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C$244 Cheap Flights from Chicago O'Hare International (ORD) to Westchester County (HPN)

Compare Chicago O'Hare International to Westchester County flight deals

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Flight deals from Chicago O'Hare International to Westchester County

Looking for a cheap last-minute deal or the best return flight from Chicago O'Hare International Airport to Westchester County Airport? If you want to travel next month, return fares start from C$570. Find the lowest prices on one-way and return tickets right here.
White Plains.C$244 per passenger.Departing Tue., Sep. 8.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue., Sep. 8, arriving in Westchester County.Price includes taxes and charges.From C$244, select.
White Plains.C$254 per passenger.Departing Wed., Jul. 1.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed., Jul. 1, arriving in Westchester County.Price includes taxes and charges.From C$254, select.
White Plains.C$268 per passenger.Departing Fri., Aug. 14.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri., Aug. 14, arriving in Westchester County.Price includes taxes and charges.From C$268, select.
White Plains.C$288 per passenger.Departing Fri., Jun. 5.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri., Jun. 5, arriving in Westchester County.Price includes taxes and charges.From C$288, select.
White Plains.C$310 per passenger.Departing Thu., Oct. 15.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu., Oct. 15, arriving in Westchester County.Price includes taxes and charges.From C$310, select.
White Plains.C$460 per passenger.Departing Thu., May 28.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu., May 28, arriving in Westchester County.Price includes taxes and charges.From C$460, select.

Find the cheapest month to fly from Chicago O'Hare International to Westchester County from C$244 one-way

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago O'Hare International to Westchester County flights are currently cheapest in September.
May
from C$459
Jun.
from C$288
Jul.
from C$254
Aug.
from C$268
Sep.
from C$244
Oct.
from C$310
Nov.
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Dec.
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Jan.
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Feb.
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Mar.
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Apr.
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Which airlines fly from Chicago O'Hare International to Westchester County?

Chicago to White Plains: Flight information

The things to know before you go.
Cheapest flight foundC$244
Cheapest month to flySeptember
Average flight time2 hrs, 20 mins
Most popular airlineEnvoy Air
Average flights per week100

Finding cheap flights from Chicago O'Hare International to Westchester County: Frequently asked questions

The best price we found for a return flight from Chicago O'Hare International to Westchester County is C$498. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 20 minutes is the average flight time from Chicago O'Hare International to Westchester County.
Envoy Air, American Airlines and Alaska Airlines fly direct from Chicago O'Hare International to Westchester County.
As of May 2026, there are 100 flights per week flying from Chicago O'Hare International to Westchester County.
The cheapest month to fly from Chicago O'Hare International to Westchester County is usually July.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago O'Hare International Airport to Westchester County Airport on Wednesday, July 29, 2026.
Yes – the average flight time is 2 hours and 20 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Westchester County but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to White Plains is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Frontier Airlines offers the cheapest flight tickets to Westchester County.

Flying from O'Hare International Airport (ORD) to Westchester County Airport (HPN): what you need to know

  • Around 2 hours 14 minutes is how long you can expect to be traveling on a direct flight from O'Hare International Airport to Westchester County Airport.

  • Take your pick of 29 weekly flights from O'Hare International Airport to Westchester County Airport. The 07:20 departure with American Airlines is the earliest you can take between ORD and HPN. American Airlines operates the latest service of the day at 18:39 if you're not into early starts.

  • If you're jetting off during a public holiday or other peak period, allow extra time. A good general rule is two hours ahead of domestic flights and up to four hours before international departures. Check-in and security lines will be longer.

  • If you want to break up your flight from O'Hare International Airport to Westchester County Airport, consider adding a stopover. Just deselect 'Direct flights only' and find a destination that catches your eye. Popular stopovers on the ORD - HPN route include:

    • Ronald Reagan National Airport

    • Detroit Metropolitan Wayne County Airport

    • Charlotte Douglas International Airport

How to find the cheapest flights from O'Hare International Airport (ORD) to Westchester County Airport (HPN)

  • C$244 is the best price for a one-way ticket from O'Hare International Airport to Westchester County Airport. A return flight starts at C$498. These prices can change based on demand and availability.

  • Book 9 months before you travel. After crunching the numbers on our calendar, this is how far you'll want to book ahead to secure cheap flight tickets from ORD to HPN.

  • Plan your trip for May. That's the cheapest month for flight tickets from O'Hare International Airport to Westchester County Airport. If you're flexible with your dates, try out the 'Whole month' tool to see the lowest airfare across every month.

  • Set up a Price Alert for cheap flight tickets from ORD to HPN. There's no need to check every day to see whether prices have dropped. We'll notify you the moment the price changes.

  • Use filters to tailor your flights from O'Hare International Airport to Westchester County Airport. Simply select your ideal departure and arrival times, number of stops and airlines. Or sort your results by 'Cheapest' to get the best deals.

Handy information about O'Hare International Airport (ORD)

Plan the rest of your trip from Chicago to White Plains

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.