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 26 - Oct 27
Tomorrow
Oct 27 - Oct 28
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Crestwood hotels with a pool

A rooftop terrace with a glass floor, offering a view of the city skyline.
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
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.

1. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
Downtown Chicago
$144 nightly
$171 total
Nov 23 - Nov 24
Total with taxes and fees
Hotel Riu Plaza Chicago
An indoor swimming pool with clear lane markers, a tiled floor, and ceiling beams.
A banquet hall with round tables, chairs, and blue tablecloths.
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.
$114 nightly
$129 total
Nov 22 - Nov 23
Total with taxes and fees
DoubleTree by Hilton Chicago - Alsip
Pool
A grand ballroom with ornate chandeliers, a multi-tiered wedding cake centerpiece, and elegant floral arrangements on tables.
A multi-story building with a prominent entrance featuring a large archway and a sign.
A spacious lobby with a patterned carpet, seating area, and a fireplace.

3. Hilton Chicago

Hilton Chicago
Downtown Chicago
  • Soak in relaxation at this historic Chicago hotel's indoor pool with spa amenities nearby.
$162 nightly
$190 total
Nov 26 - Nov 27
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 bed, a desk, a television, a sofa, and a large window with a city view.
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.

4. 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 clear water, surrounded by lounge chairs and potted plants.
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.
A spacious restaurant with high ceilings, large windows, and a variety of seating arrangements including tables and chairs.

5. 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.
$122 nightly
$140 total
Nov 2 - Nov 3
Total with taxes and fees
Hilton Chicago/Oak Lawn
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 modern hotel lobby with a marble floor, a seating area with a bar, and a unique ceiling design.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.

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 Holiday Inn Express building with a covered entrance and a parking lot.
A modern dining area with a long table, blue chairs, and a coffee station.
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.
$101 nightly
$113 total
Nov 22 - Nov 23
Total with taxes and fees
Holiday Inn Express Crestwood by IHG
An indoor swimming pool with lounge chairs and tables, a tiled floor, and a ceiling with a unique light fixture.
A hotel reception area with a modern design, featuring a black reception desk, a 'Concierge' sign, and a 'Stairs' sign indicating the direction to the street level.
A multi-level hotel lobby with a central food service area, multiple dining tables, and a modern architectural design.
A multi-story building with a prominent curved glass facade, surrounded by other high-rise buildings.

8. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Downtown Chicago
  • Chicago hotel offers refreshing stays with indoor pool, fitness center, and walkable Michigan Avenue access.
$128 nightly
$170 total
Nov 24 - Nov 25
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
A swimming pool with a glass wall, a seating area with sofas, and an exit sign.
A multi-story hotel with a prominent 'Embassy Suites' sign, a Starbucks Coffee shop, and a well-lit street at night.
A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.
A spacious lobby with a central staircase, multiple floors, a reception desk, and seating areas.

9. 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.
$116 nightly
$158 total
Nov 24 - Nov 25
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North
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 bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

10. 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 24 - Nov 25
Total with taxes and fees
InterContinental Chicago Magnificent Mile by IHG
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"What a charming and beautiful hotel. The building needs some updating, however, it's a glorious and magnificent hotel."
Ben 1-night trip
Posted less than an hour ago
Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

8/10 Good
"Everyone so nice but long lines to check in."
Elvira 1-night trip
Posted 2 hours ago
Hilton Chicago
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

8/10 Good
"First the good: the location is great, right on the river and easily walkable to the Loop of the Magnificent Mile, etc. I arrived early and asked to check my bag, but my room was ready, which was nice. Somehow I got a fabulous upgrade to a comfortable spacious corner room on the 38th floor with the most spectacular views (views plural). When I returned later to rest before dinner, I couldn’t stop looking out the windows—what a show at sunset! The bed was very comfortable, although really really high off the ground. Everything seemed clean. Now the not-so-good: lighting was very sparse in the room—half the room had no lighting at all. No place to charge devices—hello, this is 2026. I had a little trouble with the temperature and there was no way to call downstairs—everything has to be handled in the app. So do stay here, but bring a charging station to plug into the wall—which is far from the bed."
LINDA 1-night trip
Posted 9 hours ago
The Royal Sonesta Chicago Downtown
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"I really enjoyed my stay here! One of the first things I noticed was how clean and well-kept everything was, which made me feel comfortable right away. The staff was amazing, always friendly, welcoming, and willing to help with anything I needed. I also really appreciated how convenient the location was. It made getting around so much easier. It's always nice to stay somewhere that feels comfortable and where you're treated well. I had a great experience overall and would definitely stay here again. Highly recommend!"
Jorje 1-night trip
Posted 21 hours ago
Fairmont Chicago at Millennium Park

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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