Cheap Flights to Westchester , IL from CA $152

View CA $152 flight on Sat, Oct. 25, 2025Opens in a new window

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How much is the cheapest flight to Westchester?

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $244 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, Nov. 6 - Sun, Nov. 9
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, found 13 hours ago
CA $244
Roundtrip
found 13 hours ago
Select Air Canada flight, departing Thu, Nov. 6 from Toronto to Chicago, returning Sun, Nov. 9, priced at CA $244 found 13 hours ago
United
Sat, Nov. 1 - Mon, Nov. 3
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, just found
CA $244
Roundtrip
just found
Select United flight, departing Sat, Nov. 1 from Toronto to Chicago, returning Mon, Nov. 3, priced at CA $244 just found
Porter Airlines
Tue, Jul. 22 - Mon, Aug. 11
YTZ
Toronto
MDW
Chicago
CA $256 Roundtrip, found 1 day ago
CA $256
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Tue, Jul. 22 from Toronto to Chicago, returning Mon, Aug. 11, priced at CA $256 found 1 day ago
American Airlines
Sat, Nov. 1 - Thu, Nov. 6
YYZ
Toronto
ORD
Chicago
CA $261 Roundtrip, found 21 hours ago
CA $261
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Sat, Nov. 1 from Toronto to Chicago, returning Thu, Nov. 6, priced at CA $261 found 21 hours ago
Air Transat
Wed, Jul. 30 - Mon, Sep. 8
YTZ
Toronto
MDW
Chicago
CA $292 Roundtrip, found 6 days ago
CA $292
Roundtrip
found 6 days ago
Select Air Transat flight, departing Wed, Jul. 30 from Toronto to Chicago, returning Mon, Sep. 8, priced at CA $292 found 6 days ago

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

June is typically the cheapest month to fly

From CA $105 - CA $339 per traveller.

Graph displaying average flight prices per month

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!

Frequently asked questions

What is the name of Westchester's airport?
Westchester is served by multiple airports, but most visitors touch down at O'Hare Intl. Airport (ORD).
How far is O'Hare Intl. Airport (ORD) from central Westchester?
ORD is 14 kilometres from central Westchester, so be prepared for a reasonable commute into the centre.
What airport is best to fly into Westchester?
A flight to Westchester means hopping off the plane at O'Hare Airport or MDW. The first is 14 kilometres away from the centre of the city. The second one is 13 kilometres away.
How many airlines fly to Westchester?
Westchester is serviced by 51 airlines from at least 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 come from New York, with United Airlines having the most services on this route.
How many nonstop flights are there to Westchester?
With roughly 7,564 nonstop flights every week, you'll be hitting the tarmac in Westchester before you can ask, "Are we there yet?"
Where are the most popular flights to Westchester departing from?
Travellers often depart from New York, Washington and Dallas airports when heading to Westchester.
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?
We all know those fortunate travellers who somehow grab super cheap airfares whenever they fly. Eager to know how to do it for your Westchester vacation? Don't leave it until the very last minute to secure your flight. Don't stop there, though. Do some research and see if there is more than one airport at your destination. Prices often differ depending on the airport you jet into. Don't forget to compare fares across airlines as well. And finally, remember that the early bird catches the worm. Know what a typical airfare costs and have your credit card ready to secure your ticket as soon as you spot a bargain. The sweetest deals don't last long.
Do you have any tips for my flight to Westchester?
If you're not prepared, air travel can be testing. But don't hit the panic button just yet. Follow these useful tips for a comfortable start to your getaway in Westchester. What to pack in your hand luggage:

  • It's easy --- first, put in your passport, official ID, cash and medications. Next, you'll need some in-flight entertainment to help pass the time. A juicy novel and a phone crammed with your favourite movies are some fantastic options. If you intend to take a short nap, a comfy neck pillow and some earplugs will also come in handy. Finally, make room for a few toiletry items to ensure you arrive looking fresh and raring to go.

Do not pack the following items in your hand luggage:

  • Make sure you don't have sharp objects (like a pocket knife) lurking in your carry-on luggage. Other banned items include explosive or flammable goods, like aerosols and matches, and liquids and gels in containers larger than 3.4 ounces (100 millilitres).

What to wear on a flight:

  • You'll want to choose comfort over style. Prepare for temperature changes in the cabin by dressing in layers, and wear flat, slightly roomy shoes like slip-ons.
  • Caused by sustained periods of inactivity, deep vein thrombosis (DVT) is a blood clot condition that can affect some passengers during long-haul flights. Reduce the risks by drinking water, keeping your legs and feet moving and wearing compression socks to help your circulation.

How to get through airport security fast when flying to Westchester?
It's all about being prepared. We've compiled some useful tips for a speedy trip through security. Watch out Westchester, here you come:

  • Security personnel first need to determine that you have a valid ID and travel documents before anything else. Have them in your hand, ready for inspection.
  • Time to strip down. Well sort of. Your jacket, belt, keys and other small items, like coins, will need to go through the X-ray machine. Make your life easier by removing them before your turn.
  • For just a few minutes, you'll have to unplug from the digital world. Your phone, laptop and any other electronic devices must also be sent through the scanner.
  • Want to bring along your favourite cologne? As long as the volume is no larger than 3.4 ounces (100 millilitres) and it's stored in a zip-close bag, it's OK to bring with you in your carry-on luggage.
  • Slip-on shoes are a good footwear choice as you're less likely to be asked to remove them when passing through security. Safety boots and other heavy shoes are often subjected to additional screening.
  • Airlines won't allow any sharp items or pocket knives in the cabin. If you need to bring these kinds of items, pack them safely in your checked baggage.

Flights to Westchester information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $244

Trending flights to Westchester

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $244 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, Nov. 6 - Sun, Nov. 9
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, found 13 hours ago
CA $244
Roundtrip
found 13 hours ago
Select Air Canada flight, departing Thu, Nov. 6 from Toronto to Chicago, returning Sun, Nov. 9, priced at CA $244 found 13 hours ago
*Available to Expedia members.