$110+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — PWM
Apr 22 — Apr 291
Round-trip
1 adult, Economy
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Find cheap flights from Westchester County to Maine with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Westchester County to MaineExplore 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 March 23, 2026.
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 March 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:09 pm
HPN
- BOS
1 stop16h 57m
Multiple Airlines
Mon 5/188:44 am
BOS
- HPN
1 stop8h 45m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$262
This Priceline deal was found by Cheapflights users on 3/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:39 am
HPN
- BOS
1 stop7h 34m
JetBlue
Wed 9/302:10 pm
BOS
- HPN
1 stop8h 38m
JetBlue
Deal found 3/20![JetBlue logo]()
$289
This Priceline deal was found by Cheapflights users on 3/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:23 am
HPN
- BOS
1 stop5h 55m
Multiple Airlines
Tue 4/282:45 pm
BOS
- HPN
1 stop7h 51m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/11:27 pm
HPN
- BOS
1 stop22h 20m
Multiple Airlines
Sat 4/48:48 am
BOS
- HPN
1 stop24h 04m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$349
This Gotogate deal was found by Cheapflights users on 3/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/279:23 am
HPN
- BOS
1 stop22h 47m
Cape Air
Sun 3/298:48 am
BOS
- HPN
1 stop7h 58m
Cape Air
Deal found 3/19![Cape Air logo]()
$353
This Gotogate deal was found by Cheapflights users on 3/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/229:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Tue 3/2412:39 pm
BOS
- HPN
1 stop4h 07m
Cape Air
Deal found 3/18![Cape Air logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 4/186:00 pm
HPN
- BOS
1 stop15h 46m
Multiple Airlines
Tue 4/2112:39 pm
BOS
- HPN
1 stop4h 07m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$373
This Priceline deal was found by Cheapflights users on 3/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/269:23 am
HPN
- BOS
1 stop7h 47m
Multiple Airlines
Tue 4/282:45 pm
BOS
- HPN
1 stop7h 51m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$374
This Cape Air deal was found by Cheapflights users on 3/18. 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.
Sat 3/289:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Mon 3/308:48 am
BOS
- HPN
1 stop24h 04m
Cape Air
Deal found 3/18![Cape Air logo]()
$375
This American Airlines deal was found by Cheapflights users on 3/19. 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 4/16:00 am
HPN
- PWM
1 stop4h 28m
American Airlines
Sat 4/45:29 am
PWM
- HPN
1 stop5h 30m
American Airlines
Deal found 3/19![American Airlines logo]()
$377
This JetBlue deal was found by Cheapflights users on 3/18. 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.
Thu 4/168:05 am
HPN
- BOS
1 stop9h 59m
JetBlue
Thu 4/233:00 pm
BOS
- HPN
1 stop7h 36m
JetBlue
Deal found 3/18![JetBlue logo]()
$378
This American Airlines deal was found by Cheapflights users on 3/20. 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.
Tue 7/215:26 pm
HPN
- PWM
1 stop6h 33m
American Airlines
Sun 7/265:52 am
PWM
- HPN
1 stop4h 38m
American Airlines
Deal found 3/20![American Airlines logo]()
$397
Best flights from Westchester County to MaineDiscover carefully curated flight deals from Westchester County to Maine that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 23, 2026.
Discover carefully curated flight deals from Westchester County to Maine that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 23, 2026.
This Priceline deal was found by Cheapflights users on 3/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:23 am
HPN
- BOS
1 stop5h 55m
Multiple Airlines
Tue 4/282:45 pm
BOS
- HPN
1 stop7h 51m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$344
This JetBlue deal was found by Cheapflights users on 3/18. 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.
Thu 4/168:05 am
HPN
- BOS
1 stop9h 59m
JetBlue
Thu 4/233:00 pm
BOS
- HPN
1 stop7h 36m
JetBlue
Deal found 3/18![JetBlue logo]()
$378
This Booking.com deal was found by Cheapflights users on 3/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/45:16 pm
HPN
- BOS
1 stop14h 54m
Cape Air
Wed 4/82:24 pm
BOS
- HPN
1 stop26h 22m
Cape Air
Deal found 3/20![Cape Air logo]()
$380
This American Airlines deal was found by Cheapflights users on 3/19. 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.
