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Westchester County

$130+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HPN
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap 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 September 16, 2025.

Round-trip from

$257
(American Airlines)

One-way from

$130
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$167
From Portland to Westchester County
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One-way flight from Portland to Westchester County
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Highest demand for flights based on searches. 14% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 10/305:21 pmPWM - HPN
1 stop6h 08mAmerican Airlines
Sat 11/13:00 pmHPN - PWM
1 stop6h 21mAmerican Airlines
Deal found 9/14$257
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 10/305:21 pmPWM - HPN
1 stop6h 08mAmerican Airlines
Sun 11/25:30 amHPN - PWM
1 stop5h 16mAmerican Airlines
Deal found 9/14$287
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/302:02 pmPWM - HPN
1 stop4h 18mAmerican Airlines
Sat 10/46:30 amHPN - PWM
1 stop5h 14mAmerican Airlines
Deal found 9/14$422
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/215:43 amPWM - HPN
1 stop5h 14mAmerican Airlines
Sun 11/235:21 pmHPN - PWM
1 stop6h 20mAmerican Airlines
Deal found 9/14$444
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/2612:27 pmPWM - HPN
1 stop5h 53mAmerican Airlines
Sun 9/286:30 amHPN - PWM
1 stop5h 14mAmerican Airlines
Deal found 9/15$474
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:09 amPWM - HPN
2 stops15h 39mJetBlue
Sun 9/287:30 amHPN - PWM
2 stops14h 37mJetBlue
Deal found 9/15$565
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:05 pmPWM - HPN
1 stop18h 49mMultiple Airlines
Sun 9/281:19 pmHPN - PWM
2 stops19h 47mMultiple Airlines
Deal found 9/15$707

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 September 16, 2025.
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

Thu 10/30

5:21 pm-11:29 pm

1 stop6h 08m

White Plains Westchester County

Sat 11/1

3:00 pm-9:21 pm

1 stop6h 21m

$257

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Thu 10/30

5:21 pm-11:29 pm

1 stop6h 08m

White Plains Westchester County

Sun 11/2

5:30 am-10:46 am

1 stop5h 16m

$287

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Tue 9/30

2:02 pm-6:20 pm

1 stop4h 18m

White Plains Westchester County

Sat 10/4

6:30 am-11:44 am

1 stop5h 14m

$422

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Fri 11/21

5:43 am-10:57 am

1 stop5h 14m

White Plains Westchester County

Sun 11/23

5:21 pm-11:41 pm

1 stop6h 20m

$444

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Fri 9/26

12:27 pm-6:20 pm

1 stop5h 53m

White Plains Westchester County

Sun 9/28

6:30 am-11:44 am

1 stop5h 14m

$474

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Fri 9/26

7:09 am-10:48 pm

2 stops15h 39m

White Plains Westchester County

Sun 9/28

7:30 am-10:07 pm

2 stops14h 37m

$565

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Mon 12/8

6:05 pm-11:29 am

1 stop17h 24m

$130

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Fri 10/3

6:05 pm-12:54 pm

1 stop18h 49m

$249

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Sun 10/5

5:45 am-10:36 am

1 stop4h 51m

$379

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Sat 11/22

3:56 pm-10:54 pm

1 stop6h 58m

$528

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 12 results
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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 6h 08m. American Airlines provides one of the quickest options available for as low as $257. There are 249 mi between Portland, Maine and Westchester County.

  • What are the cheapest flights from Portland, Maine to Westchester County?

    The cheapest flight price from Portland, Maine to Westchester County is $169. On average you can expect to pay $222. The most popular route, (Portland - White Plains Westchester County), can usually be booked for $257.

  • 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.

  • What is the cheapest month to book a flight from Portland, Maine to Westchester County?

    Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Westchester County (average of $276). Flying from Portland, Maine to Westchester County in March is currently the most expensive (average of $338). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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