Cheap Flights from White Plains (HPN) to Pittsfield (PSF)

Popular airlines from Westchester County Airport (HPN) to Pittsfield, MA (PSF-Pittsfield Municipal)

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Frequently asked questions

How much does a flight from Westchester County Airport (HPN) to Pittsfield, MA (PSF-Pittsfield Municipal) cost?
Get a cheap one-way flight or cheap return flight from Westchester County Airport (HPN) to Pittsfield, MA (PSF-Pittsfield Municipal) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Westchester County Airport (HPN) to Pittsfield, MA (PSF-Pittsfield Municipal)?
Planning your getaway for may help you find better deals, as it's the cheapest month for flights between HPN and PSF. You'll typically find the lowest fares during the off-season.
What is the cheapest airline that flies from Westchester County Airport (HPN) to Pittsfield, MA (PSF-Pittsfield Municipal)?
To find the cheapest airline flying from HPN to PSF, use Expedia's filter tool. Tailor your search based on your travel style, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Westchester County Airport (HPN) to Pittsfield, MA (PSF-Pittsfield Municipal)?
There aren't any daily direct flights departing from Westchester County Airport (HPN) to Pittsfield, MA (PSF-Pittsfield Municipal). But you can choose flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds in no time.
What day of the week has the most flights from HPN to PSF?
Typically you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can change depending on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Westchester County Airport (HPN) to Pittsfield, MA (PSF-Pittsfield Municipal)?
Choose a flight from Westchester County Airport (HPN) to Pittsfield, MA (PSF-Pittsfield Municipal) that leaves before 3 PM to reduce the likelihood of delays. Later departures have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Westchester County Airport (HPN) to Pittsfield, MA (PSF-Pittsfield Municipal) last-minute?
Holding off until just before your departure to book your flight from HPN to PSF often results in higher prices. While you may come across some last-minute deals, there's no guarantee. Be flexible with your itinerary to boost your chances of snagging a bargain.
Is it cheaper to book a HPN to PSF flight and hotel package?
Securing a HPN to PSF flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Select from our wide range of hotels and then add activities, car rentals and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Westchester County Airport (HPN) to Pittsfield, MA (PSF-Pittsfield Municipal)?
If you reserved your HPN to PSF flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

Travel information

Origin airport
Westchester County
Destination airport
Pittsfield Municipal
Distance
96 mi

Book with confidence

White Plains to Pittsfield Flights

The cheapest times to fly from White Plains to Pittsfield

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from White Plains to Pittsfield are during the month of . You can find some of the cheapest flights from White Plains to Pittsfield with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from White Plains to Pittsfield

Sunday is one of the best days to book for cheap flights from White Plains to Pittsfield: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from White Plains to Pittsfield

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from White Plains to Pittsfield in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap White Plains to Pittsfield flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your White Plains to Pittsfield airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

White Plains to Pittsfield Flights

Explore a world of travel with Expedia

*Available to One Key members.