Cheap Flights to Westchester

View AU$108 flight on Wed, 31 Dec 2025Opens in a new window

Popular airlines to Westchester

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Cheap Tickets to Westchester

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, 5 Nov - Wed, 12 Nov
DFW
Dallas
ORD
Chicago
AU$240 Return, found 3 days ago
AU$240
Return
found 3 days ago
Select American Airlines flight, departing Wed, 5 Nov from Dallas to Chicago, returning Wed, 12 Nov, priced at AU$240 found 3 days ago
Delta
Mon, 3 Nov - Tue, 11 Nov
DAL
Dallas
ORD
Chicago
AU$299 Return, found 6 days ago
AU$299
Return
found 6 days ago
Select Delta flight, departing Mon, 3 Nov from Dallas to Chicago, returning Tue, 11 Nov, priced at AU$299 found 6 days ago
Alaska Airlines
Sat, 15 Nov - Sat, 6 Dec
LAX
Los Angeles
ORD
Chicago
AU$330 Return, found 1 day ago
AU$330
Return
found 1 day ago
Select Alaska Airlines flight, departing Sat, 15 Nov from Los Angeles to Chicago, returning Sat, 6 Dec, priced at AU$330 found 1 day ago
Hawaiian Airlines
Tue, 18 Nov - Sat, 6 Dec
LAX
Los Angeles
ORD
Chicago
AU$330 Return, found 1 day ago
AU$330
Return
found 1 day ago
Select Hawaiian Airlines flight, departing Tue, 18 Nov from Los Angeles to Chicago, returning Sat, 6 Dec, priced at AU$330 found 1 day ago
United
Thu, 27 Nov - Thu, 4 Dec
AUS
Austin
ORD
Chicago
AU$371 Return, found 14 hours ago
AU$371
Return
found 14 hours ago
Select United flight, departing Thu, 27 Nov from Austin to Chicago, returning Thu, 4 Dec, priced at AU$371 found 14 hours ago

Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD)

July is typically the cheapest month to fly

From AU$116 - AU$398 per traveller.

Frequently asked questions

What is the name of Westchester's airport?
Many visitors like to fly into O'Hare Intl. Airport (ORD) when visiting the lively city of Westchester.
How far is ORD from central Westchester?
ORD is 14 kilometres from downtown Westchester, so be prepared for a reasonable commute into the heart of the city.
What airport is best to fly into Westchester?
If you're planning on jumping on a plane to Westchester, you'll probably land at O'Hare Intl. Airport (ORD) (14 kilometres from downtown). Midway Intl. Airport (MDW) (13 kilometres from downtown) is the other major airport that services the city.
How many airlines fly to Westchester?
There are a total of 51 air carriers connecting Westchester to 237 airports across the globe.
Which airlines fly to Westchester?
United Airlines, American Airlines and Delta fly the most frequently to Westchester. The majority of these flights arrive here from New York, with United Airlines offering the most services on this route.
How many nonstop flights are there to Westchester?
Flying to a new place is much more straightforward when there aren't any stopovers involved. If you're off to Westchester, the fantastic news is that there are approximately 7,564 direct flights every week.
Where are the most popular flights to Westchester departing from?
The most popular flights to Westchester leave from New York, Washington and Dallas airports.
How long is the flight to Westchester Airport?
Where you depart from determines how much of the in-flight entertainment you'll get to enjoy. From New York to Westchester, the average flight time is 2 hours and 44 minutes. From Washington it's around 2 hours and 15 minutes, and from Dallas it's 2 hours and 18 minutes.
How to book the cheapest flight to Westchester?
Don't leave booking your flight to Westchester until the last minute. That's one trick frequent travellers use to get the best deals. Booking ahead means more options and cheaper flights. Don't stop there, though. Do some research and find out if there is more than one airport at your destination. Ticket prices often differ depending on which airport you use. Don't forget to compare fares across air carriers as well. Finally, be ready to lock in your seat quickly if you stumble on a great price. It might not be available for long! With a bit of knowledge and some luck, the perfect airfare can be yours.
Do you have any tips for my flight to Westchester?
If you're poorly prepared, travelling can be testing. But don't hit the panic button just yet. Follow these handy tips and enjoy a comfortable start to your time in Westchester. What to pack in your hand luggage:

  • A plane ride can be a stress-free experience if you take the right stuff. Firstly, you'll need toiletry items, such as a toothbrush and some deodorant, a clean set of clothes and a good book. Secondly, make room in your hand luggage for your laptop, a charger, your medications and maybe a blow-up neck pillow as well. Lastly, and most importantly, don't forget to bring your passport, travel papers and some cash.

