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$121+ Cheap flights from Westchester County to Maine

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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — PWM
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Cheap flight deals from Westchester County to Maine

Keep the following information in mind while searching for Westchester County to Maine flight deals. Data was last updated November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$253
(American Airlines)

One-way from

$121
(JetBlue)

Popular in

December

Cheapest in

April

Average price

$266
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From Westchester County to Maine
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One-way flight from Westchester County to Maine
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Highest demand for flights based on searches. 10% potential increase in price ($29 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 November 2025
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Find flight deals from Westchester County to Maine

Cheapest flights from Westchester County to Maine
Explore the most affordable flight options available from Westchester County to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 2, 2025.

This American Airlines deal was found by Cheapflights users on 10/30. 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.
Fri 12/125:19 pmHPN - PWM
1 stop6h 18mAmerican Airlines
Fri 12/196:00 amPWM - HPN
1 stop4h 34mAmerican Airlines
Deal found 10/30$253
This American Airlines deal was found by Cheapflights users on 10/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:30 amHPN - PWM
1 stop5h 16mAmerican Airlines
Wed 11/1912:26 pmPWM - HPN
1 stop5h 47mAmerican Airlines
Deal found 10/31$257
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/148:00 amHPN - BOS
1 stop14h 22mMultiple Airlines
Sun 11/168:40 amBOS - HPN
1 stop26h 48mMultiple Airlines
Deal found 11/1$292
This JetBlue deal was found by Cheapflights users on 10/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/157:00 amHPN - BOS
1 stop11h 04mJetBlue
Wed 11/192:15 pmBOS - HPN
1 stop9h 12mJetBlue
Deal found 10/31$315
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/161:19 pmHPN - BOS
1 stop10h 34mMultiple Airlines
Mon 11/179:23 amBOS - HPN
2 stops26h 06mMultiple Airlines
Deal found 11/1$343
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/191:14 pmHPN - BOS
1 stop21h 10mMultiple Airlines
Sat 11/225:45 pmBOS - HPN
2 stops17h 44mMultiple Airlines
Deal found 11/2$358
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/309:23 amHPN - BOS
1 stop22h 55mMultiple Airlines
Sun 12/712:57 pmBOS - HPN
2 stops22h 31mMultiple Airlines
Deal found 10/31$394
This Cape Air deal was found by Cheapflights users on 11/1. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:16 pmHPN - BOS
1 stop15h 02mCape Air
Sat 12/2712:39 pmBOS - HPN
1 stop4h 07mCape Air
Deal found 11/1$395
This JetBlue deal was found by Cheapflights users on 10/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/169:15 amHPN - BOS
1 stop6h 35mJetBlue
Thu 12/1811:45 amBOS - HPN
1 stop8h 40mJetBlue
Deal found 10/31$399
This JetBlue deal was found by Cheapflights users on 11/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:30 amHPN - BOS
1 stop8h 25mJetBlue
Sun 12/72:00 pmBOS - HPN
1 stop8h 00mJetBlue
Deal found 11/1$400
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1512:00 pmHPN - PWM
1 stop22h 09mBreeze Airways
Wed 11/1911:16 amPWM - HPN
2 stops24h 13mBreeze Airways
Deal found 10/31$412
This American Airlines deal was found by Cheapflights users on 10/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:30 amHPN - PWM
1 stop5h 16mAmerican Airlines
Fri 11/2812:26 pmPWM - HPN
1 stop5h 53mAmerican Airlines
Deal found 10/31$447

Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Maine 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 2, 2025.
Use the filters below to find and compare flights from Westchester County to Maine that are best for you.

Fly from

Westchester County

Fly to

Maine

Route

Depart

Return

Price

White PlainsPortland

HPN - PWM

HPNPWM

White Plains Westchester County

Fri 12/12

5:19 pm-11:37 pm

1 stop6h 18m

Portland

Fri 12/19

6:00 am-10:34 am

1 stop4h 34m

$253

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 11/14

8:00 am-10:22 pm

1 stop14h 22m

Boston Logan Intl

Sun 11/16

8:40 am-11:28 am

1 stop26h 48m

$292

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 11/15

7:00 am-6:04 pm

1 stop11h 04m

Boston Logan Intl

Wed 11/19

2:15 pm-11:27 pm

1 stop9h 12m

$315

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sun 11/16

1:19 pm-11:53 pm

1 stop10h 34m

Boston Logan Intl

Mon 11/17

9:23 am-11:29 am

2 stops26h 06m

$343

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 11/19

1:14 pm-10:24 am

1 stop21h 10m

Boston Logan Intl

Sat 11/22

5:45 pm-11:29 am

2 stops17h 44m

$358

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 1/15

9:23 am-3:19 pm

1 stop5h 56m

Boston Logan Intl

Thu 1/15

5:40 pm-8:52 am

1 stop15h 12m

$369

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 12/22

5:16 pm-8:18 am

1 stop15h 02m

Boston Logan Intl

Sat 12/27

12:39 pm-4:46 pm

1 stop4h 07m

$395

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 12/16

9:15 am-3:50 pm

1 stop6h 35m

Boston Logan Intl

Thu 12/18

11:45 am-8:25 pm

1 stop8h 40m

$399

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 12/6

7:30 am-3:55 pm

1 stop8h 25m

Boston Logan Intl

Sun 12/7

2:00 pm-10:00 pm

1 stop8h 00m

$400

White PlainsPortland

HPN - PWM

HPNPWM

White Plains Westchester County

Sat 11/15

12:00 pm-10:09 am

1 stop22h 09m

Portland

Wed 11/19

11:16 am-11:29 am

2 stops24h 13m

$412

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 37 results
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Best time to book a flight from Westchester County to Maine

Have a flexible travel schedule? Discover the best time to fly to Maine from Westchester County 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 Westchester County to Maine

What is the cheapest time of day to fly from REU to ME?

Find hourly flight availability from Westchester County to Maine. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 2, 2025.

It’s optimal to fly from Westchester County to Maine in the evening. By choosing this option you can save up to 36% on the cost of your flight, compared to a flight in the morning.

Related info for your journey

Find useful and relevant information for your journey from Westchester County to Maine. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Westchester County to Maine?

    A quick flight from Westchester County to Maine can take about 6h 18m. American Airlines provides one of the quickest options available for as low as $253. The distance between Westchester County and Maine is about 249 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Westchester County to Maine one-way?

    $121 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Cape Air and Breeze Airways, with prices starting from $264 and $316, respectively.

  • Can I find deals for flights from Westchester County to Maine that include hotel bookings?

    Yes. In addition to deals on Westchester County to Maine flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Westchester County to Maine?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Westchester County to Maine.

  • Can I find deals for business class flights from Westchester County to Maine?

    Yes. Cheapflights offers flight deals from Westchester County to Maine 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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