Best Resorts in Westchester

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Check prices for these dates

Next weekend
Apr 3 - Apr 5
In two weeks
Apr 10 - Apr 12
In one month
Apr 24 - Apr 26
In two months
May 22 - May 24

Our top choices for Westchester resorts

Exterior

Eaglewood Resort and Spa

Eaglewood Resort and Spa
4.0 star property
Itasca
8.8 out of 10, Excellent, (1,000 reviews)
"Great resort and even better staff."
United States
Carlos
$126 nightly
The price is $140
Apr 5 - Apr 6
Total with taxes and fees
Eaglewood Resort and Spa
Golf

Hilton Chicago/Oak Brook Hills Resort & Conference Center

Hilton Chicago/Oak Brook Hills Resort & Conference Center
4.0 star property
Oak Brook
8.8 out of 10, Excellent, (1,002 reviews)
"Really good service "
United Kingdom
Milan
$147 nightly
The price is $164
Apr 2 - Apr 3
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 Westchester Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Breakfast terrific. Good location. Staff is very professional. Very nice."
Joseph 4-night trip
Posted 1 hour ago
Hotel Riu Plaza Chicago

Find out more about Westchester

Westchester Resorts information

Number of reviews
2,002
Accommodation
2 Resorts
Lowest Price
$140
Highest Price
$164

Frequently asked questions

What can I expect from a resort vacation in Westchester?
Longing for a relaxing getaway? Treat yourself to the luxuries and comforts of a resort, where you can find everything you need for your vacation from convenient food and drink options to activities and entertainment. There are 5 resorts in the area, giving you a variety of options that might have the great restaurants or blissful spa treatments you're looking for.
What's the best resort for my stay in Westchester?
Here are our top-rated resorts around Westchester: Hilton Chicago/Oak Brook Hills Resort & Conference Center - Spa resort. 5.1 mi (8.2 km) from Westchester. Features 4 restaurants, 2 bars, and a golf course. Highly rated for its pool. Eaglewood Resort and Spa - Spa resort. 11.1 mi (17.8 km) from Westchester. Has 2 restaurants, 2 bars, and a golf course.
What can I do in Westchester?
Travelers enjoy the shopping and other activities in Westchester, and also have good things to say about the dining options here. Galloping Ghost offers fun for the whole family, while Wrigley Field is one of the most popular places to visit nearby. You'll also find top attractions like Michigan Avenue and United Center in the area.
What's the seasonal weather like in Westchester?
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. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What's the best way to get to and around Westchester?
Fly into Chicago Midway Airport (MDW), which is located 8.4 mi (13.4 km) from the city center. Otherwise, you can search for flights to Chicago O'Hare Intl. Airport (ORD), which is 8.9 mi (14.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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