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Westchester County

$96+ Cheap flights from Massachusetts 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HPN
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Massachusetts to Westchester County

Cheapest flights from Massachusetts to Westchester County
Explore the most affordable flight options available from Massachusetts to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Cape Air deal was found by Cheapflights users on 12/15. 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 12/318:48 amBOS - HPN
1 stop24h 04mCape Air
Sat 1/35:16 pmHPN - BOS
1 stop22h 02mCape Air
Deal found 12/15$375
This Cape Air deal was found by Cheapflights users on 12/17. 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 12/248:48 amBOS - HPN
1 stop24h 04mCape Air
Sat 12/275:16 pmHPN - BOS
1 stop18h 42mCape Air
Deal found 12/17$395
This Cape Air deal was found by Cheapflights users on 12/15. 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 12/302:24 pmBOS - HPN
1 stop18h 28mCape Air
Sun 1/45:16 pmHPN - BOS
1 stop23h 54mCape Air
Deal found 12/15$415
This Cape Air deal was found by Cheapflights users on 12/15. 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 12/292:24 pmBOS - HPN
1 stop18h 28mCape Air
Thu 1/19:23 amHPN - BOS
1 stop22h 47mCape Air
Deal found 12/15$435
This Cape Air deal was found by Cheapflights users on 12/16. 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 12/222:24 pmBOS - HPN
1 stop18h 28mCape Air
Sun 12/285:16 pmHPN - BOS
1 stop18h 42mCape Air
Deal found 12/16$445
This Cape Air deal was found by Cheapflights users on 12/16. 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 12/218:48 amBOS - HPN
1 stop7h 58mCape Air
Sun 12/285:16 pmHPN - BOS
1 stop22h 02mCape Air
Deal found 12/16$455
This Cape Air deal was found by Cheapflights users on 12/16. 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 12/2212:39 pmBOS - HPN
1 stop20h 13mCape Air
Sat 12/279:23 amHPN - BOS
1 stop7h 47mCape Air
Deal found 12/16$465
This Cape Air deal was found by Cheapflights users on 12/15. 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 12/2912:39 pmBOS - HPN
1 stop20h 13mCape Air
Tue 12/305:16 pmHPN - BOS
1 stop14h 54mCape Air
Deal found 12/15$475
This Cape Air deal was found by Cheapflights users on 12/16. 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 12/178:48 amBOS - HPN
1 stop7h 58mCape Air
Wed 12/249:23 amHPN - BOS
1 stop22h 47mCape Air
Deal found 12/16$485
This Cape Air deal was found by Cheapflights users on 12/16. 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 12/178:48 amBOS - HPN
1 stop24h 04mCape Air
Tue 12/235:16 pmHPN - BOS
1 stop14h 54mCape Air
Deal found 12/16$505
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/3110:56 amBOS - HPN
2 stops24h 33mMultiple Airlines
Sun 1/49:23 amHPN - BOS
1 stop5h 55mMultiple Airlines
Deal found 12/16$568
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Thu 12/1810:47 amBOS - HPN
1 stop24h 41mMultiple Airlines
Mon 12/228:00 amHPN - BOS
2 stops50h 50mMultiple Airlines
Deal found 12/17$620

Find flight deals from Massachusetts to Westchester County

Keep the following information in mind while searching for Massachusetts to Westchester County flight deals. Data was last updated December 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$236
(Kiwi.com)

One-way from

$96
(Kiwi.com)

Popular in

February

Cheapest in

November

Average price

$192
Provider with most accurate pricing for Boston Logan Intl-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-New York (NYC) flights.
Search Deals
From Massachusetts to Westchester County
Search Deals
One-way flight from Massachusetts to Westchester County
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts 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 December 18, 2025.
Use the filters below to find and compare flights from Massachusetts to Westchester County that are best for you.

Fly from

Massachusetts

Fly to

Westchester County

Route

Depart

Return

Price

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Sat 1/31

11:40 am-6:31 pm

1 stop6h 51m

White Plains Westchester County

Tue 2/3

1:00 pm-11:48 pm

1 stop10h 48m

$296

AlbanyWhite Plains

ALB - HPN

ALBHPN

Albany Intl

Thu 1/1

1:20 pm-11:28 am

1 stop22h 08m

White Plains Westchester County

Mon 1/5

8:00 am-8:56 pm

1 stop12h 56m

$301

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Mon 1/19

7:00 am-2:03 pm

1 stop7h 03m

White Plains Westchester County

Thu 1/22

9:23 am-5:10 pm

1 stop7h 47m

$331

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Tue 1/13

7:00 am-2:03 pm

1 stop7h 03m

White Plains Westchester County

Tue 1/20

1:00 pm-11:48 pm

1 stop10h 48m

$350

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Thu 1/1

10:47 am-11:28 am

1 stop24h 41m

White Plains Westchester County

Mon 1/5

12:10 pm-10:01 am

2 stops21h 51m

$352

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Sun 1/11

2:15 pm-11:01 pm

1 stop8h 46m

White Plains Westchester County

Tue 1/13

7:00 am-2:50 pm

1 stop7h 50m

$373

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Fri 1/2

8:48 am-8:52 am

1 stop24h 04m

White Plains Westchester County

Sat 1/3

5:16 pm-3:18 pm

1 stop22h 02m

$375

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Fri 1/9

8:48 am-8:52 am

1 stop24h 04m

White Plains Westchester County

Mon 1/12

9:23 am-5:10 pm

1 stop7h 47m

$375

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Mon 1/5

5:40 pm-8:52 am

1 stop15h 12m

White Plains Westchester County

Thu 1/15

9:23 am-5:10 pm

1 stop7h 47m

$375

HartfordWhite Plains

BDL - HPN

BDLHPN

Hartford Bradley Intl

Wed 1/14

3:20 pm-11:01 pm

1 stop7h 41m

White Plains Westchester County

Wed 1/21

8:15 am-5:27 pm

1 stop9h 12m

$380

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 49 results
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Best time to book a flight from Massachusetts to Westchester County

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

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

Find hourly flight availability from Massachusetts to Westchester County. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 65% on flights from Massachusetts to Westchester County by exploring options for tickets at noon.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Westchester County. 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 Massachusetts to Westchester County?

    There are many flights that can get you from Massachusetts to Westchester County in 6h 51m. Fly via JetBlue to get the fastest option. The distance from Massachusetts to Westchester County is about 165 mi.

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

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $123. However, be on the lookout for offers from Cape Air and Tradewind, as they are both options that can get you from Massachusetts to Westchester County for a low price.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Massachusetts 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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Alternative routes for Massachusetts to Westchester County

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Massachusetts to Westchester County

Discover the top airline that operate flights from Massachusetts 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$156Average$351FlexibilityNo cancel feeOn-time62%

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