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Westchester County

$124+ 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 7/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HPN
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheap 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 May 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$227
(JetBlue)

One-way from

$124
(JetBlue)

Popular in

April

Cheapest in

October

Average price

$172
Provider with most accurate pricing for Boston Logan Intl-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-New York (NYC) flights.
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From Massachusetts to Westchester County
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One-way flight from Massachusetts to Westchester County
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Highest demand for flights based on searches. 18% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Find 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 May 1, 2025.

This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/236:01 pmACK - HPN
Nonstop0h 59mJetBlue
Tue 5/278:59 amHPN - ACK
Nonstop1h 01mJetBlue
Deal found 4/30$227
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/133:05 pmBDL - HPN
1 stop6h 55mJetBlue
Tue 5/207:00 amHPN - BDL
1 stop9h 29mJetBlue
Deal found 4/29$373
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2811:45 amBOS - HPN
1 stop11h 15mJetBlue
Wed 6/49:00 amHPN - BOS
1 stop7h 05mJetBlue
Deal found 4/29$388
This Cape Air deal was found by Cheapflights users on 4/30. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/308:35 amBOS - HPN
1 stop24h 17mCape Air
Sun 6/19:20 amHPN - BOS
1 stop22h 44mCape Air
Deal found 4/30$416
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/296:10 amBOS - HPN
2 stops38h 49mMultiple Airlines
Sun 6/18:10 amHPN - BOS
1 stop10h 42mMultiple Airlines
Deal found 4/30$441
This American Airlines deal was found by Cheapflights users on 4/30. 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 6/135:30 amBOS - HPN
1 stop9h 10mAmerican Airlines
Mon 6/1611:05 amHPN - BOS
2 stops9h 23mAmerican Airlines
Deal found 4/30$547
This Gotogate deal was found by Cheapflights users on 4/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/231:51 pmACK - HPN
2 stops19h 01mCape Air
Tue 5/279:20 amHPN - ACK
2 stops7h 30mCape Air
Deal found 4/30$844
This Gotogate deal was found by Cheapflights users on 4/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/231:51 pmACK - HPN
2 stops19h 01mMultiple Airlines
Tue 5/278:10 amHPN - ACK
Nonstop0h 58mMultiple Airlines
Deal found 4/30$961
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 6/225:26 pmACK - HPN
1 stop5h 57mAmerican Airlines
Tue 6/246:30 amHPN - ACK
1 stop34h 26mAmerican Airlines
Deal found 4/30$1,191

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 May 1, 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

NantucketWhite Plains

ACK - HPN

ACKHPN

Nantucket Memorial

Fri 5/23

6:01 pm-7:00 pm

Nonstop0h 59m

White Plains Westchester County

Tue 5/27

8:59 am-10:00 am

Nonstop1h 01m

$227

HartfordWhite Plains

BDL - HPN

BDLHPN

Hartford Bradley Intl

Tue 5/13

3:05 pm-10:00 pm

1 stop6h 55m

White Plains Westchester County

Tue 5/20

7:00 am-4:29 pm

1 stop9h 29m

$373

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Wed 5/28

11:45 am-11:00 pm

1 stop11h 15m

White Plains Westchester County

Wed 6/4

9:00 am-4:05 pm

1 stop7h 05m

$388

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Fri 5/30

8:35 am-8:52 am

1 stop24h 17m

White Plains Westchester County

Sun 6/1

9:20 am-8:04 am

1 stop22h 44m

$416

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Thu 5/29

6:10 am-8:59 pm

2 stops38h 49m

White Plains Westchester County

Sun 6/1

8:10 am-6:52 pm

1 stop10h 42m

$441

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Fri 6/13

5:30 am-2:40 pm

1 stop9h 10m

White Plains Westchester County

Mon 6/16

11:05 am-8:28 pm

2 stops9h 23m

$547

NantucketWhite Plains

ACK - HPN

ACKHPN

Nantucket Memorial

Fri 5/23

1:51 pm-8:52 am

2 stops19h 01m

White Plains Westchester County

Tue 5/27

9:20 am-4:50 pm

2 stops7h 30m

$844

NantucketWhite Plains

ACK - HPN

ACKHPN

Nantucket Memorial

Fri 5/23

1:51 pm-8:52 am

2 stops19h 01m

White Plains Westchester County

Tue 5/27

8:10 am-9:08 am

Nonstop0h 58m

$961

NantucketWhite Plains

ACK - HPN

ACKHPN

Nantucket Memorial

Sun 6/22

5:26 pm-11:23 pm

1 stop5h 57m

White Plains Westchester County

Tue 6/24

6:30 am-4:56 pm

1 stop34h 26m

$1,191

NantucketWhite Plains

ACK - HPN

ACKHPN

Nantucket Memorial

Wed 7/30

2:10 pm-3:14 pm

Nonstop1h 04m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 20 results
1
2

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 May 1, 2025.

When flying from Massachusetts to Westchester County, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 May 1, 2025.
To help decide which airline to fly from Massachusetts to Westchester County, see what other customers have to say about Delta, JetBlue and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

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
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

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
2,924 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

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
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

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 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.

  • 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 $124. However, be on the lookout for offers from Cape Air and Delta, 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.

  • What is the cheapest month to book a flight from Massachusetts to Westchester County?

    Currently, January is the cheapest month in which you can book a flight from Massachusetts to Westchester County (average of $276). Flying from Massachusetts 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.

See more FAQs

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$176Average$228FlexibilityNo cancel feeOn-time62%

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