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Westchester County

$130+ 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 9/29. 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
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Cheap 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 August 14, 2025.

Round-trip from

$253
(Priceline)

One-way from

$130
(JetBlue)

Popular in

February

Cheapest in

October

Average price

$186
From Boston Logan Intl to Westchester County
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One-way flight from Boston Logan Intl to Westchester County
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Highest demand for flights based on searches. 13% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 14, 2025.

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 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.
Wed 12/32:00 pmBOS - HPN
1 stop7h 30mJetBlue
Mon 12/81:00 pmHPN - BOS
1 stop7h 15mJetBlue
Deal found 8/13$326
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
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/108:43 amBOS - HPN
1 stop8h 08mCape Air
Thu 9/119:18 amHPN - BOS
1 stop6h 06mCape Air
Deal found 8/14$406
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.
Fri 9/1211:25 amBOS - HPN
1 stop11h 23mJetBlue
Fri 9/199:39 amHPN - BOS
1 stop10h 21mJetBlue
Deal found 8/13$417
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2912:39 pmBOS - HPN
1 stop20h 14mCape Air
Tue 9/29:18 amHPN - BOS
1 stop6h 06mCape Air
Deal found 8/14$435
This Cape Air 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/73:20 pmBOS - HPN
1 stop25h 32mCape Air
Mon 11/109:20 amHPN - BOS
1 stop4h 39mCape Air
Deal found 8/14$436

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 August 14, 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

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

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

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Wed 12/3

2:00 pm-9:30 pm

1 stop7h 30m

White Plains Westchester County

Mon 12/8

1:00 pm-8:15 pm

1 stop7h 15m

$326

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Wed 12/3

8:35 am-4:52 pm

1 stop8h 17m

White Plains Westchester County

Tue 12/9

9:20 am-5:44 pm

1 stop8h 24m

$396

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Fri 12/5

8:35 am-4:52 pm

1 stop8h 17m

White Plains Westchester County

Mon 12/8

9:20 am-1:59 pm

1 stop4h 39m

$396

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Thu 12/4

8:35 am-4:52 pm

1 stop8h 17m

White Plains Westchester County

Tue 12/9

9:20 am-5:44 pm

1 stop8h 24m

$396

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Thu 12/4

6:10 pm-4:52 pm

1 stop22h 42m

White Plains Westchester County

Mon 12/8

5:20 pm-1:59 pm

1 stop20h 39m

$396

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 23 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.

  • 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.

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

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

See prices for flight routes from nearby airports that may be better suited for you.
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