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Westchester County

$237+ 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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HPN
maj 3 — maj 101
sön 5/3
sön 5/10
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 april 3, 2026.

This American Airlines deal was found by Cheapflights users on 3/30. 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.
tis 4/146:00 am
PWM
-
HPN
1 stop4h 30m
American Airlines
lör 4/186:30 am
HPN
-
PWM
1 stop3h 54m
American Airlines
Deal found 3/30$514
This American Airlines deal was found by Cheapflights users on 4/1. 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.
tors 4/166:00 am
PWM
-
HPN
1 stop4h 30m
American Airlines
mån 4/205:16 pm
HPN
-
PWM
1 stop6h 38m
American Airlines
Deal found 4/1$570
This Delta deal was found by Cheapflights users on 3/31. 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.
fre 5/812:55 pm
PWM
-
HPN
1 stop22h 55m
Delta
lör 5/95:15 pm
HPN
-
PWM
1 stop22h 52m
Delta
Deal found 3/31$705
This Delta deal was found by Cheapflights users on 3/31. 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.
tors 5/76:00 am
PWM
-
HPN
1 stop27h 48m
Delta
lör 5/912:50 pm
HPN
-
PWM
1 stop10h 19m
Delta
Deal found 3/31$725
This Delta deal was found by Cheapflights users on 3/31. 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.
tors 5/72:05 pm
PWM
-
HPN
1 stop19h 43m
Delta
sön 5/106:00 am
HPN
-
PWM
1 stop17h 09m
Delta
Deal found 3/31$755
This American Airlines deal was found by Cheapflights users on 3/30. 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.
tis 4/76:01 am
PWM
-
HPN
1 stop4h 29m
American Airlines
tis 4/75:16 pm
HPN
-
PWM
1 stop6h 38m
American Airlines
Deal found 3/30$807
This KAYAK deal was found by Cheapflights users on 3/31. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fre 5/86:13 pm
PWM
-
HPN
1 stop26h 17m
Breeze Airways
sön 5/1012:07 pm
HPN
-
PWM
2 stops21h 05m
Breeze Airways
Deal found 3/31$814
This KAYAK deal was found by Cheapflights users on 3/31. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tors 5/73:11 pm
PWM
-
HPN
2 stops26h 18m
Breeze Airways
lör 5/98:00 am
HPN
-
PWM
2 stops30h 26m
Breeze Airways
Deal found 3/31$1,068

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 april 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$514
(American Airlines)

One-way from

$237
(Kiwi.com)

Popular in

March

Cheapest in

May

Average price

$197
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. 9% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 april 3, 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
Quickest round-trip

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

tis 4/14

6:00 am-10:30 am

1 stop4h 30m

White Plains Westchester County

lör 4/18

6:30 am-10:24 am

1 stop3h 54m

$514

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

tors 4/16

6:00 am-10:30 am

1 stop4h 30m

White Plains Westchester County

mån 4/20

5:16 pm-11:54 pm

1 stop6h 38m

$570

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

tors 5/7

6:00 am-9:48 am

1 stop27h 48m

White Plains Westchester County

lör 5/9

12:50 pm-11:09 pm

1 stop10h 19m

$725

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

fre 5/8

2:05 pm-6:00 pm

1 stop27h 55m

White Plains Westchester County

sön 5/10

6:00 am-11:09 pm

1 stop17h 09m

$755

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

fre 5/8

6:13 pm-8:30 pm

1 stop26h 17m

White Plains Westchester County

sön 5/10

12:07 pm-9:12 am

2 stops21h 05m

$814
Cheapest one-way

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

sön 8/16

7:00 am-5:29 pm

2 stops34h 29m

$237

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

sön 7/5

7:00 am-5:29 pm

2 stops34h 29m

$332

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

fre 5/8

6:13 pm-8:30 pm

1 stop26h 17m

$340

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

lör 6/27

5:01 pm-8:59 pm

1 stop27h 58m

$360

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

lör 6/27

5:10 am-10:30 am

1 stop5h 20m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

Showing 1-10 of 15 resultsSorted by cheapest first
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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 4h 30m. American Airlines provides one of the quickest options available for as low as $514. 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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