HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HPN
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Westchester County 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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 14, 2025.

Round-trip from

$227
(Priceline)

One-way from

$124
(JetBlue)

Popular in

February

Cheapest in

October

Average price

$186
From Massachusetts to Westchester County
Search Deals
One-way flight from Massachusetts to Westchester County
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 14, 2025.

This Priceline deal was found by Cheapflights users on 8/13. 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.
Wed 9/32:26 pmACK - HPN
Nonstop1h 01mJetBlue
Sun 9/78:59 amHPN - ACK
Nonstop1h 01mJetBlue
Deal found 8/13$227
This Priceline deal was found by Cheapflights users on 8/14. 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.
Thu 9/112:20 pmBOS - HPN
1 stop7h 56mJetBlue
Thu 9/187:30 amHPN - BOS
1 stop11h 16mJetBlue
Deal found 8/14$253
This JetBlue deal was found by Cheapflights users on 8/13. 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 8/296:26 pmACK - HPN
Nonstop1h 04mJetBlue
Sun 8/318:56 amHPN - ACK
Nonstop1h 04mJetBlue
Deal found 8/13$257
This Priceline deal was found by Cheapflights users on 8/14. 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.
Wed 9/102:20 pmBOS - HPN
1 stop7h 56mJetBlue
Thu 9/119:39 amHPN - BOS
1 stop10h 21mJetBlue
Deal found 8/14$266
This JetBlue deal was found by Cheapflights users on 8/14. 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 9/262:20 pmBOS - HPN
1 stop7h 56mJetBlue
Mon 9/297:30 amHPN - BOS
1 stop11h 16mJetBlue
Deal found 8/14$273
This Priceline deal was found by Cheapflights users on 8/14. 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 9/302:20 pmBOS - HPN
1 stop8h 11mJetBlue
Wed 10/19:39 amHPN - BOS
1 stop10h 26mJetBlue
Deal found 8/14$276
This Priceline deal was found by Cheapflights users on 8/13. 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.
Wed 10/159:55 amBOS - HPN
1 stop11h 35mJetBlue
Sat 10/257:30 amHPN - BOS
1 stop8h 50mJetBlue
Deal found 8/13$297
This JetBlue deal was found by Cheapflights users on 8/13. 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 9/273:30 pmBDL - HPN
1 stop6h 46mJetBlue
Sat 10/41:00 pmHPN - BDL
1 stop7h 33mJetBlue
Deal found 8/13$298
This JetBlue deal was found by Cheapflights users on 8/13. 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 12/32:00 pmBOS - HPN
1 stop7h 30mJetBlue
Mon 12/81:00 pmHPN - BOS
1 stop7h 15mJetBlue
Deal found 8/13$326
This JetBlue deal was found by Cheapflights users on 8/13. 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 9/191:44 pmBDL - HPN
1 stop8h 32mJetBlue
Fri 9/269:00 amHPN - BDL
1 stop8h 13mJetBlue
Deal found 8/13$354
This Cape Air deal was found by Cheapflights users on 8/13. 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 12/46:10 pmBOS - HPN
1 stop22h 42mCape Air
Mon 12/85:20 pmHPN - BOS
1 stop20h 39mCape Air
Deal found 8/13$396
This Booking.com deal was found by Cheapflights users on 8/14. 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 11/2512:40 pmBOS - HPN
1 stop20h 12mCape Air
Sun 11/305:20 pmHPN - BOS
1 stop17h 39mCape Air
Deal found 8/14$400

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 August 14, 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

