Cheap Flights to Westchester

View ₩81,500 flight on Tue, Nov 4, 2025Opens in a new window

Popular airlines to Westchester

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How much is the cheapest flight to Westchester?

Prices were available within the past 7 days and start at ₩81,500 for one-way flights and ₩176,700 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Oct 29 - Sat, Nov 15
BOS
Boston
ORD
Chicago
₩176,700 Roundtrip, found 1 day ago
₩176,700
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 29 from Boston to Chicago, returning Sat, Nov 15, priced at ₩176,700 found 1 day ago
American Airlines
Wed, Oct 1 - Sun, Oct 19
BOS
Boston
ORD
Chicago
₩260,000 Roundtrip, found 1 day ago
₩260,000
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Oct 1 from Boston to Chicago, returning Sun, Oct 19, priced at ₩260,000 found 1 day ago
United
Fri, Oct 3 - Sun, Oct 19
BOS
Boston
ORD
Chicago
₩260,000 Roundtrip, found 1 day ago
₩260,000
Roundtrip
found 1 day ago
Select United flight, departing Fri, Oct 3 from Boston to Chicago, returning Sun, Oct 19, priced at ₩260,000 found 1 day ago
Scandinavian Airlines
Wed, Oct 29 - Sun, Nov 2
BUD
Budapest
ORD
Chicago
₩749,900 Roundtrip, found 1 day ago
₩749,900
Roundtrip
found 1 day ago
Select Scandinavian Airlines flight, departing Wed, Oct 29 from Budapest to Chicago, returning Sun, Nov 2, priced at ₩749,900 found 1 day ago
Alaska Airlines
Thu, Sep 25 - Sat, Oct 4
ICN
Seoul
ORD
Chicago
₩832,300 Roundtrip, found 3 hours ago
₩832,300
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Thu, Sep 25 from Seoul to Chicago, returning Sat, Oct 4, priced at ₩832,300 found 3 hours ago

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

July is typically the cheapest month to fly

From ₩106,834 - ₩363,581 per traveler.

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 kilometers 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 kilometers from downtown). Midway Intl. Airport (MDW) (13 kilometers 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 travelers 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, traveling 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 milliliters) 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-fiber clothing and remember to bring a jacket in case you get cold in the cabin.
  • Most travelers 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 milliliters) and everything must fit in a single quart-size (one liter), 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

Book with confidence

Searching for cheap flights to Westchester? No travel company presents more choices than Expedia if you're looking to compare flights to Westchester. With more airlines, cheaper flights, fewer stops, and more departure and arrival times travellers should ensure they search on Expedia before any holiday to Chicago. Expedia provides the cheapest flights to many destinations in Chicago and you may find even greater savings if you combine your flight with a hotel stay in Westchester.

Travel information

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
₩176,700

Trending flights to Westchester

Prices were available within the past 7 days and start at ₩81,500 for one-way flights and ₩176,700 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, Sep 22 - Tue, Sep 23
ICN
Seoul
ORD
Chicago
₩798,500 Roundtrip, just found
₩798,500
Roundtrip
just found
Select American Airlines flight, departing Mon, Sep 22 from Seoul to Chicago, returning Tue, Sep 23, priced at ₩798,500 just found

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