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Cheap Flights to Westchester: Westchester Flight Deals

View €77 flight on Sat, 17 Oct 2026Opens in a new window

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Cheap round-trip flights to Westchester

Prices were available within the past 7 days and start at €77 for one-way flights and €118 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Aer Lingus
American Airlines
Delta
United
Southwest Airlines

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

From €79 - €102 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

Expedia.ie is an online travel company that specialises in securing the best prices for flights to Westchester. With Expedia you get highly specialised services, combining the best of technology, in-depth knowledge and the best connections in order to offer great deals to Westchester. Expedia shares your passion for travel and has built the best online travel service that promotes and encourages travel. Whether you are looking for cheap flights to Westchester, or are just on the lookout for the best flights to Westchester, you are sure to find the best deals with Expedia.ie.

"One of the many benefits of booking your flights through Expedia is that we are one of the world’s largest online travel agency, which means we use our collective experience and work tirelessly to bring you the best prices. With Expedia you get a user-friendly internet experience and a dedicated customer support service that ensures that everything goes smoothly. The goal of Expedia is to offer premium services at the lowest price, all at one single place. If you wish to save even more try combing a hotel in Westchester to your flight and create a personalised low cost city break or holiday to your favourite destination. Book early and you could save even more!

If you have an Expedia.ie itinerary number and have a question or concern about your travel plans you can call us on (01) 524 5005 from 8am - 10pm Monday to Friday, and 9am - 10pm at weekends and an Expedia agent will help you.

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
€118

Trending flights to Westchester

Prices were available within the past 7 days and start at €77 for one-way flights and €118 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Aer Lingus
*Available to Expedia members.