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254 € Cheap Flights from Chicago O'Hare International to Westchester County

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      Travellers and cabin class, 1 Adult, Economy
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      Compare Chicago O'Hare International to Westchester County flight deals

      Find the cheapest month or even day of the year to fly to Westchester County

      Book the best Westchester County fare with no extra fees

      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 323 €. Find the lowest prices on one-way and return tickets right here.
      White Plains.254 € per passenger.Departing Wed, 28 Oct, returning Mon, 2 Nov.Return flight with Frontier Airlines and Breeze Airways.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 28 Oct, arriving in Westchester County.Inbound indirect flight with Breeze Airways, departs from Westchester County on Mon, 2 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From 254 €, select.
      White Plains.292 € per passenger.Departing Thu, 5 Nov, returning Tue, 10 Nov.Return flight with Frontier Airlines and Breeze Airways.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 5 Nov, arriving in Westchester County.Inbound indirect flight with Breeze Airways, departs from Westchester County on Tue, 10 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From 292 €, select.
      White Plains.313 € per passenger.Departing Wed, 16 Dec, returning Wed, 20 Jan.Return flight with Frontier Airlines and Breeze Airways.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 16 Dec, arriving in Westchester County.Inbound indirect flight with Breeze Airways, departs from Westchester County on Wed, 20 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From 313 €, select.
      White Plains.320 € per passenger.Departing Thu, 3 Dec, returning Mon, 7 Dec.Return flight with Frontier Airlines and Breeze Airways.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 3 Dec, arriving in Westchester County.Inbound indirect flight with Breeze Airways, departs from Westchester County on Mon, 7 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From 320 €, select.
      White Plains.323 € per passenger.Departing Fri, 23 Oct, returning Tue, 27 Oct.Return flight with Frontier Airlines and Breeze Airways.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri, 23 Oct, arriving in Westchester County.Inbound indirect flight with Breeze Airways, departs from Westchester County on Tue, 27 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 323 €, select.
      White Plains.338 € per passenger.Departing Tue, 26 Jan, returning Mon, 1 Feb.Return flight with Frontier Airlines and Breeze Airways.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 26 Jan, arriving in Westchester County.Inbound indirect flight with Breeze Airways, departs from Westchester County on Mon, 1 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From 338 €, select.
      White Plains.362 € per passenger.Departing Tue, 15 Jun, returning Tue, 22 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 15 Jun, arriving in Westchester County.Inbound indirect flight with Delta, departs from Westchester County on Tue, 22 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From 362 €, select.
      White Plains.366 € per passenger.Departing Wed, 17 Mar, returning Wed, 24 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Wed, 17 Mar, arriving in Westchester County.Inbound indirect flight with Delta, departs from Westchester County on Wed, 24 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From 366 €, select.
      White Plains.381 € per passenger.Departing Sat, 24 Oct, returning Sun, 25 Oct.Return flight with American Airlines.Outbound direct flight with American Airlines departs from Chicago O'Hare International on Sat, 24 Oct, arriving in Westchester County.Inbound direct flight with American Airlines departs from Westchester County on Sun, 25 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 381 €, select.
      White Plains.437 € per passenger.Departing Mon, 19 Oct, returning Sat, 2 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 19 Oct, arriving in Westchester County.Inbound indirect flight with Delta, departs from Westchester County on Sat, 2 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From 437 €, select.
      White Plains.445 € per passenger.Departing Mon, 30 Nov, returning Thu, 3 Dec.Return flight with Frontier Airlines and Breeze Airways.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 30 Nov, arriving in Westchester County.Inbound indirect flight with Breeze Airways, departs from Westchester County on Thu, 3 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From 445 €, select.
      White Plains.474 € per passenger.Departing Fri, 25 Sep, returning Sun, 27 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Fri, 25 Sep, arriving in Westchester County.Inbound indirect flight with Delta, departs from Westchester County on Sun, 27 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 474 €, select.
      White Plains.474 € per passenger.Departing Sun, 27 Sep, returning Sun, 4 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Sun, 27 Sep, arriving in Westchester County.Inbound indirect flight with Delta, departs from Westchester County on Sun, 4 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 474 €, select.
      How did we find these deals? The deals you see here are the lowest prices for flight tickets from Chicago O'Hare International to Westchester County found in the last 4 days, and are subject to change and availability.

