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 23 - Oct 24
Tomorrow
Oct 24 - Oct 25
This weekend
Oct 23 - Oct 25
Next weekend
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 couple dining at a table with a city view, surrounded by chairs and a variety of dishes.
A spacious lobby with a marble floor, a reception desk, and a glass partition.

1. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
Downtown Chicago
$136 nightly
$161 total
Nov 22 - Nov 23
Total with taxes and fees
Hotel Riu Plaza Chicago
An indoor swimming pool with clear lane markers, a tiled floor, and ceiling beams.
A spacious lobby with a central seating area, a reception desk, and a modern chandelier.
An outdoor dining area with brick walls, string lights, and tables set for guests.
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.
$114 nightly
$129 total
Nov 22 - Nov 23
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 restaurant with high ceilings, large windows, and a variety of seating arrangements including tables and chairs.
A spacious indoor area with a long table, multiple chairs, a sofa, and several gaming machines.

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 grand ballroom with ornate chandeliers, a multi-tiered wedding cake centerpiece, and elegant floral arrangements on tables.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
A spacious hotel lobby with a large seating area, a flat-screen TV, and a view of the ocean.

4. Hilton Chicago

Hilton Chicago
Downtown Chicago
  • Soak in relaxation at this historic Chicago hotel's indoor pool with spa amenities nearby.
$160 nightly
$190 total
Nov 22 - Nov 23
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 hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.
A cityscape at dusk with high-rise buildings, including a Hilton hotel.
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
$118 nightly
$140 total
Nov 23 - Nov 24
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 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.
A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

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.
$119 nightly
$141 total
Nov 23 - Nov 24
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 lobby with a reception desk, a sofa, and large windows offering a view of the outside.

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.
$95 nightly
$106 total
Nov 22 - Nov 23
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.
The Intercontinental hotel facade with a large American flag and a floral display.
A person sitting by a window with a cityscape view.
A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.

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.
$212 nightly
$253 total
Nov 22 - Nov 23
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.
A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.
Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.

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.
$101 nightly
$120 total
Nov 23 - Nov 24
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 multi-level indoor area with a central water feature, surrounded by seating areas and greenery.
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.

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.
$127 nightly
$151 total
Nov 22 - Nov 23
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North
View all properties

Choose what matters most at hotels with a pool in Crestwood

Breakfast included
Hot tub
4 stars
5 stars
Spa

Find out more about Crestwood

Discover top Crestwood attractions

Crestwood offers a delightful blend of outdoor adventures and cultural experiences that will captivate any traveler. Nature enthusiasts will love the scenic trails winding through lush landscapes, perfect for leisurely walks or invigorating hikes. For those interested in history, the local heritage sites provide insight into the area’s fascinating past, showcasing well-preserved architecture and rich stories that unfold at every turn. Families can enjoy a day of exploration at charming parks, where kids can play and adults can relax in beautifully maintained green spaces. Art lovers will appreciate the vibrant local art scene, with galleries showcasing a variety of styles and mediums, offering a glimpse into the creative spirit of the community. After a day filled with activities, unwind in one of Crestwood’s inviting accommodations that prioritize comfort and service, ensuring you feel pampered during your stay. Whether you’re seeking adventure or relaxation, Crestwood has something special for everyone.

Find the best pool hotels in Crestwood

For travelers seeking a refreshing escape with pool amenities, Crestwood offers some inviting hotel options. Each of these properties features indoor pool facilities perfect for relaxation and fun.

Holiday Inn Express Crestwood by IHG

  • Why it's great: The Holiday Inn Express Crestwood by IHG is an ideal choice for travelers looking to enjoy a refreshing indoor pool experience. With a solid traveler review rating of 8 out of 10, this budget-friendly hotel ensures a comfortable stay with features designed for relaxation and enjoyment. Guests can make a splash in the indoor pool, making it perfect for both leisure and exercise. In addition to the inviting pool, travelers will appreciate the complimentary buffet breakfast that starts the day off right. The hotel offers free WiFi and self-parking, adding convenience to your stay. For those needing extra space, connecting rooms and sofa beds are available. The hotel is also LGBTQIA welcoming, ensuring an inclusive atmosphere. Daily housekeeping helps maintain a clean and pleasant environment, while microwaves in the rooms provide added convenience for snack preparation.
  • Nearby attractions: Metrosouth Medical Center - 5 miles, Bremen Grove Dog Park - 5 miles

Top Crestwood Hotel Reviews

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Just wish the restaurant hours were a little later"
Marianna 6-night trip
Posted 12 hours ago
Eurostars Magnificent Mile
Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"Historic hotel that has some upgrades and modern amenities. The lobby bar could use some upgrades and a second working elevator on the South tower would have been helpful on busy days."
Marc 2-night trip
Posted 13 hours ago
Congress Plaza Hotel

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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