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

Best Resorts in Crestwood

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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for Crestwood resorts

Couples treatment rooms, sauna, body treatments, aromatherapy

1. Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel
4.0 star property
East Hazel Crest
9.4 out of 10, Exceptional, (578 reviews)
"Fun place to stay"
United States
David
$199 nightly
The price is $222
Sep 1 - Sep 2
Total with taxes and fees
Wind Creek Southland Casino and Hotel
Golf

2. Hilton Chicago/Oak Brook Hills Resort & Conference Center

Hilton Chicago/Oak Brook Hills Resort & Conference Center
4.0 star property
Oak Brook
9.0 out of 10, Wonderful, (1,006 reviews)
"Great location and our room was perfect!"
United States
Elise
$145 nightly
The price is $161
Aug 9 - Aug 10
Total with taxes and fees
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Crestwood Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"We loved the rooftop bar. The bartender was great! The staff was friendly and allowed us to check in early at no additional cost."
Kassi 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection - Magnificent Mile

Find out more about Crestwood

Crestwood Resorts information

Number of reviews
1,584
Accommodation
2 Resorts
Lowest Price
$161
Highest Price
$222

Frequently asked questions

What is Crestwood like for a resort vacation?
You deserve some time off, and a resort is the perfect place to treat yourself to the services and amenities you need for a relaxing stay in Crestwood. One of the 5 comfortable resorts in the surrounding area might be just what you're searching for, whether you're hoping for great restaurants on site, a state-of-the-art fitness center, or nightly entertainment options.
What's a favorite resort for my stay in Crestwood?
Here are our top-rated resorts around Crestwood: Wind Creek Southland Casino and Hotel - Spa resort. 8.4 mi (13.5 km) from Crestwood. Features 4 restaurants, 3 bars, and a full-service spa. Hilton Chicago/Oak Brook Hills Resort & Conference Center - Spa resort. 15.8 mi (25.5 km) from Crestwood. Has 4 restaurants, 2 bars, and a golf course. Highly rated for its pool.
What can I do in Crestwood?
Travelers enjoy the shopping and other activities in Crestwood, and also have good things to say about the dining options here. Hollywood Park offers fun for the whole family, while Soldier Field is one of the most popular places to visit nearby. Other attractions in the area include Trinity Christian College and Gaelic Park.
What's the seasonal weather like in Crestwood?
The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. Average annual precipitation for Crestwood is 47 inches.
What's the best way to get to and around Crestwood?
Fly into Chicago Midway Airport (MDW), which is located 8.8 mi (14.2 km) from the heart of the city. Otherwise, look for flights into Chicago O'Hare Intl. Airport (ORD), which is 23.2 mi (37.3 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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