Westchester Holidays from AU$3,823

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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

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
6 Jun - 9 Jun
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Every single person working at this facility was extremely polite and welcoming. I’ve stayed in so many hotels across the world and I have to say this was the best experience I’ve ever had staying at a hotel. Ordered food at 3am and it was fantastic. My cloths got folded in the short period of time my wife and I left the room and came back to a spotless room. Overall amazing experience. Will be staying here every time I come to Chicago.

Reviewed on 16 Apr. 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
6 Jun - 9 Jun
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (650 reviews)
Centrally located and easy access to most of the places, lots of restaurants and lively place

Reviewed on 17 Apr. 2024

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
6 Jun - 9 Jun
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (1,009 reviews)
The staff was super friendly! I would go back in a heartbeat.

Reviewed on 17 Apr. 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
6 Jun - 9 Jun
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.6/10 Exceptional! (965 reviews)
Friendly and helpful staff, super comfy rooms and bed! Walked everywhere- easy walk to museum/aquarium, shopping, dining etc. will definitely be back!

Reviewed on 15 Apr. 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
6 Jun - 9 Jun
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (3,485 reviews)
Very nice staff and great customer service! Would highly recommend the hotel bar, as the drinks and food were delicious! Only issue is that the deposit fee was not returned.

Reviewed on 18 Apr. 2024

Prices and availability subject to change. Additional terms may apply.

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

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$206 per night from 28 Apr to 29 Apr
AU$206
per night
28 Apr - 29 Apr
7.6/10 Good! (6,544 reviews)
"I really enjoyed our view of the lake."

Reviewed on 16 Apr. 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$223 per night from 21 Apr to 22 Apr
AU$223
per night
21 Apr - 22 Apr
8.6/10 Excellent! (2,777 reviews)
"The front staff is amazing, had a last minute change of mind about the room I book and they upgraded us on spot. Everyone there is amazing and very helpful! The hotel its self is at a prime location and only a few minutes walk away from the attractions in Chicago. The valet service was good and very ..."

Reviewed on 17 Apr. 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$274 per night from 23 Apr to 24 Apr
AU$274
per night
23 Apr - 24 Apr
8.2/10 Very Good! (1,849 reviews)
"Property was very nice"

Reviewed on 18 Apr. 2024

Eurostars Magnificent Mile
See all 4,640 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$3,823. 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
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.