Do not pack the following items in your hand luggage:

  • Pack all your full-sized bottles of shampoo and conditioner in your checked baggage. Any liquids or gels in your carry-on bag larger than 3.4 ounces (100 millilitres) won't be allowed on. Sharp objects, like your beloved pocket knife, and dangerous products which are flammable or explosive, such as aerosols and matches, are also banned.

What to wear on a flight:

  • Your aim is to be as comfortable as you can. Choose flat, closed-toe shoes, dress in loose, natural-fibre clothing and remember to bring a jacket in case you get cold in the cabin.
  • Most travellers have heard about deep vein thrombosis (DVT), a blood clot condition caused by long periods of inactivity. To minimize your risk on board, drink lots of water, consider wearing compression tights or socks and move your lower limbs often.

How to get through airport security fast when flying to Westchester?
It's simple — be prepared. We've put together some handy tips and tricks for a fuss-free trip through airport security. Watch out Westchester, here you come:

  • Airport security personnel first need to check that you have a valid ID and matching travel documents before anything else. Have them close by, ready for inspection.
  • Next up is the X-ray machine. Empty your pockets and remove anything metal that is likely to set off the scanner's alarm. This includes items like earphones or headphones, as well as heavy coats or jackets. They'll need to be placed on the conveyor belt for screening.
  • For just a few moments, you'll need to unplug from technology. Your phone, laptop and any other electronics also need to be sent through the scanner.
  • Remove all liquids and gels from your carry-on bag. They often need to be sent through the X-ray scanner separately. Each product should be no larger than 3.4 ounces (100 millilitres) and everything must fit in a single quart-size (one litre), clear zip-close bag.
  • Lightweight sneakers are a clever footwear choice as you're less likely to be required to remove them when going through security. Hiking boots and other heavy-style shoes are often subjected to additional screening.
  • Pocket knives and other sharp items are not allowed in the cabin. They'll be seized at security, so pack them safely away in your checked bags.

Book with confidence

Westchester Flights

Have the time of your life in Westchester

Flying to Westchester is now easier than ever when you use Expedia to book your trip. We’ve got an extensive catalogue of Westchester flight deals, giving you the greatest number of options to choose from. Whether you prefer to fly on weekdays or weekends, in the morning or at night, a quick search on Expedia.com.au will help you find cheap tickets to Westchester in seconds. We even make it simple for you to stick with a certain airline if you’re trying to rack up frequent flyer points.

Tips for flying and packing light

If it’s been a while since you’ve travelled, you might be due for a refresher when it comes to flying. That’s where our helpful blog, Out There Starts Here, comes in. Wondering whether to pack for fine dining or more casual eats? Or whether you really need to bring a jacket? Written by seasoned travel experts, the articles on our blog provide you with the latest details about certain destinations, so you know just what to expect. Check out some of our recent articles for the smartest ways to see the sights.

Fly for less when you bundle airfare and accommodation

Our already low airfares are even more affordable when you bundle your flights with a stay at one of the hotels in Westchester. By booking all of your travel plans with us, you’ll save time and money, and enjoy the convenience of having all of your arrangements in one place.

Get the power of planning in the palm of your hand

Booking your trip to Westchester, Chicago has never been easier than when you use our mobile app to plan your dream getaway. The Expedia App is available on both Android and iOS, allowing you to reserve flights and hotels at any time of day, no matter what kind of phone you use. You’ll also get exclusive offers, receive flight updates, and can earn extra points. Wherever you are, the Expedia App helps you get where you want to be.

Join the Expedia Rewards Program

If you enjoy the finer things in life, sign up for our rewards program to receive exclusive benefits when you book with us. Expedia Rewards opens the door to member-only deals, +VIP Access hotel benefits, and earning Expedia Rewards points, that you can redeem your way. You’ll also get access to Unreal Deals that could save you the price of a plane ticket to Westchester when bundled with your accommodation.

What are you waiting for?

Expedia.com.au helps you find cheap flights to Westchester AU$240. So why wait another second to begin planning your trip? Start your search right now, and you could be boarding the next Westchester-bound flight. Bon voyage!

Westchester Flights

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
AU$1,549

Trending flights to Westchester

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air New Zealand
Sat, 8 Nov - Sat, 15 Nov
SYD
Sydney
ORD
Chicago
AU$1,562 Return, found 1 hour ago
AU$1,562
Return
found 1 hour ago
Select Air New Zealand flight, departing Sat, 8 Nov from Sydney to Chicago, returning Sat, 15 Nov, priced at AU$1,562 found 1 hour ago

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