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Westchester County

$287+ Cheap flights from Portland, ME (PWM) to Westchester County

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HPN
Jul 28 — Aug 41
Mon 7/28
Mon 8/4
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 23, 2025.

Round-trip from

$287
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$214
From Portland to Westchester County
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($45 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 July 2025
Search Deals

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 23, 2025.

This American Airlines deal was found by Cheapflights users on 7/21. 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 8/66:00 amPWM - HPN
1 stop4h 30mAmerican Airlines
Sun 8/106:30 amHPN - PWM
1 stop5h 04mAmerican Airlines
Deal found 7/21$287
This FlightHub deal was found by Cheapflights users on 7/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/103:17 pmPWM - HPN
2 stops20h 04mBreeze Airways
Sun 8/1712:05 pmHPN - PWM
2 stops29h 20mBreeze Airways
Deal found 7/23$1,018

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 23, 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 8/6

6:00 am-10:30 am

1 stop4h 30m

White Plains Westchester County

Sun 8/10

6:30 am-11:34 am

1 stop5h 04m

$287

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Sun 8/10

3:17 pm-11:21 am

2 stops20h 04m

White Plains Westchester County

Sun 8/17

12:05 pm-5:25 pm

2 stops29h 20m

$1,018

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Wed 8/6

6:00 am-10:30 am

1 stop4h 30m

$354

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Wed 7/30

8:07 pm-11:25 am

1 stop15h 18m

$396

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Wed 8/6

12:38 pm-12:30 pm

3 stops23h 52m

$471

PortlandWhite Plains

PWM - HPN

PWMHPN

Portland

Wed 8/6

6:05 am-3:43 pm

2 stops9h 38m

$706

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

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 23, 2025.
See what other customers who have flown with Delta, Breeze Airways, and American Airlines 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
7,967 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

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
7,967 reviews
Delta
8.0
Very good
7,967 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

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
189 reviews
Delta
8.0
Very good
7,967 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

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
7,967 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

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 American Airlines, which is currently one of the cheapest options available, starting at $354. Breeze Airways flights start at $396 while deals on Delta start at $706 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 $287.

  • 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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Top airline flying from Portland to Westchester County

Discover the top airline that operate flights from Portland to Westchester County. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$186Average$276FlexibilityNo cancel feeOn-time71%

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