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Westchester County

$278+ 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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HPN
Jun 18 — Jun 251
Thu 6/18
Thu 6/25
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 May 19, 2026.

This American Airlines deal was found by Cheapflights users on 5/16. 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 6/15:17 pm
PWM
-
HPN
1 stop6h 09m
American Airlines
Sat 6/66:30 am
HPN
-
PWM
1 stop5h 15m
American Airlines
Deal found 5/16$413
This American Airlines deal was found by Cheapflights users on 5/17. 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 5/295:17 pm
PWM
-
HPN
1 stop6h 09m
American Airlines
Sun 5/315:29 pm
HPN
-
PWM
1 stop6h 30m
American Airlines
Deal found 5/17$568
This Expedia deal was found by Cheapflights users on 5/17. 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.
Sun 6/146:00 am
PWM
-
HPN
2 stops8h 35m
JetBlue
Sun 6/218:29 pm
HPN
-
PWM
2 stops17h 06m
JetBlue
Deal found 5/17$573
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Mon 6/156:13 pm
PWM
-
HPN
1 stop17h 14m
Breeze Airways
Sun 6/218:00 am
HPN
-
PWM
2 stops25h 12m
Breeze Airways
Deal found 5/18$643
This American Airlines deal was found by Cheapflights users on 5/17. 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.
Sun 6/145:42 am
PWM
-
HPN
1 stop4h 48m
American Airlines
Sun 6/215:29 pm
HPN
-
PWM
1 stop6h 30m
American Airlines
Deal found 5/17$651
This Expedia deal was found by Cheapflights users on 5/16. 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 6/16:00 am
PWM
-
HPN
2 stops16h 46m
JetBlue
Sat 6/68:35 am
HPN
-
PWM
2 stops15h 23m
JetBlue
Deal found 5/16$688
This American Airlines deal was found by Cheapflights users on 5/18. 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 6/151:36 pm
PWM
-
HPN
2 stops20h 54m
American Airlines
Sun 6/215:29 pm
HPN
-
PWM
2 stops19h 10m
American Airlines
Deal found 5/18$815
This FlightHub deal was found by Cheapflights users on 5/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
PWM
-
HPN
2 stops16h 33m
JetBlue
Sun 5/318:35 am
HPN
-
PWM
2 stops29h 00m
JetBlue
Deal found 5/17$852
This Gotogate deal was found by Cheapflights users on 5/17. 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.
Sun 6/147:56 pm
PWM
-
HPN
3 stops39h 31m
Breeze Airways
Sun 6/2112:07 pm
HPN
-
PWM
2 stops21h 05m
Breeze Airways
Deal found 5/17$1,000

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 May 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$413
(American Airlines)

One-way from

$278
(FlightHub)

Popular in

March

Cheapest in

October

Average price

$179
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. 11% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 19, 2026.
Use the filters below to find and compare flights from Portland to Westchester County that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Mon 6/1

5:17 pm-11:26 pm

1 stop6h 09m

White Plains Westchester County

Sat 6/6

6:30 am-11:45 am

1 stop5h 15m

$413

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Mon 6/15

11:58 am-6:29 pm

1 stop6h 31m

White Plains Westchester County

Sun 6/21

5:29 pm-11:59 pm

1 stop6h 30m

$651
Quickest round-trip

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Sun 6/14

5:42 am-10:30 am

1 stop4h 48m

White Plains Westchester County

Sun 6/21

5:29 pm-11:59 pm

1 stop6h 30m

$651

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Mon 6/1

6:00 am-10:46 pm

2 stops16h 46m

White Plains Westchester County

Sat 6/6

8:35 am-11:58 pm

2 stops15h 23m

$688

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Fri 5/29

3:05 pm-10:30 am

2 stops19h 25m

White Plains Westchester County

Sun 5/31

11:00 am-11:59 pm

1 stop12h 59m

$770

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Sun 6/14

7:56 pm-11:27 am

3 stops39h 31m

White Plains Westchester County

Sun 6/21

12:07 pm-9:12 am

2 stops21h 05m

$1,000

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Mon 6/15

6:13 pm-9:00 pm

3 stops26h 47m

White Plains Westchester County

Sun 6/21

12:07 pm-9:12 am

2 stops21h 05m

$1,154
Cheapest one-way

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Fri 6/19

2:30 pm-2:35 pm

2 stops24h 05m

$278

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Fri 6/19

6:13 pm-9:00 pm

1 stop26h 47m

$305

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Fri 6/5

6:13 pm-9:00 pm

1 stop26h 47m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/15

Showing 1-10 of 17 resultsSorted by cheapest first
1
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 6h 09m. American Airlines provides one of the quickest options available for as low as $413. 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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