Find Luxury Hotels in Westchester, IL

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Check availability on Westchester Luxury Hotels

Tonight
Dec 22 - Dec 23
Tomorrow
Dec 23 - Dec 24
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Westchester luxury hotels

2 bars/lounges, rooftop bar
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1009)
"Great location and restaurant "
United Kingdom
Asvin
The price is NT$4,633
NT$6,365 total
includes taxes & fees
Jan 11 - 2026/1/12
theWit Chicago, a Hilton Hotel
Penthouse (Suite) | Egyptian cotton sheets, premium bedding, down comforters, minibar
Viceroy Chicago

Viceroy Chicago

Viceroy Chicago
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1144)
"Very nice hotel, great rooms, comfy bed and the staff were all very friendly."
United States
Randall
The price is NT$6,786
NT$8,893 total
includes taxes & fees
Jan 5 - 2026/1/6
Viceroy Chicago
55-inch LCD TV with cable channels, TV, pay movies
L7 Chicago by LOTTE

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3421)
"Enjoyed my stay"
United States
Karen
The price is NT$3,664
NT$4,302 total
includes taxes & fees
Dec 25 - Dec 26
L7 Chicago by LOTTE
Lunch and dinner served
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1794)
"Great hotel, close to shopping and restaurants, excellent customer service, highly recommend."
United States
Gina
The price is NT$4,215
NT$5,769 total
includes taxes & fees
Dec 23 - Dec 24
Radisson Blu Aqua Hotel Chicago
Front of property - evening/night
The Peninsula Chicago

The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1012)
"Best hotel in Chicago"
United States
Michael
The price is NT$14,992
NT$17,599 total
includes taxes & fees
Jan 4 - 2026/1/5
The Peninsula Chicago
Bar (on property)
Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1452)
"Gorgeous hotel and amazing staff"
Canada
Kristin
The price is NT$4,115
NT$4,831 total
includes taxes & fees
Dec 29 - Dec 30
Canopy by Hilton Chicago Central Loop
Breakfast and dinner served
Omni Chicago Hotel

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1657)
"Great place to stay "
United States
Juliet
The price is NT$5,025
NT$6,825 total
includes taxes & fees
Dec 23 - Dec 24
Omni Chicago Hotel
Indoor pool
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2642)
"Great stay"
United States
Rawleigh
The price is NT$4,640
NT$6,456 total
includes taxes & fees
Jan 20 - 2026/1/21
InterContinental Chicago Magnificent Mile by IHG
Exterior
Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1004)
"It was a wonderful stay! The staff is very friendly and helpful. I enjoyed how close we were to everything. It was the perfect place to stay for a Christmas trip of shopping, dining and seeing a show."
United States
Dawn
The price is NT$3,945
NT$5,556 total
includes taxes & fees
Dec 29 - Dec 30
Hotel Chicago Downtown, Autograph Collection by Marriott
2 restaurants, breakfast, lunch, dinner served; American cuisine
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3466)
"Great hotel! "
United States
Kianna
The price is NT$4,115
NT$4,831 total
includes taxes & fees
Jan 4 - 2026/1/5
LondonHouse Chicago, Curio Collection by Hilton
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.
View all properties

Top Westchester Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Staff very friendly"
Kara 1-night trip
Posted 6 hours ago
Hilton Chicago

Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in Westchester?
Use Expedia to arrange your flight to Chicago Midway Airport (MDW) airport or Chicago O'Hare Intl. Airport (ORD) airport, and then choose from a variety of places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you'd like to make your stay special. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Westchester offers. During your visit, you might want to enjoy the restaurants which Westchester is known for.
When can I expect good weather in Westchester?
Planning for the weather is an important factor for making your trip to Westchester a success, especially when you're splurging. 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 there to see and do in Westchester?
Enjoy Westchester and visit Wrigley Field, Michigan Avenue, and United Center. If you have a little extra time during your trip, you might want to make a stop at Soldier Field and Navy Pier.

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