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Westchester County

$165+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HPN
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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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 November 4, 2025.

This American Airlines deal was found by Cheapflights users on 11/4. 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 11/195:43 amPWM - HPN
1 stop5h 14mAmerican Airlines
Sun 11/236:30 amHPN - PWM
1 stop5h 16mAmerican Airlines
Deal found 11/4$352
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Fri 11/75:43 amPWM - HPN
1 stop5h 14mAmerican Airlines
Sun 11/96:30 amHPN - PWM
1 stop5h 16mAmerican Airlines
Deal found 11/3$417
This American Airlines deal was found by Cheapflights users on 11/4. 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 11/4$447
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Wed 11/196:18 pmPWM - HPN
2 stops18h 21mBreeze Airways
Sun 11/2312:09 pmHPN - PWM
1 stop29h 16mBreeze Airways
Deal found 11/4$508
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:05 pmPWM - HPN
1 stop18h 49mBreeze Airways
Sun 11/912:09 pmHPN - PWM
2 stops20h 57mBreeze Airways
Deal found 11/3$568
This JetBlue deal was found by Cheapflights users on 11/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/204:17 pmPWM - HPN
1 stop7h 12mJetBlue
Mon 12/228:40 amHPN - PWM
1 stop6h 45mJetBlue
Deal found 11/2$706
This FlightHub deal was found by Cheapflights users on 11/4. 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 11/216:05 pmPWM - HPN
1 stop18h 49mBreeze Airways
Sun 11/2312:09 pmHPN - PWM
2 stops20h 57mBreeze Airways
Deal found 11/4$732

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 November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$292
(American Airlines)

One-way from

$165
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$240
Provider with most accurate pricing for Portland-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Portland-New York (NYC) flights.
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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 November 2025
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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 November 4, 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

Wed 11/19

5:43 am-10:57 am

1 stop5h 14m

White Plains Westchester County

Sun 11/23

6:30 am-11:46 am

1 stop5h 16m

$352

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

$447

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Wed 11/19

6:18 pm-12:39 pm

2 stops18h 21m

White Plains Westchester County

Sun 11/23

12:09 pm-5:25 pm

1 stop29h 16m

$508

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Sat 12/20

4:17 pm-11:29 pm

1 stop7h 12m

White Plains Westchester County

Mon 12/22

8:40 am-3:25 pm

1 stop6h 45m

$706

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Fri 11/21

6:05 pm-12:54 pm

1 stop18h 49m

White Plains Westchester County

Sun 11/23

12:09 pm-9:06 am

2 stops20h 57m

$732

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Wed 4/1

12:26 pm-6:17 pm

1 stop5h 51m

White Plains Westchester County

Thu 4/2

11:27 am-4:45 pm

1 stop5h 18m

$772

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Wed 4/1

6:00 am-9:36 pm

2 stops15h 36m

White Plains Westchester County

Thu 4/2

6:00 am-11:05 pm

2 stops17h 05m

$950

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Mon 11/17

9:46 am-11:29 am

2 stops25h 43m

$165

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Fri 11/14

6:05 pm-12:54 pm

1 stop18h 49m

$171

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Wed 11/12

6:18 pm-12:39 pm

2 stops18h 21m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 14 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 5h 14m. American Airlines provides one of the quickest options available for as low as $352. 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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