Westchester Holidays from AU$922

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Your Westchester Holiday

Book a tailored Westchester holiday package that includes everything you need and nothing you don't. Good for nightlife, bars and pubs and cafes, consider staying in the neighbourhood of Wicker Park. Any trip to Westchester needs a well-planned itinerary. Fill yours with leading attractions like Brookfield Zoo, Oakbrook Centre Mall and Ernest Hemingway Museum and House. Your dream Westchester holiday is only clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored to suit your travel style.

The Latest Westchester Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

3.5 out of 5
Downtown Chicago
per person
26 Jul - 29 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,011 reviews)
The location was really close to the places I wanted to see while I was in town. The staff was really accommodating and helpful. The restaurant connected to hote was really good and convenient before we had to drive back to airport. Even though i didn’t want to pay for $60 valet, it was really easy when I needed the car to take a drive. I also didn’t like the rooms windows, seems they are single pane and you get a lot of outdoor noise at night.

Reviewed on 1 May 2024

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
per person
26 Jul - 29 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The staff were welcoming, courteous, and friendly. The location was perfect and room was beautiful and clean!

Reviewed on 14 Apr. 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
26 Jul - 29 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Little disappointed there was no free breakfast

Reviewed on 1 May 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
26 Jul - 29 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (206 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on 16 Mar. 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
26 Jul - 29 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (3,485 reviews)
Right in the core if you are travelling to Chicago for the first time, easy to get too from the airport even from train, staff welcoming and friendly - amazing service from Allen who took care of us and our bags, welcoming and caring. Definitely would pick this hotel again when visiting Chicago!

Reviewed on 2 May 2024

Westchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
16,700
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Rosemont Theatre, Brookfield Zoo and Parkway Bank Park Entertainment District

Our pick of the best Westchester Hotel Deals

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 AU$252 per night from 15 May to 16 May
AU$252
per night
15 May - 16 May
7.6/10 Good! (2,542 reviews)
"Its was a nice stay."

Reviewed on 30 Apr. 2024

Warwick Allerton - Chicago
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 AU$271 per night from 13 May to 14 May
AU$271
per night
13 May - 14 May
7.6/10 Good! (6,629 reviews)
"I like the Congress Plaza because it's still a reasonably priced downtown hotel that is close to a lot of downtown attractions. I didn't find the counter staff particularly professional, friendly, or helpful this particular visit. Was a bit disappointed by that. Otherwise, we liked our rooms (539 ..."

Reviewed on 1 May 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 AU$289 per night from 12 May to 13 May
AU$289
per night
12 May - 13 May
8.6/10 Excellent! (2,834 reviews)
"Loved the free water. Hotel staff (Pedro) was very friendly & helpful! The room was the perfect size for one person."

Reviewed on 30 Apr. 2024

River Hotel
See all 4,647 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
beach holidays

Beach Holidays

Beach Holidays
family friendly holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Westchester holiday package cost?
From just AU$922. 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.

Discover the most popular places to visit in Westchester

Image for Wrigley Field

Wrigley Field

4.5/5(21 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
Image for McCormick Place

McCormick Place

4.5/5(21 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
Image for Navy Pier

Navy Pier

4.5/5(64 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier

What to do in Westchester

Image for Chicago Pizza Tour

Chicago Pizza Tour

AU$113
Per adult
100% of travellers recommend
Chicago Pizza Tour
Image for Chicago Museum of Contemporary Art: General Admission Ticket

Chicago Museum of Contemporary Art: General Admission Ticket

AU$33
Per adult
90% of travellers recommend
Chicago Museum of Contemporary Art: General Admission Ticket
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.