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$130+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Tue 12/1612:09 pmHPN - BOS
2 stops21h 52mMultiple Airlines
Thu 12/1810:47 amBOS - HPN
1 stop24h 41mMultiple Airlines
Deal found 12/9$362
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.
Tue 12/309:23 amHPN - BOS
1 stop26h 35mCape Air
Sat 1/32:24 pmBOS - HPN
1 stop18h 28mCape Air
Deal found 12/11$375
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.
Tue 12/169:15 amHPN - BOS
1 stop9h 29mJetBlue
Wed 12/1710:05 amBOS - HPN
1 stop8h 51mJetBlue
Deal found 12/11$383
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.
Thu 12/255:16 pmHPN - BOS
1 stop18h 42mCape Air
Mon 12/2912:39 pmBOS - HPN
1 stop20h 13mCape Air
Deal found 12/10$415
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Tue 12/169:23 amHPN - BOS
1 stop26h 35mCape Air
Thu 12/188:48 amBOS - HPN
1 stop24h 04mCape Air
Deal found 12/9$416
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/159:23 amHPN - BOS
1 stop5h 55mMultiple Airlines
Tue 12/1610:56 amBOS - HPN
2 stops25h 38mMultiple Airlines
Deal found 12/10$420
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/179:23 amHPN - BOS
1 stop7h 47mMultiple Airlines
Thu 12/1810:47 amBOS - HPN
1 stop24h 41mMultiple Airlines
Deal found 12/11$423
This Kiwi.com 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 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 55mMultiple Airlines
Sun 12/1410:22 amBOS - HPN
1 stop25h 06mMultiple Airlines
Deal found 12/10$434
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.
Fri 12/269:23 amHPN - BOS
1 stop26h 35mCape Air
Tue 12/305:40 pmBOS - HPN
1 stop15h 12mCape Air
Deal found 12/11$435
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:00 pmHPN - BOS
1 stop12h 57mJetBlue
Wed 12/178:00 amBOS - HPN
1 stop10h 56mJetBlue
Deal found 12/11$443
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.
Sat 12/139:10 amHPN - BOS
1 stop9h 38mJetBlue
Sun 12/1410:05 amBOS - HPN
1 stop8h 51mJetBlue
Deal found 12/11$458
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/149:23 amHPN - BOS
1 stop22h 47mMultiple Airlines
Tue 12/168:11 pmBOS - HPN
2 stops16h 23mMultiple Airlines
Deal found 12/10$465

Find 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 December 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$318
(Kiwi.com)

One-way from

$130
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$223
Provider with most accurate pricing for New York (NYC)-Boston Logan Intl flight deals.
Search Deals
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 ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in December 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 December 12, 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

Wed 2/18

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Sun 2/22

10:01 am-11:28 am

1 stop25h 27m

$318

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 1/15

9:23 am-11:58 am

1 stop26h 35m

Boston Logan Intl

Fri 1/16

2:24 pm-4:46 pm

1 stop26h 22m

$369

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 1/20

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Tue 1/20

5:40 pm-4:46 pm

1 stop23h 06m

$369

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 1/20

5:16 pm-8:10 am

1 stop14h 54m

Boston Logan Intl

Thu 1/22

12:39 pm-8:52 am

1 stop20h 13m

$375

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 1/30

9:23 am-5:10 pm

1 stop7h 47m

Boston Logan Intl

Tue 2/3

8:48 am-4:46 pm

1 stop7h 58m

$375

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 1/14

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Sat 1/17

8:48 am-8:52 am

1 stop24h 04m

$375

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 12/30

9:23 am-11:58 am

1 stop26h 35m

Boston Logan Intl

Sat 1/3

2:24 pm-8:52 am

1 stop18h 28m

$375

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 1/23

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Fri 1/23

5:40 pm-4:46 pm

1 stop23h 06m

$379

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sun 1/11

9:23 am-8:10 am

1 stop22h 47m

Boston Logan Intl

Fri 1/16

2:24 pm-4:46 pm

1 stop26h 22m

$385

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 1/7

1:17 pm-11:19 pm

2 stops34h 02m

$130

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 19 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 26h 35m. 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
Cranston
Lincoln
Lowell
Smithfield
Peabody
Brockton
Quincy
York Beach
Warwick
Londonderry
Swansea
Old Orchard Beach
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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