      Find the cheapest month to fly from Chicago O'Hare International to Westchester County

      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 November.
      Sep
      from 474 €
      Oct
      from 323 €
      Nov
      from 292 €
      Dec
      from 320 €
      Jan
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      Feb
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      Mar
      from 366 €
      Apr
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      May
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      Jun
      from 362 €
      Jul
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      Aug
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      Direct flights from Chicago O'Hare International to Westchester County

      Alaska Airlines
      American Airlines
      Envoy Air
      PSA Airlines
      Qatar Airways

      Chicago to White Plains: Flight information

      The things to know before you go.
      Cheapest flight found254 €
      Cheapest month to flyOctober
      Average flight time2 hrs, 22 mins
      Most popular airlineAmerican Airlines
      Average flights per week113

      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 254 €. 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 22 minutes is the average flight time from Chicago O'Hare International to Westchester County.
      American Airlines, Envoy Air and Alaska Airlines fly direct from Chicago O'Hare International to Westchester County.
      As of September 2026, there are 113 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 October.
      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, 28 October 2026.
      Yes – the average flight time is 2 hours and 22 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 and American Airlines offer the cheapest flight tickets to Westchester County.

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

      • The average duration of a direct flight from Chicago O'Hare International Airport to Westchester County Airport is 2 hours 15 minutes.

      • White Plains is one hour ahead of Chicago and is in the UTC-5 timezone.

      • You can choose from 29 weekly Chicago O'Hare International Airport to Westchester County Airport flights. The 08:00 departure with American Airlines is the earliest available. American Airlines operates the last service of the day at 20:10.

      • For a smooth journey, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This way, you'll have plenty of time to catch your ORD to HPN flight.

      • During popular months such as July, it's a good idea to get to the airport earlier than normal. Plan to arrive two hours before a domestic departure and four hours ahead for international flights when you travel during peak periods in general.

      • Getting to White Plains (and then exploring more of the United States!) is a breeze with American Airlines. This popular carrier has direct flights from Chicago O'Hare International Airport to Westchester County Airport.

      • Most passengers choose to fly with American Airlines on this route.

      • With 71.39% of services arriving as scheduled, American Airlines is the most punctual carrier offering ORD to HPN flights.

      • We make it a breeze to book a flight with a stopover. To see your options for tickets from Chicago O'Hare International Airport to Westchester County Airport, deselect 'Direct flights only.' Then, choose a flight that has a stop long enough to visit the city of your choice. Top stopovers between ORD and HPN include:

        • Charlotte Douglas Airport

        • Detroit Wayne County Airport

        • Washington Ronald Reagan Airport

      Handy information about Chicago O'Hare International Airport (ORD)

      • ORD's address is 10000 West O'Hare.

      • 70% of flights that take off from Chicago O'Hare International Airport land at their destination on time.

      • Chicago O'Hare International Airport is about 27 kilometres from central Chicago. If you're driving, catching a taxi or ride-sharing from the centre, it'll take 30 minutes or so to arrive, depending on the traffic.

      • The journey when using public transport takes roughly 45 minutes.

      • Taking an early flight from Chicago O'Hare International Airport to Westchester County Airport? Avoid the stress of rushing to the airport (and enjoy a little extra shut-eye) by choosing one of these hotels near ORD:

      Arriving at Westchester County Airport (HPN)

      • Consider a stay at Sonesta White Plains Downtown after arriving from your Chicago O'Hare International Airport to Westchester County Airport flight. It's a short drive from HPN and a comfy option if you're eager to relax as soon as possible.

      • Grab a Westchester County Airport rental car and explore White Plains and beyond with your own wheels. Dollar, Thrifty and Hertz are top outlets you can book with here.

      • Booking your vehicle from Westchester County Airport around one week ahead can help you secure the lowest rate.

      Getting from Westchester County Airport (HPN) to central White Plains

      • HPN is located at 240 Airport Road, Suite 202.

      • Westchester County Airport is roughly 6 kilometres from central White Plains. Driving there takes about 10 minutes.

      • Getting there by public transport takes roughly 25 minutes.

      When to fly to Westchester County Airport (HPN)

      • The quietest month for a flight from Chicago O'Hare International Airport to Westchester County Airport is March, while July is the busiest. Pick the ideal time to go to White Plains based on whether you prefer a faster pace or a more relaxed vibe.

      • Before locking in your flight from Chicago O'Hare International Airport to Westchester County Airport, think about the type of weather you like. July is the warmest month in White Plains, with the temperature ranging from 17ºC (63ºF) to 31ºC (88ºF).

      • If you'd rather travel in cooler conditions, search for a cheap ticket from ORD to HPN in January. Temperatures average between -7ºC (19ºF) and 7ºC (45ºF) then.

      Explore more of the United States

      • You've seen White Plains, now it's time to discover other corners of the United States. Travel around 56 kilometres south-west to New York to check off its leading sights. From Central Park to Statue of Liberty and Metropolitan Museum of Art, you'll have a full itinerary ahead.

      • If there's time to check out another major destination in the United States, head for Philadelphia, about 177 kilometres south-west of White Plains. Independence Hall, Liberty Bell and Philadelphia Museum of Art are key reasons to visit.

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.