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Westchester County

$176+ Cheap flights from Portland, ME (PWM) to Westchester County

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HPN
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap flight deals from Portland to Westchester County

Cheapest flights from Portland to Westchester County
Explore the most affordable flight options available from Portland to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.

This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:55 am
PWM
-
HPN
1 stop7h 24m
American Airlines
Tue 3/106:00 am
HPN
-
PWM
1 stop4h 28m
American Airlines
Deal found 2/3$367
This American Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/612:46 pm
PWM
-
HPN
1 stop5h 22m
American Airlines
Sun 2/85:15 pm
HPN
-
PWM
1 stop6h 28m
American Airlines
Deal found 2/1$407
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/186:00 am
PWM
-
HPN
1 stop4h 58m
American Airlines
Sun 2/226:30 am
HPN
-
PWM
1 stop3h 53m
American Airlines
Deal found 2/3$630
This Gotogate deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1810:57 am
PWM
-
HPN
2 stops24h 31m
Breeze Airways
Sun 2/228:00 am
HPN
-
PWM
3 stops26h 49m
Breeze Airways
Deal found 2/3$977
This Gotogate deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/69:47 am
PWM
-
HPN
3 stops34h 43m
Breeze Airways
Sun 2/812:08 pm
HPN
-
PWM
1 stop28h 18m
Breeze Airways
Deal found 2/1$985

Find flight deals from Portland to Westchester County

Keep the following information in mind while searching for Portland to Westchester County flight deals. Data was last updated February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$367
(American Airlines)

One-way from

$176
(Kiwi.com)

Popular in

March

Cheapest in

May

Average price

$243
Provider with most accurate pricing for Portland-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-New York (NYC) flights.
Search Deals
From Portland to Westchester County
Search Deals
One-way flight from Portland to Westchester County
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Westchester County that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 4, 2026.
Use the filters below to find and compare flights from Portland to Westchester County that are best for you.

Fly from

Portland

Fly to

Westchester County

Route

Depart

Return

Price

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Tue 3/3

10:55 am-6:19 pm

1 stop7h 24m

White Plains Westchester County

Tue 3/10

6:00 am-10:28 am

1 stop4h 28m

$367

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Wed 2/18

6:00 am-10:58 am

1 stop4h 58m

White Plains Westchester County

Sun 2/22

6:30 am-10:23 am

1 stop3h 53m

$630

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Wed 2/18

10:57 am-11:28 am

2 stops24h 31m

White Plains Westchester County

Sun 2/22

8:00 am-10:49 am

3 stops26h 49m

$977

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Mon 2/9

5:06 pm-11:28 am

1 stop18h 22m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Best time to book a flight from Portland to Westchester County

Have a flexible travel schedule? Discover the best time to fly to Westchester County from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Portland to Westchester County
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Portland to Westchester County. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Portland to Westchester County?

    Portland (PWM), located 2.9 mi from the city center, is the airport you fly out of when you book flights from Portland to Westchester County.

  • How long is the flight from Portland, Maine to Westchester County?

    A quick flight from Portland, Maine to Westchester County can take about 7h 24m. American Airlines provides one of the quickest options available for as low as $367. There are 249 mi between Portland, Maine and Westchester County. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Portland to Westchester County that include hotel bookings?

    Yes. In addition to deals on Portland to Westchester County flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Westchester County?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Westchester County.

  • Can I find deals for business class flights from Portland to Westchester County?

    Yes. Cheapflights offers flight deals from Portland to Westchester County by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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