Westchester Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Westchester

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$159 per night from 8 Dec to 9 Dec
S$159
includes taxes & fees
8 Dec - 9 Dec
7.8/10 Good! (8,182 reviews)
"Overall we liked the room we stayed at the only complaint was that the hallway leading to the room had an awful smell like lake dead fish or something when we arrived on 11/23 this morning the smell was less but it still smelled"

Reviewed on 25 Nov,2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$164 per night from 26 Dec to 27 Dec
S$164
includes taxes & fees
26 Dec - 27 Dec
8.6/10 Excellent! (3,551 reviews)
"Is very close to everything"

Reviewed on 23 Nov,2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$152 per night from 26 Dec to 27 Dec
S$152
includes taxes & fees
26 Dec - 27 Dec
8.4/10 Very Good! (3,272 reviews)
"It was a great experience"

Reviewed on 24 Nov,2024

Club Quarters Hotel, Central Loop, Chicago
See all 4,595 properties in Westchester
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 . 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

McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Westchester

Flyover in Chicago

Flyover in Chicago

S$51
Per adult
94% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

S$65
Per adult
94% of travellers recommend
Architecture River Tour
Narrated by certified, local docent

Chicago Architecture Center River Cruise aboard Chicago's First Lady

S$73
Per adult
96% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
See all activities in Westchester

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.