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$121+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
nov. 25 — dec. 21
tir. 11/25
tir. 12/2
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 oktober 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
lør. 11/88:00 amHPN - BOS
2 stops25h 58mMultiple Airlines
ons. 11/129:00 amBOS - HPN
1 stop27h 39mMultiple Airlines
Deal found 10/24$284
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
fre. 11/78:00 amHPN - BOS
1 stop14h 22mMultiple Airlines
søn. 11/99:37 amBOS - HPN
1 stop25h 51mMultiple Airlines
Deal found 10/25$299
This Expedia deal was found by Cheapflights users on 10/24. 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.
ons. 11/128:00 pmHPN - BOS
1 stop12h 57mJetBlue
tor. 11/132:15 pmBOS - HPN
1 stop9h 12mJetBlue
Deal found 10/24$353
This JetBlue deal was found by Cheapflights users on 10/24. 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.
lør. 11/81:00 pmHPN - BOS
1 stop7h 04mJetBlue
ons. 11/122:15 pmBOS - HPN
1 stop9h 12mJetBlue
Deal found 10/24$374
This Priceline deal was found by Cheapflights users on 10/25. 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.
lør. 11/224:15 pmHPN - BOS
1 stop8h 06mJetBlue
søn. 11/237:40 amBOS - HPN
1 stop12h 09mJetBlue
Deal found 10/25$378
This JetBlue deal was found by Cheapflights users on 10/23. 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.
ons. 11/56:30 amHPN - BOS
1 stop6h 47mJetBlue
ons. 11/122:15 pmBOS - HPN
1 stop9h 12mJetBlue
Deal found 10/23$379
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
man. 11/248:00 amHPN - BOS
1 stop14h 57mMultiple Airlines
tir. 11/256:00 amBOS - HPN
1 stop14h 30mMultiple Airlines
Deal found 10/24$400
This Cape Air deal was found by Cheapflights users on 10/24. 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.
søn. 12/215:16 pmHPN - BOS
1 stop23h 54mCape Air
lør. 12/2712:39 pmBOS - HPN
1 stop4h 07mCape Air
Deal found 10/24$415
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
lør. 11/228:00 amHPN - BOS
2 stops26h 24mMultiple Airlines
søn. 11/2312:39 pmBOS - HPN
1 stop4h 07mMultiple Airlines
Deal found 10/25$416

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 oktober 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$284
(Kiwi.com)

One-way from

$121
(JetBlue)

Popular in

April

Cheapest in

November

Average price

$197
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
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One-way flight from Westchester County to Boston Logan Intl
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Highest demand for flights based on searches. 5% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in October 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 oktober 26, 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

fre. 11/7

8:00 am-10:22 pm

1 stop14h 22m

Boston Logan Intl

søn. 11/9

9:37 am-11:28 am

1 stop25h 51m

$299

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

lør. 11/8

1:00 pm-8:04 pm

1 stop7h 04m

Boston Logan Intl

ons. 11/12

2:15 pm-11:27 pm

1 stop9h 12m

$374

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

ons. 11/19

1:14 pm-10:24 am

1 stop21h 10m

Boston Logan Intl

tor. 11/27

12:39 pm-4:46 pm

1 stop4h 07m

$379

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

ons. 11/5

6:30 am-1:17 pm

1 stop6h 47m

Boston Logan Intl

ons. 11/12

2:15 pm-11:27 pm

1 stop9h 12m

$379

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

man. 11/24

8:00 am-10:57 pm

1 stop14h 57m

Boston Logan Intl

tir. 11/25

6:00 am-8:30 pm

1 stop14h 30m

$400

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

lør. 11/22

8:00 am-10:24 am

2 stops26h 24m

Boston Logan Intl

søn. 11/23

12:39 pm-4:46 pm

1 stop4h 07m

$416

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

ons. 11/5

9:23 am-3:19 pm

1 stop5h 56m

Boston Logan Intl

tor. 11/6

6:00 am-12:39 pm

1 stop6h 39m

$421

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

fre. 11/14

7:00 am-4:10 pm

1 stop9h 10m

Boston Logan Intl

man. 11/17

2:15 pm-11:27 pm

1 stop9h 12m

$446

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

tor. 11/27

5:16 pm-8:18 am

1 stop15h 02m

Boston Logan Intl

man. 12/1

5:40 pm-4:46 pm

1 stop23h 06m

$455

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

tir. 11/11

9:23 am-3:19 pm

1 stop5h 56m

Boston Logan Intl

tir. 11/11

5:40 pm-4:46 pm

1 stop23h 06m

$459

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/23

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 04m. 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
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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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