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Westchester County

$185+ Cheap flights from Boston (BOS) 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 12/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HPN
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
1 adult, Economy
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Cheap flight deals from Boston to Westchester County

Cheapest flights from Boston to Westchester County
Explore the most affordable flight options available from Boston to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 12, 2025.

This Cape Air deal was found by Cheapflights users on 12/11. 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.
mié. 12/3112:39 pmBOS - HPN
1 stop20h 13mCape Air
sáb. 1/35:16 pmHPN - BOS
1 stop22h 02mCape Air
Deal found 12/11$375
This Cape Air deal was found by Cheapflights users on 12/10. 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.
jue. 12/258:48 amBOS - HPN
1 stop7h 58mCape Air
lun. 12/295:16 pmHPN - BOS
1 stop18h 42mCape Air
Deal found 12/10$395
This Cape Air deal was found by Cheapflights users on 12/10. 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.
mié. 12/242:24 pmBOS - HPN
1 stop18h 28mCape Air
sáb. 12/279:23 amHPN - BOS
1 stop5h 55mCape Air
Deal found 12/10$415
This Cape Air deal was found by Cheapflights users on 12/10. 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.
sáb. 12/208:48 amBOS - HPN
1 stop7h 58mCape Air
sáb. 12/275:16 pmHPN - BOS
1 stop23h 54mCape Air
Deal found 12/10$435
This Cape Air deal was found by Cheapflights users on 12/11. 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.
lun. 12/228:48 amBOS - HPN
1 stop24h 04mCape Air
lun. 12/295:16 pmHPN - BOS
1 stop22h 02mCape Air
Deal found 12/11$445
This Cape Air deal was found by Cheapflights users on 12/10. 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.
dom. 12/212:24 pmBOS - HPN
1 stop26h 22mCape Air
dom. 12/289:23 amHPN - BOS
1 stop26h 35mCape Air
Deal found 12/10$455
This JetBlue deal was found by Cheapflights users on 12/10. 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.
mar. 12/166:00 amBOS - HPN
1 stop7h 35mJetBlue
jue. 12/188:40 amHPN - BOS
1 stop9h 27mJetBlue
Deal found 12/10$463
This Cape Air deal was found by Cheapflights users on 12/11. 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.
sáb. 12/132:24 pmBOS - HPN
1 stop18h 28mCape Air
lun. 12/159:23 amHPN - BOS
1 stop5h 55mCape Air
Deal found 12/11$465
This Cape Air deal was found by Cheapflights users on 12/11. 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.
lun. 12/158:48 amBOS - HPN
1 stop7h 58mCape Air
lun. 12/295:16 pmHPN - BOS
1 stop22h 02mCape Air
Deal found 12/11$475
This JetBlue deal was found by Cheapflights users on 12/11. 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.
vie. 12/122:59 pmBOS - HPN
1 stop8h 02mJetBlue
dom. 12/141:00 pmHPN - BOS
1 stop7h 14mJetBlue
Deal found 12/11$505
This Cape Air deal was found by Cheapflights users on 12/10. 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.
vie. 12/122:24 pmBOS - HPN
1 stop26h 22mCape Air
dom. 12/149:23 amHPN - BOS
1 stop7h 47mCape Air
Deal found 12/10$525
This KAYAK deal was found by Cheapflights users on 12/11. 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.
mar. 12/166:00 amBOS - HPN
1 stop7h 35mJetBlue
mar. 12/167:00 pmHPN - BOS
1 stop15h 09mJetBlue
Deal found 12/11$528

Find flight deals from Boston to Westchester County

Keep the following information in mind while searching for Boston to Westchester County flight deals. Data was last updated diciembre 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$305
(Expedia)

One-way from

$185
(Cape Air)

Popular in

February

Cheapest in

November

Average price

$187
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.
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From Boston Logan Intl to Westchester County
Search Deals
One-way flight from Boston Logan Intl to Westchester County
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($16 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 Boston 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 diciembre 12, 2025.
Use the filters below to find and compare flights from Boston to Westchester County that are best for you.

Fly from

Boston

Fly to

Westchester County

Route

Depart

Return

Price

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

lun. 1/19

8:04 pm-9:27 am

1 stop13h 23m

White Plains Westchester County

mié. 1/21

2:59 pm-10:10 pm

1 stop7h 11m

$305

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

sáb. 1/31

11:40 am-6:31 pm

1 stop6h 51m

White Plains Westchester County

mar. 2/3

1:00 pm-11:48 pm

1 stop10h 48m

$323

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

vie. 3/6

12:39 pm-8:52 am

1 stop20h 13m

White Plains Westchester County

lun. 3/9

5:16 pm-3:18 pm

1 stop22h 02m

$375

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

jue. 2/12

5:40 pm-8:52 am

1 stop15h 12m

White Plains Westchester County

lun. 2/16

9:23 am-5:10 pm

1 stop7h 47m

$375

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

lun. 3/9

8:48 am-4:46 pm

1 stop7h 58m

White Plains Westchester County

mié. 3/11

9:23 am-11:58 am

1 stop26h 35m

$375

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

mié. 12/31

12:39 pm-8:52 am

1 stop20h 13m

White Plains Westchester County

sáb. 1/3

5:16 pm-3:18 pm

1 stop22h 02m

$375

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

jue. 12/25

8:48 am-4:46 pm

1 stop7h 58m

White Plains Westchester County

lun. 12/29

5:16 pm-11:58 am

1 stop18h 42m

$395

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

vie. 1/9

8:48 am-8:52 am

1 stop24h 04m

White Plains Westchester County

vie. 1/16

9:23 am-8:10 am

1 stop22h 47m

$395

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

jue. 1/8

12:39 pm-4:46 pm

1 stop4h 07m

White Plains Westchester County

jue. 1/15

9:23 am-8:10 am

1 stop22h 47m

$395

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

sáb. 1/17

5:40 pm-8:52 am

1 stop15h 12m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 17 results
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Best time to book a flight from Boston to Westchester County

Have a flexible travel schedule? Discover the best time to fly to Westchester County from Boston 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 Boston to Westchester County
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Boston 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 airport do you fly from for flights from Boston to Westchester County?

    If you book a flight to Westchester County from Boston, you will be flying from Logan Intl, which is the city’s only airport. Boston Logan Intl (BOS) is located 2.6 mi from the center of Boston.

  • How long is the flight from Boston to Westchester County?

    Departing from Boston to Westchester County will take you 13h 23m. There are 165 mi between Boston and Westchester County. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Boston 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 Boston to Westchester County

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