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Check availability on Westchester Luxury Hotels

Our top choices for Westchester luxury hotels

Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,407 reviews)
"Great stay! I will stay here again on my next trip back this summer!"
United States
Letisha
The price is NT$4,642
NT$6,540 total
includes taxes & fees
Mar 24 - Mar 25
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,853 reviews)
"Great hotel"
United States
Mark
The price is NT$11,887
NT$13,954 total
includes taxes & fees
Mar 23 - Mar 24
Trump International Hotel & Tower Chicago
Lobby

The LaSalle Chicago, Autograph Collection by Marriott

The LaSalle Chicago, Autograph Collection by Marriott
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (338 reviews)
"Very nice place to stay : )"
United States
Andrea
The price is NT$6,793
NT$7,974 total
includes taxes & fees
Apr 3 - Apr 4
The LaSalle Chicago, Autograph Collection by Marriott
2 bars/lounges

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,004 reviews)
"The room had a great view of downtown and was very clean. The staff was friendly and the pool was nice. "
United States
Samantha
The price is NT$5,864
NT$7,844 total
includes taxes & fees
Apr 3 - Apr 4
Renaissance Chicago Downtown Hotel
Suite, 2 Bedrooms, Terrace (Lakeshore) | Lake view

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,003 reviews)
"staff was great /rooms were clean /Great location "
United States
peggy
The price is NT$12,656
NT$14,857 total
includes taxes & fees
Apr 1 - Apr 2
Four Seasons Hotel Chicago
Presidential Suite, 1 King Bed | Bathroom | Separate tub and shower, designer toiletries, hair dryer, bathrobes

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,341 reviews)
"Very nice hotel. Great accommodations, delicious restaurant and clean. Will stay here again! Rooms are on the smaller side but enough for what we needed and it was nice to have a view from top floor! "
United States
Jon
The price is NT$6,599
NT$8,686 total
includes taxes & fees
Mar 29 - Mar 30
Sofitel Chicago Magnificent Mile
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,475 reviews)
"Great stay! Wonderful location!"
United States
Renae
The price is NT$4,739
NT$6,691 total
includes taxes & fees
Apr 5 - Apr 6
Hyatt Regency Chicago
Lounge

Pendry Chicago

Pendry Chicago
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,131 reviews)
"Great location, clean and very nice restaurant and bar. "
United States
karina
The price is NT$6,088
NT$8,463 total
includes taxes & fees
Apr 12 - Apr 13
Pendry Chicago
55-inch LCD TV with cable channels, TV, pay movies

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3,781 reviews)
"Amazing hotel-- Loved staying here."
United States
Maureen
The price is NT$4,905
NT$5,758 total
includes taxes & fees
Mar 31 - Apr 1
L7 Chicago by LOTTE
Indoor pool

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,876 reviews)
"Staff was very nice, rooms were clean, and location was next to everything we needed. "
United States
Keith
The price is NT$5,703
NT$7,720 total
includes taxes & fees
Mar 22 - Mar 23
InterContinental Chicago Magnificent Mile by IHG
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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Wonderful hotel"
Ana Lucia 4-night trip
Posted 1 hour 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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