Cheap Flights to Westchester , IL from CA $159

View CA $159 flight on Mon, Apr 27, 2026Opens 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 CA $159 for one-way flights and CA $280 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Fri, May 1 - Tue, May 5
YUL
Montreal
ORD
Chicago
CA $282 Roundtrip, just found
CA $282
Roundtrip
just found
Select Air Canada flight, departing Fri, May 1 from Montreal to Chicago, returning Tue, May 5, priced at CA $282 just found
American Airlines
Fri, Apr 17 - Sun, Apr 19
YUL
Montreal
ORD
Chicago
CA $282 Roundtrip, just found
CA $282
Roundtrip
just found
Select American Airlines flight, departing Fri, Apr 17 from Montreal to Chicago, returning Sun, Apr 19, priced at CA $282 just found
WestJet
Sun, Apr 26 - Mon, Apr 27
YXX
Abbotsford
ORD
Chicago
CA $290 Roundtrip, found 2 days ago
CA $290
Roundtrip
found 2 days ago
Select WestJet flight, departing Sun, Apr 26 from Abbotsford to Chicago, returning Mon, Apr 27, priced at CA $290 found 2 days ago
United
Sat, Apr 11 - Tue, Apr 21
YUL
Montreal
ORD
Chicago
CA $295 Roundtrip, found 4 days ago
CA $295
Roundtrip
found 4 days ago
Select United flight, departing Sat, Apr 11 from Montreal to Chicago, returning Tue, Apr 21, priced at CA $295 found 4 days ago
Delta
Wed, Apr 29 - Fri, May 1
YUL
Montreal
ORD
Chicago
CA $298 Roundtrip, found 1 day ago
CA $298
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Apr 29 from Montreal to Chicago, returning Fri, May 1, priced at CA $298 found 1 day ago

Alternative airports near Westchester

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city centre is 17 minutes. Flights from CA $471
MDW
Midway Intl.
CheapestClosest
Average driving time to city centre17 min
Flights from CA $471

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

July is typically the cheapest month to fly

From CA $109 - CA $427 per traveller.

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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.ca gives you the best tools to secure great deals on flights to Westchester. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Westchester. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Westchester.

Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Westchester flights with full confidence knowing that you've found the best deal online.

Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Westchester.

Looking to save even more? Get additional savings by bundling your Westchester flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Westchester trip!

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $267

Trending flights to Westchester

Prices were available within the past 7 days and start at CA $159 for one-way flights and CA $280 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Mon, May 11 - Mon, May 11
YUL
Montreal
MDW
Chicago
CA $280 Roundtrip, found 21 hours ago
CA $280
Roundtrip
found 21 hours ago
Select Porter Airlines flight, departing Mon, May 11 from Montreal to Chicago, returning Mon, May 11, priced at CA $280 found 21 hours ago
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