Tue 7/215:26 pm
HPN
- PWM
1 stop6h 33m
American Airlines
Sun 7/265:52 am
PWM
- HPN
1 stop4h 38m
American Airlines
Deal found 3/19![American Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 7/108:00 am
HPN
- PWM
1 stop9h 49m
Breeze Airways
Mon 7/136:29 pm
PWM
- HPN
1 stop16h 58m
Breeze Airways
Deal found 3/22![Breeze Airways logo]()
$573
This Priceline deal was found by Cheapflights users on 3/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/129:23 am
HPN
- BOS
1 stop7h 47m
Multiple Airlines
Tue 4/1412:30 pm
BOS
- HPN
1 stop10h 06m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$364
This Cape Air deal was found by Cheapflights users on 3/20. 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.
Sat 4/115:16 pm
HPN
- BOS
1 stop23h 54m
Cape Air
Mon 4/135:40 pm
BOS
- HPN
1 stop15h 12m
Cape Air
Deal found 3/20![Cape Air logo]()
$395
This Cape Air deal was found by Cheapflights users on 3/21. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/59:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Thu 4/98:48 am
BOS
- HPN
1 stop7h 58m
Cape Air
Deal found 3/21![Cape Air logo]()
$395
This Cape Air deal was found by Cheapflights users on 3/22. 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.
Sat 4/115:16 pm
HPN
- BOS
1 stop18h 42m
Cape Air
Sun 4/122:24 pm
BOS
- HPN
1 stop26h 22m
Cape Air
Deal found 3/22![Cape Air logo]()
$400
This American Airlines deal was found by Cheapflights users on 3/22. 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 6/411:00 am
HPN
- BGR
1 stop6h 19m
American Airlines
Mon 6/85:49 pm
BGR
- HPN
1 stop5h 37m
American Airlines
Deal found 3/22![American Airlines logo]()
$523
This Cape Air deal was found by Cheapflights users on 3/22. 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.
Sun 4/129:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Sat 4/182:24 pm
BOS
- HPN
1 stop26h 22m
Cape Air
Deal found 3/22![Cape Air logo]()
$415
This Cape Air deal was found by Cheapflights users on 3/19. 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.
Wed 5/275:16 pm
HPN
- BOS
1 stop14h 54m
Cape Air
Sun 5/3112:39 pm
BOS
- HPN
1 stop4h 07m
Cape Air
Deal found 3/19![Cape Air logo]()
$415
This KAYAK deal was found by Cheapflights users on 3/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:40 pm
HPN
- PWM
1 stop20h 44m
Breeze Airways
Sun 9/137:00 am
PWM
- HPN
2 stops28h 20m
Breeze Airways
Deal found 3/21![Breeze Airways logo]()
$644
This American Airlines deal was found by Cheapflights users on 3/20. 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 6/2511:00 am
HPN
- PWM
1 stop5h 24m
American Airlines
Tue 6/305:38 am
PWM
- HPN
1 stop4h 52m
American Airlines
Deal found 3/20![American Airlines logo]()
$595
This Cape Air deal was found by Cheapflights users on 3/19. 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.
Sun 4/129:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Tue 4/148:48 am
BOS
- HPN
1 stop7h 58m
Cape Air
Deal found 3/19![Cape Air logo]()
$415
This American Airlines deal was found by Cheapflights users on 3/18. 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 4/25:30 pm
HPN
- BGR
1 stop6h 23m
American Airlines
Mon 4/65:15 am
BGR
- HPN
1 stop5h 44m
American Airlines
Deal found 3/18![American Airlines logo]()
$597
This Cape Air deal was found by Cheapflights users on 3/19. 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.
