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Best Resorts in Westchester

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Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Our top choices for Westchester resorts

A large hotel with a central courtyard, a lake, and a bridge.

1. 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, (1,002 reviews)
"Good place to stay"
Canada
MARGOT CAROLE BOGNI
$137 nightly
The price is $152
Nov 1 - Nov 2
Total with taxes and fees
Hilton Chicago/Oak Brook Hills Resort & Conference Center
A patio area with outdoor seating, a fire pit, and a view of a golf course.

2. Eaglewood Resort and Spa

Eaglewood Resort and Spa
4.0 star property
Itasca
8.8 out of 10, Excellent, (1,363 reviews)
"The breakfast is good here, and the golf course is well maintained."
United States
David
$159 nightly
The price is $177
Oct 4 - Oct 5
Total with taxes and fees
Eaglewood Resort and Spa
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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"The room was very spacious. The location of the hotel was great. The breakfast was delicious. We will definitely stay here again!"
Samantha 1-night trip
Posted 3 hours ago
The Chicago Hotel Collection - Magnificent Mile

Find out more about Westchester

Westchester Resorts information

Number of reviews
Accommodation
2 Resorts
Lowest Price
$152
Highest Price
$177

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 6 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: Eaglewood Resort and Spa - Spa resort. 11.1 mi (17.8 km) from Westchester. Features 2 restaurants, 2 bars, and a golf course. Hilton Chicago/Oak Brook Hills Resort & Conference Center - Spa resort. 5.1 mi (8.2 km) from Westchester. Has 4 restaurants, 2 bars, and a golf course. Highly rated for its pool.
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 Soldier Field and Navy Pier 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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