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Westchester County

$214+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HPN
Aug 30 — Sep 61
Sat 8/30
Sat 9/6
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 August 25, 2025.

Round-trip from

$307
(American Airlines)

One-way from

$214
(Expedia)

Popular in

February

Cheapest in

September

Average price

$182
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. 17% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 25, 2025.

This American Airlines deal was found by Cheapflights users on 8/23. 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 8/23$307
This Expedia deal was found by Cheapflights users on 8/23. 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.
Mon 9/227:09 amPWM - HPN
2 stops15h 39mJetBlue
Mon 9/297:30 amHPN - PWM
2 stops14h 37mJetBlue
Deal found 8/23$348
This Expedia deal was found by Cheapflights users on 8/24. 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 10/32:17 pmPWM - HPN
2 stops19h 49mJetBlue
Mon 10/67:30 amHPN - PWM
2 stops15h 34mJetBlue
Deal found 8/24$363
This American Airlines deal was found by Cheapflights users on 8/23. 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.
Sat 8/306:00 amPWM - HPN
1 stop4h 30mAmerican Airlines
Mon 9/16:30 amHPN - PWM
1 stop5h 04mAmerican Airlines
Deal found 8/23$377
This Expedia deal was found by Cheapflights users on 8/24. 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.
Tue 9/97:09 amPWM - HPN
2 stops11h 55mJetBlue
Fri 9/198:55 pmHPN - PWM
2 stops16h 27mJetBlue
Deal found 8/24$400
This Expedia deal was found by Cheapflights users on 8/23. 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.
Thu 10/27:09 amPWM - HPN
2 stops15h 39mJetBlue
Sun 10/58:55 pmHPN - PWM
2 stops16h 27mJetBlue
Deal found 8/23$402
This American Airlines deal was found by Cheapflights users on 8/23. 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.
Mon 9/2212:27 pmPWM - HPN
1 stop5h 53mAmerican Airlines
Mon 9/295:29 pmHPN - PWM
1 stop6h 16mAmerican Airlines
Deal found 8/23$412
This American Airlines deal was found by Cheapflights users on 8/24. 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 10/35:20 pmPWM - HPN
1 stop16h 02mAmerican Airlines
Mon 10/66:30 amHPN - PWM
2 stops14h 17mAmerican Airlines
Deal found 8/24$551
This American Airlines deal was found by Cheapflights users on 8/23. 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 10/27:05 amPWM - HPN
2 stops16h 21mAmerican Airlines
Sun 10/56:30 amHPN - PWM
1 stop17h 15mAmerican Airlines
Deal found 8/23$555
This Delta deal was found by Cheapflights users on 8/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/211:45 amPWM - HPN
1 stop28h 50mDelta
Sun 10/53:25 pmHPN - PWM
1 stop19h 11mDelta
Deal found 8/24$567

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 August 25, 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

Fri 10/3

5:20 pm-11:26 pm

1 stop6h 06m

White Plains Westchester County

Mon 10/6

6:30 am-11:54 am

1 stop5h 24m

$307

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

$307

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Tue 9/9

5:20 pm-11:26 pm

1 stop6h 06m

White Plains Westchester County

Fri 9/19

5:29 pm-11:45 pm

1 stop6h 16m

$307

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Tue 10/21

6:00 am-10:34 am

1 stop4h 34m

White Plains Westchester County

Fri 10/31

11:29 am-4:44 pm

1 stop5h 15m

$307

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Mon 9/22

7:09 am-10:48 pm

2 stops15h 39m

White Plains Westchester County

Mon 9/29

7:30 am-10:07 pm

2 stops14h 37m

$348

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Fri 10/3

2:17 pm-10:06 am

2 stops19h 49m

White Plains Westchester County

Mon 10/6

7:30 am-11:04 pm

2 stops15h 34m

$363

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Sat 8/30

6:00 am-10:30 am

1 stop4h 30m

White Plains Westchester County

Mon 9/1

6:30 am-11:34 am

1 stop5h 04m

$377

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Tue 9/9

7:09 am-7:04 pm

2 stops11h 55m

White Plains Westchester County

Fri 9/19

8:55 pm-1:22 pm

2 stops16h 27m

$400

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Thu 10/2

7:09 am-10:48 pm

2 stops15h 39m

White Plains Westchester County

Sun 10/5

8:55 pm-1:22 pm

2 stops16h 27m

$402

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Thu 10/2

12:27 pm-6:20 pm

1 stop5h 53m

White Plains Westchester County

Sun 10/5

5:29 pm-11:45 pm

1 stop6h 16m

$412

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/24

Showing 1-10 of 20 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 06m. American Airlines provides one of the quickest options available for as low as $307. There are 249 mi between Portland, Maine and Westchester County.

  • What are the cheapest airlines to fly from Portland, Maine to Westchester County one-way?

    To fly one-way, consider booking your trip with JetBlue, which is currently one of the cheapest options available, starting at $214. American Airlines flights start at $285 while deals on Breeze Airways start at $314 one-way.

  • 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 $307.

  • 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 $339). 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.

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