Sun 5/35:16 pm
HPN
- BOS
1 stop22h 02m
Cape Air
Sun 5/105:40 pm
BOS
- HPN
1 stop23h 06m
Cape Air
Deal found 3/19![Cape Air logo]()
$415
This American Airlines deal was found by Cheapflights users on 3/19. 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 4/911:00 am
HPN
- BGR
1 stop5h 29m
American Airlines
Thu 4/1612:59 pm
BGR
- HPN
1 stop7h 28m
American Airlines
Deal found 3/19![American Airlines logo]()
$597
This KAYAK deal was found by Cheapflights users on 3/18. 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.
Fri 5/296:09 pm
HPN
- PWM
1 stop22h 07m
Breeze Airways
Tue 6/23:16 pm
PWM
- HPN
2 stops29h 14m
Breeze Airways
Deal found 3/18![Breeze Airways logo]()
$742
This Booking.com deal was found by Cheapflights users on 3/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2112:27 pm
HPN
- PWM
2 stops22h 00m
Breeze Airways
Sun 7/267:00 am
PWM
- HPN
2 stops13h 59m
Breeze Airways
Deal found 3/19![Breeze Airways logo]()
$749
This Cape Air deal was found by Cheapflights users on 3/21. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/65:16 pm
HPN
- AUG
2 stops41h 12m
Cape Air
Fri 4/1011:23 am
AUG
- HPN
2 stops21h 29m
Cape Air
Deal found 3/21![Cape Air logo]()
$564
This American Airlines deal was found by Cheapflights users on 3/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:00 am
HPN
- BGR
1 stop5h 29m
American Airlines
Thu 4/1612:59 pm
BGR
- HPN
1 stop5h 29m
American Airlines
Deal found 3/23![American Airlines logo]()
$751
This KAYAK deal was found by Cheapflights users on 3/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:00 pm
HPN
- PWM
3 stops31h 42m
Breeze Airways
Mon 9/79:52 am
PWM
- HPN
2 stops25h 35m
Breeze Airways
Deal found 3/21![Breeze Airways logo]()
$860
This Cape Air deal was found by Cheapflights users on 3/19. 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.
Tue 4/219:23 am
HPN
- AUG
2 stops25h 05m
Cape Air
Sat 4/257:55 am
AUG
- HPN
2 stops24h 57m
Cape Air
Deal found 3/19![Cape Air logo]()
$564
This American Airlines deal was found by Cheapflights users on 3/20. 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.
Mon 6/225:29 pm
HPN
- BGR
1 stop6h 30m
American Airlines
Fri 6/265:20 pm
BGR
- HPN
1 stop6h 06m
American Airlines
Deal found 3/20![American Airlines logo]()
$831
This Cape Air deal was found by Cheapflights users on 3/18. 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.
Fri 5/299:23 am
HPN
- AUG
2 stops26h 28m
Cape Air
Tue 6/23:29 pm
AUG
- HPN
2 stops25h 17m
Cape Air
Deal found 3/18![Cape Air logo]()
$623
This American Airlines deal was found by Cheapflights users on 3/20. 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 7/296:59 pm
HPN
- BGR
1 stop18h 29m
American Airlines
Sat 8/17:00 am
BGR
- HPN
2 stops13h 09m
American Airlines
Deal found 3/20![American Airlines logo]()
$832
This Cape Air deal was found by Cheapflights users on 3/18. 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.
Tue 5/59:23 am
HPN
- AUG
2 stops9h 27m
Cape Air
Wed 5/67:55 am
AUG
- HPN
2 stops24h 57m
Cape Air
Deal found 3/18![Cape Air logo]()
$623
This American Airlines deal was found by Cheapflights users on 3/22. 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 7/103:23 pm
HPN
- PWM
2 stops17h 59m
American Airlines
Mon 7/1310:01 am
PWM
- HPN
2 stops13h 26m
American Airlines
Deal found 3/22![American Airlines logo]()
$864
This Cape Air deal was found by Cheapflights users on 3/19. 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.
