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$110+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 18, 2025.

This Expedia deal was found by Cheapflights users on 12/16. 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 12/318:40 amHPN - BOS
1 stop9h 27mMultiple Airlines
Sun 1/48:48 amBOS - HPN
1 stop7h 58mMultiple Airlines
Deal found 12/16$392
This Cape Air deal was found by Cheapflights users on 12/15. 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 stop5h 55mCape Air
Sat 1/312:39 pmBOS - HPN
1 stop20h 13mCape Air
Deal found 12/15$395
This Cape Air deal was found by Cheapflights users on 12/15. 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 stop5h 55mCape Air
Sun 1/42:24 pmBOS - HPN
1 stop26h 22mCape Air
Deal found 12/15$405
This Cape Air deal was found by Cheapflights users on 12/15. 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.
Mon 12/229:23 amHPN - BOS
1 stop26h 35mCape Air
Tue 12/232:24 pmBOS - HPN
1 stop26h 22mCape Air
Deal found 12/15$429
This Cape Air deal was found by Cheapflights users on 12/16. 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.
Wed 12/319:23 amHPN - BOS
1 stop5h 55mCape Air
Sun 1/48:48 amBOS - HPN
1 stop24h 04mCape Air
Deal found 12/16$435
This Cape Air deal was found by Cheapflights users on 12/17. 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 12/265:16 pmHPN - BOS
1 stop18h 42mCape Air
Sat 12/272:24 pmBOS - HPN
1 stop18h 28mCape Air
Deal found 12/17$449
This Cape Air deal was found by Cheapflights users on 12/16. 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 12/189:23 amHPN - BOS
1 stop26h 35mCape Air
Fri 12/192:24 pmBOS - HPN
1 stop26h 22mCape Air
Deal found 12/16$489
This Cape Air deal was found by Cheapflights users on 12/17. 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.
Wed 12/179:23 amHPN - BOS
1 stop7h 47mCape Air
Thu 12/188:48 amBOS - HPN
1 stop24h 04mCape Air
Deal found 12/17$505
This Mytrip deal was found by Cheapflights users on 12/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/179:23 amHPN - BOS
1 stop5h 55mCape Air
Wed 12/175:40 pmBOS - HPN
1 stop15h 12mCape Air
Deal found 12/16$506
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/1812:09 pmHPN - BOS
2 stops21h 52mMultiple Airlines
Sun 12/2111:36 amBOS - HPN
1 stop23h 52mMultiple Airlines
Deal found 12/16$545

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 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$249
(Kiwi.com)

One-way from

$110
(JetBlue)

Popular in

April

Cheapest in

November

Average price

$225
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.
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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).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 18, 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 1/14

1:17 pm-2:38 pm

2 stops25h 21m

Boston Logan Intl

Wed 1/21

6:39 pm-12:40 pm

1 stop18h 01m

$249

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 1/14

7:30 pm-8:58 am

1 stop13h 28m

Boston Logan Intl

Wed 1/21

8:04 pm-9:27 am

1 stop13h 23m

$285

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 1/20

8:15 am-7:19 pm

1 stop11h 04m

Boston Logan Intl

Thu 1/22

6:38 am-5:42 pm

1 stop11h 04m

$328

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 1/16

7:30 pm-8:58 am

1 stop13h 28m

Boston Logan Intl

Fri 1/23

8:04 pm-9:27 am

1 stop13h 23m

$330

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 2/2

9:23 am-5:10 pm

1 stop7h 47m

Boston Logan Intl

Mon 2/9

8:48 am-4:46 pm

1 stop7h 58m

$375

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 1/31

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Sat 2/7

12:39 pm-4:46 pm

1 stop4h 07m

$375

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 1/22

9:23 am-5:10 pm

1 stop7h 47m

Boston Logan Intl

Sun 1/25

8:48 am-4:46 pm

1 stop7h 58m

$375

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 1/14

5:16 pm-5:10 pm

1 stop23h 54m

Boston Logan Intl

Sat 1/17

5:40 pm-8:52 am

1 stop15h 12m

$375

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 1/16

9:23 am-8:10 am

1 stop22h 47m

Boston Logan Intl

Fri 1/23

5:27 pm-11:28 am

2 stops42h 01m

$389

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 1/1

9:23 am-8:10 am

1 stop22h 47m

Boston Logan Intl

Mon 1/5

11:55 am-11:29 am

2 stops23h 34m

$392

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 22 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 7h 47m. Airlines will cover a distance of 165 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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
Brockton
Cranston
Lincoln
Lowell
Smithfield
Peabody
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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