Cheap Flights to Westchester

View NZ$137 flight on Sat, 28 Feb 2026Opens in a new window

Popular airlines to Westchester

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 35% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

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
Sat, 28 Feb - Sat, 7 Mar
DFW
Dallas
ORD
Chicago
NZ$274 Return, found 1 day ago
NZ$274
Return
found 1 day ago
Select American Airlines flight, departing Sat, 28 Feb from Dallas to Chicago, returning Sat, 7 Mar, priced at NZ$274 found 1 day ago
Delta
Sat, 28 Feb - Sat, 7 Mar
DAL
Dallas
ORD
Chicago
NZ$308 Return, found 1 day ago
NZ$308
Return
found 1 day ago
Select Delta flight, departing Sat, 28 Feb from Dallas to Chicago, returning Sat, 7 Mar, priced at NZ$308 found 1 day ago
United
Sat, 28 Feb - Sat, 7 Mar
DFW
Dallas
ORD
Chicago
NZ$396 Return, found 1 day ago
NZ$396
Return
found 1 day ago
Select United flight, departing Sat, 28 Feb from Dallas to Chicago, returning Sat, 7 Mar, priced at NZ$396 found 1 day ago
Alaska Airlines
Thu, 16 Apr - Thu, 30 Apr
IAH
Houston
ORD
Chicago
NZ$554 Return, found 4 days ago
NZ$554
Return
found 4 days ago
Select Alaska Airlines flight, departing Thu, 16 Apr from Houston to Chicago, returning Thu, 30 Apr, priced at NZ$554 found 4 days ago
Icelandair
Sat, 21 Feb - Sat, 28 Feb
LHR
London
ORD
Chicago
NZ$869 Return, found 4 days ago
NZ$869
Return
found 4 days ago
Select Icelandair flight, departing Sat, 21 Feb from London to Chicago, returning Sat, 28 Feb, priced at NZ$869 found 4 days ago

Westchester Flights

The Westchester experience you’ve always wanted

Catching a flight to Westchester is easier than it’s ever been when you use Expedia to plan your escape. A great holiday starts with great selection, and we have an amazing amount of Westchester flight deals. A quick search on Expedia.co.nz will show you cheap tickets to Westchester in mere moments, from overnight flights to weekend getaways. Trying to earn frequent flyer points? We even make it easy for you to stay loyal to your preferred airline.

Been a while since you’ve travelled?

If you haven’t flown recently, you might like some insider information. In fact, even seasoned travellers should check out our blog. Featuring hundreds of articles written by our very own experts, our blog keeps you informed about all the fantastic attractions and things to do in the world’s most popular destinations, so you know just what to pack. Get ready for great advice on trip preparation and seeing the sights—then get ready to fly!

Bundle your room and flight to travel for less

Package your flights with your hotel booking in Westchester, and your trip will become even cheaper. By making all of your reservations with us, you’ll save money and time, plus have the peace of mind that comes with booking all of your arrangements in one place. It may seem like magic, but it’s just the Expedia.co.nz way.

A holiday at the tips of your fingers

Take the high-tech road when you use our Expedia app to plan your holiday to Westchester. Our handy app allows you to reserve flights and hotels at any time of day, on any type of phone, because it’s available on both Android and iOS. You’ll also benefit from exclusive deals, have a chance to earn extra points, and can keep your itinerary at your fingertips. No matter where you are, count on our app to help you get where you’re going.

Register for Frequent Flyer Rewards

If you enjoy being pampered every once in a while, register with our Expedia Rewards program to get exclusive offers and discounts you won’t find anywhere else. Expedia Rewards grants you member-only benefits, plus price guarantees on your room rates. We can even help you rack up frequent flyer points more quickly. Plus, by signing up, you can book our Unreal Deals, which, when bundled with your room, could save you the cost of a whole plane ticket.

Start planning and start packing

Expedia.co.nz makes it easy to find cheap flights to Westchester NZ$274. With such amazing deals, why wait any longer to book your trip? Start searching today, and we’ll see you soon in Westchester.

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.

Flights to Westchester information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
NZ$273

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 Canada
Fri, 13 Feb - Tue, 3 Mar
CHC
Christchurch
ORD
Chicago
NZ$1,359 Return, found 4 days ago
NZ$1,359
Return
found 4 days ago
Select Air Canada flight, departing Fri, 13 Feb from Christchurch to Chicago, returning Tue, 3 Mar, priced at NZ$1,359 found 4 days ago
*Available to Expedia members.