Fri 4/39:23 am
HPN
- AUG
2 stops33h 27m
Cape Air
Tue 4/73:29 pm
AUG
- HPN
2 stops49h 17m
Cape Air
Deal found 3/19![Cape Air logo]()
$624
Last-minute flights from Westchester County to MaineDiscover last-minute flight deals from Westchester County to Maine. Data last updated March 23, 2026 and is based on user searches.
Discover last-minute flight deals from Westchester County to Maine. Data last updated March 23, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 3/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/229:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Tue 3/2412:39 pm
BOS
- HPN
1 stop4h 07m
Cape Air
Deal found 3/18![Cape Air logo]()
$364
This Cape Air deal was found by Cheapflights users on 3/20. 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.
Tue 3/245:16 pm
HPN
- BOS
1 stop22h 02m
Cape Air
Thu 3/268:48 am
BOS
- HPN
1 stop7h 58m
Cape Air
Deal found 3/20![Cape Air logo]()
$385
This Gotogate deal was found by Cheapflights users on 3/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/269:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Sat 3/288:48 am
BOS
- HPN
1 stop7h 58m
Cape Air
Deal found 3/22![Cape Air logo]()
$379
This Gotogate deal was found by Cheapflights users on 3/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/279:23 am
HPN
- BOS
1 stop22h 47m
Cape Air
Sun 3/298:48 am
BOS
- HPN
1 stop7h 58m
Cape Air
Deal found 3/19![Cape Air logo]()
$353
This Cape Air deal was found by Cheapflights users on 3/18. 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.
Sat 3/289:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Mon 3/308:48 am
BOS
- HPN
1 stop24h 04m
Cape Air
Deal found 3/18![Cape Air logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/11:27 pm
HPN
- BOS
1 stop22h 20m
Multiple Airlines
Sat 4/48:48 am
BOS
- HPN
1 stop24h 04m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 3/19. 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 4/16:00 am
HPN
- PWM
1 stop4h 28m
American Airlines
Sat 4/45:29 am
PWM
- HPN
1 stop5h 30m
American Airlines
Deal found 3/19![American Airlines logo]()
$377
This American Airlines deal was found by Cheapflights users on 3/19. 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 4/15:30 pm
HPN
- PWM
1 stop6h 25m
American Airlines
Wed 4/156:00 am
PWM
- HPN
1 stop4h 30m
American Airlines
Deal found 3/19![American Airlines logo]()
$519
This JetBlue deal was found by Cheapflights users on 3/18. 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.
Thu 4/168:05 am
HPN
- BOS
1 stop9h 59m
JetBlue
Thu 4/233:00 pm
BOS
- HPN
1 stop7h 36m
JetBlue
Deal found 3/18![JetBlue logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 4/186:00 pm
HPN
- BOS
1 stop15h 46m
Multiple Airlines
Tue 4/2112:39 pm
BOS
- HPN
1 stop4h 07m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$373
This Priceline deal was found by Cheapflights users on 3/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:23 am
HPN
- BOS
1 stop5h 55m
Multiple Airlines
Tue 4/282:45 pm
BOS
- HPN
1 stop7h 51m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$344
This Priceline deal was found by Cheapflights users on 3/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/269:23 am
HPN
- BOS
1 stop7h 47m
Multiple Airlines
Tue 4/282:45 pm
BOS
- HPN
1 stop7h 51m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$374
One-way flights from Westchester County to MaineSearch for one-way flight options from Westchester County to Maine. Find affordable one-way fares based on user searches. Data last updated March 23, 2026.
Search for one-way flight options from Westchester County to Maine. Find affordable one-way fares based on user searches. Data last updated March 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/22. 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.
Tue 6/91:29 pm
HPN
- BOS
1 stop21h 36m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$110
This Cape Air deal was found by Cheapflights users on 3/20. 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.
Sat 3/289:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Deal found 3/20![Cape Air logo]()
$190
This Cape Air deal was found by Cheapflights users on 3/18. 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.
