
A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.

6. The Wade

The Wade
Downtown Chicago
  • Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.
$164 nightly
$195 total
Nov 10 - Nov 11
Total with taxes and fees
The Wade
An indoor swimming pool area with a view of the pool, a table with chairs, and a potted plant.
A modern dining area with a long table, blue chairs, and a coffee station.
A Holiday Inn Express building with a covered entrance and a parking lot.
A modern bathroom with a shower, toilet, sink, and mirror.

7. Holiday Inn Express Crestwood by IHG

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.
$110 nightly
$123 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express Crestwood by IHG
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.
A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.
A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.
A person sitting by a window with a cityscape view.

8. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
  • World-class indoor pool in downtown offers lap swimming and family fun at this luxury hotel.
$241 nightly
$287 total
Oct 31 - Nov 1
Total with taxes and fees
InterContinental Chicago Magnificent Mile by IHG
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.
A hotel reception area with a modern design, featuring a wooden panel wall and a marble reception desk.
Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.
A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.

9. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
Downtown Chicago
  • Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
$127 nightly
$151 total
Nov 1 - Nov 2
Total with taxes and fees
DoubleTree by Hilton Chicago - Magnificent Mile
A swimming pool with a glass wall, a seating area with sofas, and an exit sign.
A spacious lobby with a central staircase, multiple floors, a reception desk, and seating areas.
A multi-story hotel with a prominent 'Embassy Suites' sign, a Starbucks Coffee shop, and a well-lit street at night.
A multi-level indoor area with a central water feature, surrounded by seating areas and greenery.

10. Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
  • Slip into a vacation state of mind at Chicago's urban retreat with a sparkling indoor pool.
$152 nightly
$181 total
Nov 1 - Nov 2
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North
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Choose what matters most at hotels with a pool in Crestwood

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Crestwood Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Room is spacious, very clean hotel. I would recommend."
Ramesh 4-night trip
Posted 10 hours ago
The Royal Sonesta Chicago Downtown

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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