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$131+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
Mar 16 — Mar 231
Mon 3/16
Mon 3/23
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 February 14, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Fri 2/2712:08 pm
HPN
-
BOS
1 stop22h 42m
Multiple Airlines
Tue 3/34:22 pm
BOS
-
HPN
2 stops20h 25m
Multiple Airlines
Deal found 2/11$273
This Priceline deal was found by Cheapflights users on 2/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/810:00 am
HPN
-
BOS
1 stop8h 59m
Multiple Airlines
Thu 4/98:48 am
BOS
-
HPN
1 stop7h 58m
Multiple Airlines
Deal found 2/11$310
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 2/269:23 am
HPN
-
BOS
1 stop5h 55m
Multiple Airlines
Mon 3/24:22 pm
BOS
-
HPN
2 stops19h 06m
Multiple Airlines
Deal found 2/10$313
This Mytrip deal was found by Cheapflights users on 2/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/139:23 am
HPN
-
BOS
1 stop5h 55m
Cape Air
Fri 3/2012:39 pm
BOS
-
HPN
1 stop4h 07m
Cape Air
Deal found 2/13$317
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
Mon 3/169:23 am
HPN
-
BOS
1 stop5h 55m
Multiple Airlines
Mon 3/239:45 am
BOS
-
HPN
2 stops25h 43m
Multiple Airlines
Deal found 2/14$320
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 3/55:16 pm
HPN
-
BOS
1 stop14h 54m
Multiple Airlines
Sun 3/812:56 pm
BOS
-
HPN
1 stop22h 32m
Multiple Airlines
Deal found 2/13$326
This Cape Air deal was found by Cheapflights users on 2/10. 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.
Sat 2/145:16 pm
HPN
-
BOS
1 stop22h 02m
Cape Air
Sun 2/155:40 pm
BOS
-
HPN
1 stop15h 12m
Cape Air
Deal found 2/10$330
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Sat 5/3012:00 pm
HPN
-
BOS
1 stop22h 47m
Multiple Airlines
Mon 6/810:12 am
BOS
-
HPN
1 stop7h 17m
Multiple Airlines
Deal found 2/12$331
This Cape Air deal was found by Cheapflights users on 2/12. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:16 pm
HPN
-
BOS
1 stop23h 54m
Cape Air
Sat 2/288:48 am
BOS
-
HPN
1 stop7h 58m
Cape Air
Deal found 2/12$335
This Kiwi.com deal was found by Cheapflights users on 2/13. 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.
Mon 3/239:23 am
HPN
-
BOS
1 stop5h 55m
Multiple Airlines
Tue 3/244:23 pm
BOS
-
HPN
2 stops20h 24m
Multiple Airlines
Deal found 2/13$345

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 February 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$273
(Kiwi.com)

One-way from

$131
(Kiwi.com)

Popular in

February

Cheapest in

November

Average price

$270
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. 4% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 14, 2026.
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 4/8

10:00 am-6:59 pm

1 stop8h 59m

Boston Logan Intl

Thu 4/9

8:48 am-4:46 pm

1 stop7h 58m

$310

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 2/26

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Mon 3/2

4:22 pm-11:28 am

2 stops19h 06m

$313

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 3/13

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Fri 3/20

12:39 pm-4:46 pm

1 stop4h 07m

$317

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 3/16

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Mon 3/23

9:45 am-11:28 am

2 stops25h 43m

$320

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 2/27

12:08 pm-10:50 am

1 stop22h 42m

Boston Logan Intl

Tue 3/3

8:48 am-4:46 pm

1 stop7h 58m

$322

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 3/23

5:16 pm-11:58 am

1 stop18h 42m

Boston Logan Intl

Tue 3/24

2:24 pm-8:52 am

1 stop18h 28m

$330

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 3/12

5:16 pm-3:18 pm

1 stop22h 02m

Boston Logan Intl

Thu 3/19

8:48 am-8:52 am

1 stop24h 04m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 3/12

9:23 am-5:10 pm

1 stop7h 47m

Boston Logan Intl

Wed 3/18

8:48 am-8:52 am

1 stop24h 04m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 2/28

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Wed 3/4

2:24 pm-4:46 pm

1 stop26h 22m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 3/5

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Mon 3/9

2:24 pm-8:52 am

1 stop18h 28m

$335

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/13

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 5h 55m. 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
Medford
Cambridge
Hampton Beach
Watertown
Seekonk
Brockton
Concord
Seabrook
Cranston
Lincoln
Warwick
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
Lowell

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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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