Sat 4/45:16 pm
HPN
- BOS
1 stop14h 54m
Cape Air
Deal found 3/18![Cape Air logo]()
$200
This Mytrip deal was found by Cheapflights users on 3/18. 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 4/249:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Deal found 3/18![Cape Air logo]()
$208
This Priceline deal was found by Cheapflights users on 3/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Deal found 3/19![Cape Air logo]()
$210
This Cape Air deal was found by Cheapflights users on 3/18. 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.
Thu 4/29:23 am
HPN
- BOS
1 stop7h 47m
Cape Air
Deal found 3/18![Cape Air logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 4/11:27 pm
HPN
- BOS
1 stop22h 20m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 4/221:27 pm
HPN
- BOS
2 stops36h 04m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 5/108:00 am
HPN
- BOS
3 stops39h 44m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$227
This Cape Air deal was found by Cheapflights users on 3/18. 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.
Thu 7/99:26 am
HPN
- BOS
1 stop5h 57m
Cape Air
Deal found 3/18![Cape Air logo]()
$230
This Cape Air deal was found by Cheapflights users on 3/21. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:23 am
HPN
- AUG
2 stops25h 05m
Cape Air
Deal found 3/21![Cape Air logo]()
$264
This Cape Air deal was found by Cheapflights users on 3/19. 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.
Sun 3/299:23 am
HPN
- AUG
2 stops28h 56m
Cape Air
Deal found 3/19![Cape Air logo]()
$284
Find 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 March 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $262 (Kiwi.com) |
One-way from | $146 (Kiwi.com) |
Popular in | December |
Cheapest in | April |
Average price | $295 |
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 March 23, 2026.
Use the filters below to find and compare flights from Westchester County to Maine that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Tue 4/21
9:23 am-3:18 pm
1 stop5h 55m
Boston Logan Intl
Tue 4/28
2:45 pm-10:36 pm
1 stop7h 51m
$344
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Sun 4/12
9:23 am-5:10 pm
1 stop7h 47m
Boston Logan Intl
Tue 4/14
12:30 pm-10:36 pm
1 stop10h 06m
$364
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Thu 4/16
8:05 am-6:04 pm
1 stop9h 59m
Boston Logan Intl
Thu 4/23
3:00 pm-10:36 pm
1 stop7h 36m
$378
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Sat 4/4
5:16 pm-8:10 am
1 stop14h 54m
Boston Logan Intl
Wed 4/8
2:24 pm-4:46 pm
1 stop26h 22m
$380
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Sat 4/11
5:16 pm-5:10 pm
1 stop23h 54m
Boston Logan Intl
Mon 4/13
5:40 pm-8:52 am
1 stop15h 12m
$395
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Sun 4/5
9:23 am-5:10 pm
1 stop7h 47m
Boston Logan Intl
Thu 4/9
8:48 am-4:46 pm
1 stop7h 58m
$395
White PlainsPortland
HPN - PWM
HPNPWM
White Plains Westchester County
Tue 7/21
5:26 pm-11:59 pm
1 stop6h 33m
Portland
Sun 7/26
5:52 am-10:30 am
1 stop4h 38m
$397
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Sat 4/11
5:16 pm-11:58 am
1 stop18h 42m
Boston Logan Intl
Sun 4/12
2:24 pm-4:46 pm
1 stop26h 22m
$400
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Sun 4/12
9:23 am-5:10 pm
1 stop7h 47m
Boston Logan Intl
Sat 4/18
2:24 pm-4:46 pm
1 stop26h 22m
$415
White PlainsBoston
HPN - BOS
HPNBOS
White Plains Westchester County
Wed 5/27
5:16 pm-8:10 am
1 stop14h 54m
Boston Logan Intl
Sun 5/31
12:39 pm-4:46 pm
1 stop4h 07m
$415
Showing 1-10 of 55 resultsSorted by cheapest first
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.
HPN-BOS
HPN-PWM
HPN-BGR
HPN-AUG
HPN-BHB
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
zzREU-USME
HPN-BOS
HPN-PWM
HPN-BGR
HPN-AUG
No data available for this route at this time. Please check back soon.
Related info for your journey
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