Westchester Holidays

    Plan, book, travel with confidence
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    Better together
    Save up to HK$890 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top Westchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Trump International Hotel & Tower Chicago
Level Chicago – Old Town
Park Hyatt Chicago
The Langham, Chicago

Top hotels in Westchester

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is HK$976 per night from 27 May to 28 May
HK$976
per night
27 May - 28 May
7.6/10 Good! (2,594 reviews)
"Very cozy"

Reviewed on 20 May 2024

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is HK$1,160 per night from 28 May to 29 May
HK$1,160
per night
28 May - 29 May
7.6/10 Good! (6,775 reviews)
Live History!
"Incredible building with such nostalgia and grace (definitely ask to check out the Gold Room on the second floor). Huge lofted rooms, with GREAT A/C and comfy beds! Wonderful location next to gorgeous parks, beautiful fountains, and a short walk to the lake. Close to the CSO, Art Institute, and sooooo ..."

Reviewed on 20 May 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is HK$1,253 per night from 27 May to 28 May
HK$1,253
per night
27 May - 28 May
8.6/10 Excellent! (2,888 reviews)
"Staff at the front desk are really helpful and friendly"

Reviewed on 19 May 2024

River Hotel
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.

Frequently asked questions

How much does a Westchester holiday package cost?
From just HK$3,711. Yes, you read that correctly. Our Westchester packages are a simple way to make your budget stretch further. Combine your flights, hotels and rental car and get to know this exciting destination.
How do I get a cheap travel package to Westchester?
Combine your flight and hotel bookings, throw in extras such as a rental car or activities, and save with a Westchester holiday package. You won’t just walk away with superb discounts on your escape — you’ll have loads of choice within your reach too. When you book through Expedia, you can choose from more than 550 air carriers and 1,000,000 hotels around the globe. Your affordable holiday begins right here, right now!
Where should I stay in Westchester?
A getaway to Westchester wouldn’t be complete without paying a visit to Brookfield Zoo, Oak Brook Golf Course and Galloping Ghost. Spend your evenings close to these top sights and make sightseeing simple.
What are the top hotels in Westchester?
When it comes to comfortable places to stay in Westchester, you can’t beat Four Points by Sheraton Chicago Westchester/Oak Brook. Browse our deals and pick up a bargain.
How far in advance should I book my Westchester holiday?
The earlier, the better. Airlines generally release flight tickets up to 12 months ahead of departure, and this is a great opportunity to land some of the lowest prices. Just been told you should take all your holiday days in a few weeks? No problem! Expedia are never short of fantastic bargains to whisk you away on the getaway of your dreams, at a price you can afford.
What does an Expedia Westchester travel package include?
Hotels, rental cars and flights — we have them covered. With Expedia, you can create your Westchester travel package just how you like it. All you have to do is decide just what you need. Once you’ve made your booking, you can add on fun things like activities and tours. The more you bundle, the more you save!
What should I know before booking a Westchester travel package?
When you book your hotels, flights and car rentals together, you’ll land amazing discounts. Whether you’re organising a mountain getaway in a cabin or want to stay in a luxurious city hotel, Expedia will make it happen for less.
Can I choose my airline with a Westchester Expedia holiday package?
With a holiday package, you’re in charge. Whether you’d prefer to fly to Westchester in coach or first class, simply select from the available airline options. Expedia has access to over 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Westchester holiday package?
It’s hard to predict what tomorrow might bring, so it’s comforting to know that you can change or cancel your Westchester holiday package. If your booking was made in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for more information.

Popular places to visit

What to do in Westchester

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.