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$126+ Cheap flights from Westchester County to Boston (BOS)

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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Find flight deals from Westchester County to Boston

Cheapest flights from Westchester County to Boston
Explore the most affordable flight options available from Westchester County to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Fri 12/59:23 amHPN - BOS
1 stop5h 56mMultiple Airlines
Sun 12/710:22 amBOS - HPN
1 stop25h 06mMultiple Airlines
Deal found 11/12$310
This JetBlue deal was found by Cheapflights users on 11/12. 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 12/169:15 amHPN - BOS
1 stop6h 35mJetBlue
Wed 12/172:00 pmBOS - HPN
1 stop8h 00mJetBlue
Deal found 11/12$325
This JetBlue deal was found by Cheapflights users on 11/12. 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.
Mon 12/157:30 amHPN - BOS
1 stop8h 00mJetBlue
Tue 12/168:00 amBOS - HPN
1 stop11h 30mJetBlue
Deal found 11/12$326
This JetBlue deal was found by Cheapflights users on 11/11. 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.
Tue 12/97:00 amHPN - BOS
1 stop11h 10mJetBlue
Fri 12/122:59 pmBOS - HPN
1 stop8h 02mJetBlue
Deal found 11/11$332
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/238:00 amHPN - BOS
2 stops27h 55mMultiple Airlines
Tue 12/26:00 amBOS - HPN
1 stop14h 30mMultiple Airlines
Deal found 11/11$341
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/139:23 amHPN - BOS
1 stop5h 56mMultiple Airlines
Sun 12/1410:22 amBOS - HPN
1 stop25h 06mMultiple Airlines
Deal found 11/11$344
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/111:19 pmHPN - BOS
2 stops20h 38mMultiple Airlines
Thu 12/1810:47 amBOS - HPN
1 stop24h 41mMultiple Airlines
Deal found 11/13$358
This Expedia deal was found by Cheapflights users on 11/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/101:00 pmHPN - BOS
1 stop7h 14mJetBlue
Wed 12/176:00 amBOS - HPN
1 stop7h 35mJetBlue
Deal found 11/12$359
This Flightnetwork deal was found by Cheapflights users on 11/10. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/269:23 amHPN - BOS
1 stop7h 47mCape Air
Fri 1/28:48 amBOS - HPN
1 stop7h 58mCape Air
Deal found 11/10$361
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/109:23 amHPN - BOS
1 stop5h 56mMultiple Airlines
Wed 12/178:11 pmBOS - HPN
2 stops15h 18mMultiple Airlines
Deal found 11/12$363
This JetBlue deal was found by Cheapflights users on 11/11. 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.
Thu 12/112:30 pmHPN - BOS
1 stop6h 32mJetBlue
Fri 12/1212:39 pmBOS - HPN
1 stop10h 22mJetBlue
Deal found 11/11$368

Cheap flight deals from Westchester County to Boston

Keep the following information in mind while searching for Westchester County to Boston flight deals. Data was last updated November 13, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$283
(Expedia)

One-way from

$126
(Priceline)

Popular in

April

Cheapest in

December

Average price

$226
Provider with most accurate pricing for New York (NYC)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Boston Logan Intl flights.
Search Deals
From Westchester County to Boston Logan Intl
Search Deals
One-way flight from Westchester County to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Boston 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 November 13, 2025.
Use the filters below to find and compare flights from Westchester County to Boston that are best for you.

Fly from

Westchester County

Fly to

Boston

Route

Depart

Return

Price

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 1/10

7:00 am-8:20 pm

1 stop13h 20m

Boston Logan Intl

Mon 1/12

2:15 pm-11:00 pm

1 stop8h 45m

$283

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 1/10

9:23 am-3:19 pm

1 stop5h 56m

Boston Logan Intl

Mon 1/12

11:41 am-11:28 am

2 stops23h 47m

$307

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 1/9

7:00 am-3:04 pm

1 stop8h 04m

Boston Logan Intl

Mon 1/12

2:15 pm-11:00 pm

1 stop8h 45m

$308

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 12/16

9:15 am-3:50 pm

1 stop6h 35m

Boston Logan Intl

Wed 12/17

2:00 pm-10:00 pm

1 stop8h 00m

$325

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 12/9

7:00 am-6:10 pm

1 stop11h 10m

Boston Logan Intl

Fri 12/12

2:59 pm-11:01 pm

1 stop8h 02m

$332

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 12/5

9:23 am-3:19 pm

1 stop5h 56m

Boston Logan Intl

Sun 12/7

12:57 pm-11:28 am

2 stops22h 31m

$339

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 12/11

1:19 pm-9:57 am

2 stops20h 38m

Boston Logan Intl

Thu 12/18

10:47 am-11:28 am

1 stop24h 41m

$358

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 12/26

9:23 am-5:10 pm

1 stop7h 47m

Boston Logan Intl

Fri 1/2

8:48 am-4:46 pm

1 stop7h 58m

$361

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 12/10

9:23 am-3:19 pm

1 stop5h 56m

Boston Logan Intl

Wed 12/17

8:11 pm-11:29 am

2 stops15h 18m

$363

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 12/11

2:30 pm-9:02 pm

1 stop6h 32m

Boston Logan Intl

Fri 12/12

12:39 pm-11:01 pm

1 stop10h 22m

$368

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 21 results
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Best time to book a flight from Westchester County to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Westchester County 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 Westchester County to Boston
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 Westchester County to Boston. 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 into for flights to Boston from Westchester County?

    If you book a flight to Boston from Westchester County, you will be flying to 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 Westchester County to Boston?

    Departing from Westchester County to Boston will take you 13h 20m. Airlines will cover a distance of 165 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Westchester County to Boston 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Peabody
Quincy
York Beach
Warwick
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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Alternative routes for Westchester County to Boston

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