Wed 9/3

2:26 pm-3:27 pm

Nonstop1h 01m

White Plains Westchester County

Sun 9/7

8:59 am-10:00 am

Nonstop1h 01m

$227

NantucketWhite Plains

ACK - HPN

ACKHPN

Nantucket Memorial

Thu 9/4

2:16 pm-3:17 pm

Nonstop1h 01m

White Plains Westchester County

Sun 9/7

8:59 am-10:00 am

Nonstop1h 01m

$227

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Thu 9/11

2:20 pm-10:16 pm

1 stop7h 56m

White Plains Westchester County

Thu 9/18

7:30 am-6:46 pm

1 stop11h 16m

$253

NantucketWhite Plains

ACK - HPN

ACKHPN

Nantucket Memorial

Thu 8/28

6:26 pm-7:30 pm

Nonstop1h 04m

White Plains Westchester County

Mon 9/1

3:59 pm-5:07 pm

Nonstop1h 08m

$257

NantucketWhite Plains

ACK - HPN

ACKHPN

Nantucket Memorial

Fri 8/29

2:10 pm-3:14 pm

Nonstop1h 04m

White Plains Westchester County

Sun 8/31

8:56 am-10:00 am

Nonstop1h 04m

$257

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Wed 9/10

2:20 pm-10:16 pm

1 stop7h 56m

White Plains Westchester County

Thu 9/11

9:39 am-8:00 pm

1 stop10h 21m

$266

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Fri 9/26

2:20 pm-10:16 pm

1 stop7h 56m

White Plains Westchester County

Mon 9/29

7:30 am-6:46 pm

1 stop11h 16m

$273

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Tue 9/30

2:20 pm-10:31 pm

1 stop8h 11m

White Plains Westchester County

Wed 10/1

9:39 am-8:05 pm

1 stop10h 26m

$276

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Wed 10/15

9:55 am-9:30 pm

1 stop11h 35m

White Plains Westchester County

Sat 10/25

7:30 am-4:20 pm

1 stop8h 50m

$297

HartfordWhite Plains

BDL - HPN

BDLHPN

Hartford Bradley Intl

Sat 9/27

3:30 pm-10:16 pm

1 stop6h 46m

White Plains Westchester County

Sat 10/4

1:00 pm-8:33 pm

1 stop7h 33m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 60 results
1
2
3
...
6

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 August 14, 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.

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.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Westchester County

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
Dallas/Fort Worth to LaGuardia flights
San Francisco to John F Kennedy Intl flights
Dallas/Fort Worth to John F Kennedy Intl flights
Los Angeles to Newark flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
San Francisco to Newark flights
Dallas/Fort Worth to Newark flights
Los Angeles to LaGuardia flights
Atlanta to LaGuardia flights
Fort Lauderdale to LaGuardia flights
Hobby to LaGuardia flights
Atlanta to John F Kennedy Intl flights
Miami to LaGuardia flights
San Francisco to LaGuardia flights
Fort Lauderdale to Newark flights
Denver to John F Kennedy Intl flights
Fort Lauderdale to John F Kennedy Intl flights
Miami to Newark flights
Miami to John F Kennedy Intl flights
Ontario to John F Kennedy Intl flights
Orlando to John F Kennedy Intl flights
Seattle to John F Kennedy Intl flights
Tampa to John F Kennedy Intl flights
Sky Harbor Intl to John F Kennedy Intl flights
Orlando to LaGuardia flights
Denver to LaGuardia flights
Atlanta to Newark flights
Hobby to John F Kennedy Intl flights
Burbank to Newark flights
Tampa to Newark flights
Tampa to LaGuardia flights
Hobby to Newark flights
Ontario to Newark flights
Minneapolis to LaGuardia flights
Orlando to Newark flights
Midway to LaGuardia flights
Seattle to Newark flights
Denver to Newark flights
Raleigh to LaGuardia flights
George Bush Intcntl to Newark flights
George Bush Intcntl to LaGuardia flights
Santa Ana to Newark flights
San Diego to John F Kennedy Intl flights
George Bush Intcntl to John F Kennedy Intl flights
Sky Harbor Intl to Newark flights
San Diego to Newark flights
Midway to Newark flights

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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$176Average$280FlexibilityNo cancel feeOn-time62%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.