$144 Cheap Flights from White Plains (HPN) to Portland (PWM)

View $144 flight on Wed, Oct 15, 2025Opens in a new window

Popular airlines from Westchester County Airport (HPN) to Portland Intl. Jetport Airport (PWM)

Cheap Flights from White Plains to Portland (HPN-PWM)

Prices were available within the past 7 days and start at $144 for one-way flights and $271 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Tue, Oct 7 - Wed, Oct 22
HPN
White Plains
PWM
Portland
$271 Roundtrip, found 5 days ago
$271
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Oct 7 from White Plains to Portland, returning Wed, Oct 22, priced at $271 found 5 days ago
JetBlue Airways
Sat, Oct 18 - Wed, Oct 22
HPN
White Plains
PWM
Portland
$286 Roundtrip, found 3 days ago
$286
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sat, Oct 18 from White Plains to Portland, returning Wed, Oct 22, priced at $286 found 3 days ago
American Airlines
Tue, Sep 30 - Tue, Oct 7
HPN
White Plains
PWM
Portland
$287 Roundtrip, found 3 hours ago
$287
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Sep 30 from White Plains to Portland, returning Tue, Oct 7, priced at $287 found 3 hours ago
JetBlue Airways
Tue, Oct 7 - Wed, Oct 22
HPN
White Plains
PWM
Portland
$300 Roundtrip, found 2 days ago
$300
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Oct 7 from White Plains to Portland, returning Wed, Oct 22, priced at $300 found 2 days ago
JetBlue Airways
Tue, Oct 7 - Fri, Oct 24
HPN
White Plains
PWM
Portland
$310 Roundtrip, found 5 days ago
$310
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Oct 7 from White Plains to Portland, returning Fri, Oct 24, priced at $310 found 5 days ago
JetBlue Airways
Sat, Oct 4 - Wed, Oct 22
HPN
White Plains
PWM
Portland
$310 Roundtrip, found 2 days ago
$310
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Oct 4 from White Plains to Portland, returning Wed, Oct 22, priced at $310 found 2 days ago
JetBlue Airways
Wed, Oct 15 - Tue, Oct 21
HPN
White Plains
PWM
Portland
$313 Roundtrip, found 3 days ago
$313
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Oct 15 from White Plains to Portland, returning Tue, Oct 21, priced at $313 found 3 days ago
JetBlue Airways
Wed, Oct 22 - Sat, Oct 25
HPN
White Plains
PWM
Portland
$315 Roundtrip, found 2 days ago
$315
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Oct 22 from White Plains to Portland, returning Sat, Oct 25, priced at $315 found 2 days ago
JetBlue Airways
Tue, Oct 7 - Thu, Oct 23
HPN
White Plains
PWM
Portland
$315 Roundtrip, found 2 days ago
$315
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Oct 7 from White Plains to Portland, returning Thu, Oct 23, priced at $315 found 2 days ago
Delta
Fri, Oct 31 - Tue, Nov 11
HPN
White Plains
PWM
Portland
$480 Roundtrip, found 5 days ago
$480
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Oct 31 from White Plains to Portland, returning Tue, Nov 11, priced at $480 found 5 days ago

Find the cheapest month to fly from White Plains (HPN) to Portland (PWM)

October is typically the cheapest month to fly

From $196 - $706 per traveler.

Frequently asked questions

How much does a flight from Westchester County Airport (HPN) to Portland Intl. Jetport Airport (PWM) cost?
Get a cheap one-way flight from $144 or cheap return flight from $271 from Westchester County Airport (HPN) to Portland Intl. Jetport Airport (PWM) 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 Portland Intl. Jetport Airport (PWM)?
Planning your getaway for October is a great way to save, as it's the cheapest month for flights between HPN and PWM. You'll usually find the lowest prices during the off-season.
Which airlines fly direct from Westchester County Airport (HPN) to Portland Intl. Jetport Airport (PWM)?
You can't take a direct flight from White Plains, NY (HPN-Westchester County) to Portland Intl. Jetport Airport (PWM). However, you can arrive in Portland without any layovers by departing from John F. Kennedy Intl. Airport (JFK).
What is the cheapest airline that flies from Westchester County Airport (HPN) to Portland Intl. Jetport Airport (PWM)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll take you from HPN to PWM. Then, sort your results by "Price (lowest to highest)" to snap up a good deal.
How many flights per day from Westchester County Airport (HPN) to Portland Intl. Jetport Airport (PWM)?
There are no daily direct flights departing from Westchester County Airport (HPN) to Portland Intl. Jetport Airport (PWM). But you can opt for flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from HPN to PWM?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from HPN to PWM?
Consider booking with Breeze Airways if you'd like to fly straight from Westchester County Airport (HPN) to Portland Intl. Jetport Airport (PWM) without any delays. This airline has the best track record for punctuality, with an on-time performance of 88%. Want to be updated if anything changes? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from Westchester County Airport (HPN) to Portland Intl. Jetport Airport (PWM)?
Book a flight from Westchester County Airport (HPN) to Portland Intl. Jetport Airport (PWM) that leaves before 3 PM to reduce the risk of cancellations. Departures after this hour 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 Portland Intl. Jetport Airport (PWM) last-minute?
Last-minute fares from HPN to PWM are usually more expensive. For the lowest rates, start looking for flights well in advance. That being said, if you're flexible with your travel dates, you may land a cheap fare just before your departure.
Is it cheaper to book a HPN to PWM flight and hotel package?
Compared with arranging hotels and flights separately, booking a HPN to PWM flight and hotel package with Expedia could result in significant savings. Better still, having everything in one place will take the stress out of travel planning. Simply pick your flights and select from our wide range of hotels, then tailor your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Westchester County Airport (HPN) to Portland Intl. Jetport Airport (PWM)?
Typically, you can reschedule or cancel your HPN to PWM flight. However, additional charges may apply, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's rules and fees on flight changes, or if you'd like further details, head to our Customer Service portal.

Travel information

Travel information

Origin airport
Westchester County
Destination airport
Portland Intl. Jetport
Airlines serving
American Airlines, Delta, JetBlue Airways
Roundtrip price
$270
Distance
248 mi

Book with confidence

Book with confidence

White Plains to Portland Flights

The cheapest times to fly from White Plains to Portland

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 Portland are during the month of October. You can find some of the cheapest flights from White Plains to Portland with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from White Plains to Portland: 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 Portland

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 Portland in 2025. You can also book with separate airlines for your outbound and return journeys, from $144 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 Portland 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 Portland 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 Portland Flights

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Explore a world of travel with Expedia

*Available to One Key members.