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Westchester County

$114+ 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
Jun 28 — Jul 51
Sat 6/28
Sat 7/5
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 June 23, 2025.

Round-trip from

$326
(JetBlue)

One-way from

$114
(JetBlue)

Popular in

February

Cheapest in

October

Average price

$197
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 ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 23, 2025.

This JetBlue deal was found by Cheapflights users on 6/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/302:10 pmACK - HPN
Nonstop1h 04mJetBlue
Sun 8/313:59 pmHPN - ACK
Nonstop1h 08mJetBlue
Deal found 6/20$326
This JetBlue deal was found by Cheapflights users on 6/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/107:55 pmBOS - HPN
1 stop26h 37mJetBlue
Mon 7/149:00 pmHPN - BOS
1 stop13h 14mJetBlue
Deal found 6/22$356
This JetBlue deal was found by Cheapflights users on 6/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/283:05 pmBDL - HPN
1 stop8h 26mJetBlue
Sun 8/312:40 pmHPN - BDL
1 stop6h 49mJetBlue
Deal found 6/22$369
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Sat 7/1911:52 amBOS - HPN
2 stops22h 52mAmerican Airlines
Sat 7/266:30 amHPN - BOS
2 stops7h 37mAmerican Airlines
Deal found 6/21$433
This Cape Air deal was found by Cheapflights users on 6/22. 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.
Fri 8/81:53 pmBOS - HPN
1 stop19h 00mCape Air
Sun 8/109:18 amHPN - BOS
1 stop6h 06mCape Air
Deal found 6/22$456
This JetBlue Airways deal was found by Cheapflights users on 6/21. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2112:39 pmBOS - HPN
1 stop4h 12mMultiple Airlines
Sat 7/264:05 pmHPN - BOS
1 stop16h 59mMultiple Airlines
Deal found 6/21$481
This Delta deal was found by Cheapflights users on 6/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:00 amALB - HPN
1 stop12h 07mDelta
Wed 11/510:29 amHPN - ALB
1 stop25h 28mDelta
Deal found 6/22$525
This Gotogate deal was found by Cheapflights users on 6/22. 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.
Mon 8/47:00 amBDL - HPN
3 stops13h 59mBreeze Airways
Wed 8/67:40 pmHPN - BDL
1 stop15h 43mBreeze Airways
Deal found 6/22$541
This Delta deal was found by Cheapflights users on 6/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/293:20 pmMVY - HPN
2 stops24h 29mDelta
Sun 8/315:15 pmHPN - MVY
2 stops18h 03mDelta
Deal found 6/20$548
This JetBlue deal was found by Cheapflights users on 6/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/292:17 pmMVY - HPN
Nonstop1h 20mJetBlue
Sun 8/318:59 amHPN - MVY
1 stop5h 50mJetBlue
Deal found 6/21$590
This American Airlines deal was found by Cheapflights users on 6/20. 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.
Sat 11/18:00 amALB - HPN
2 stops10h 18mAmerican Airlines
Wed 11/56:21 amHPN - ALB
1 stop17h 10mAmerican Airlines
Deal found 6/20$621
This Gotogate deal was found by Cheapflights users on 6/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/269:57 amMVY - HPN
Nonstop1h 20mCape Air
Mon 7/288:44 amHPN - MVY
Nonstop1h 22mCape Air
Deal found 6/21$648

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 June 23, 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

Sat 8/30

2:10 pm-3:14 pm

Nonstop1h 04m

White Plains Westchester County

Sun 8/31

3:59 pm-5:07 pm

Nonstop1h 08m

$326

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Thu 7/10

7:55 pm-10:32 pm

1 stop26h 37m

White Plains Westchester County

Mon 7/14

9:00 pm-10:14 am

1 stop13h 14m

$356

HartfordWhite Plains

BDL - HPN

BDLHPN

Hartford Bradley Intl

Thu 8/28

3:05 pm-11:31 pm

1 stop8h 26m

White Plains Westchester County

Sun 8/31

2:40 pm-9:29 pm

1 stop6h 49m

$369

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Sat 7/19

11:52 am-10:44 am

2 stops22h 52m

White Plains Westchester County

Sat 7/26

6:30 am-2:07 pm

2 stops7h 37m

$433

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Fri 8/8

1:53 pm-8:53 am

1 stop19h 00m

White Plains Westchester County

Sun 8/10

9:18 am-3:24 pm

1 stop6h 06m

$456

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Mon 8/18

6:30 am-8:59 pm

2 stops14h 29m

White Plains Westchester County

Tue 8/19

12:16 pm-11:12 pm

1 stop10h 56m

$485

AlbanyWhite Plains

ALB - HPN

ALBHPN

Albany Intl

Sat 11/1

6:00 am-6:07 pm

1 stop12h 07m

White Plains Westchester County

Wed 11/5

10:29 am-11:57 am

1 stop25h 28m

$525

HartfordWhite Plains

BDL - HPN

BDLHPN

Hartford Bradley Intl

Mon 8/4

7:00 am-8:59 pm

3 stops13h 59m

White Plains Westchester County

Wed 8/6

7:40 pm-11:23 am

1 stop15h 43m

$541

West TisburyWhite Plains

MVY - HPN

MVYHPN

West Tisbury Martha's Vineyard

Fri 8/29

3:20 pm-3:49 pm

2 stops24h 29m

White Plains Westchester County

Sun 8/31

5:15 pm-11:18 am

2 stops18h 03m

$548

West TisburyWhite Plains

MVY - HPN

MVYHPN

West Tisbury Martha's Vineyard

Fri 8/29

2:17 pm-3:37 pm

Nonstop1h 20m

White Plains Westchester County

Sun 8/31

8:59 am-2:49 pm

1 stop5h 50m

$590

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/22

Showing 1-10 of 33 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 June 23, 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 June 23, 2025.
To help decide which airline to fly from Massachusetts to Westchester County, see what other customers have to say about Breeze Airways, Delta and JetBlue. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
182 reviews

Boarding

8.4

Food

6.8

Comfort

8.2

Crew

8.8

Entertainment

6.6

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
182 reviews
Breeze Airways
8.1
Very good
182 reviews

Boarding

8.4

Food

6.8

Comfort

8.2

Crew

8.8

Entertainment

6.6

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,965 reviews
Breeze Airways
8.1
Very good
182 reviews

Boarding

8.4

Food

6.8

Comfort

8.2

Crew

8.8

Entertainment

6.6

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
JetBlue
7.3
Good
2,922 reviews
Breeze Airways
8.1
Very good
182 reviews

Boarding

8.4

Food

6.8

Comfort

8.2

Crew

8.8

Entertainment

6.6

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.1
Very good
182 reviews

Boarding

8.4

Food

6.8

Comfort

8.2

Crew

8.8

Entertainment

6.6

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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 $114. However, be on the lookout for offers from American Airlines and Cape Air, 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 June 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$227Average$243FlexibilityNo cancel feeOn-time62%

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