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Westchester County

$298+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HPN
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$307
(American Airlines)

One-way from

$298
(Expedia)

Popular in

February

Cheapest in

September

Average price

$217
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 ($45 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 July 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 July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 10/305:21 pmPWM - HPN
1 stop6h 07mAmerican Airlines
Sat 11/111:04 amHPN - PWM
1 stop5h 13mAmerican Airlines
Deal found 7/30$307
This Expedia deal was found by Cheapflights users on 7/31. 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 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
Fri 9/267:30 amHPN - PWM
2 stops14h 37mJetBlue
Deal found 7/31$334
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 9/191:35 pmPWM - HPN
1 stop22h 24mDelta
Sat 9/205:20 pmHPN - PWM
1 stop18h 35mDelta
Deal found 7/29$615
This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/229:46 amPWM - HPN
2 stops25h 43mBreeze Airways
Fri 9/2612:10 pmHPN - PWM
1 stop25h 31mBreeze Airways
Deal found 7/31$620
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/226:05 pmPWM - HPN
3 stops26h 25mMultiple Airlines
Tue 9/21:29 pmHPN - PWM
2 stops28h 09mMultiple Airlines
Deal found 7/29$1,031

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 July 31, 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

6:00 am-10:34 am

1 stop4h 34m

White Plains Westchester County

Sat 11/1

3:00 pm-9:18 pm

1 stop6h 18m

$307

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Mon 9/22

7:09 am-10:48 pm

2 stops15h 39m

White Plains Westchester County

Fri 9/26

7:30 am-10:07 pm

2 stops14h 37m

$334

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Fri 9/19

1:35 pm-11:59 am

1 stop22h 24m

White Plains Westchester County

Sat 9/20

5:20 pm-11:55 am

1 stop18h 35m

$615

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Mon 9/22

9:46 am-11:29 am

2 stops25h 43m

White Plains Westchester County

Fri 9/26

12:10 pm-1:41 pm

1 stop25h 31m

$620

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Fri 8/22

6:05 pm-8:30 pm

3 stops26h 25m

White Plains Westchester County

Tue 9/2

1:29 pm-5:38 pm

2 stops28h 09m

$1,031

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Thu 8/14

6:05 am-10:31 pm

2 stops16h 26m

$298

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Wed 8/6

5:16 pm-11:25 pm

1 stop6h 09m

$354

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Wed 8/6

8:07 pm-11:25 am

1 stop15h 18m

$372

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Thu 8/14

3:17 pm-11:21 am

3 stops20h 04m

$505

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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.

Reviews of airlines servicing Westchester County

Get insights into the airlines that provide service to Westchester County. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Westchester County. Reviews last updated July 31, 2025.
See what other customers who have flown with Delta, Breeze Airways, and JetBlue from Portland to Westchester County have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
Breeze Airways
8.0
Very good
191 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
JetBlue
7.3
Good
2,914 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!

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.

  • 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 $298. American Airlines flights start at $354 while deals on Breeze Airways start at $372 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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