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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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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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 September 17, 2025.

Round-trip from

$213
(JetBlue)

One-way from

$121
(JetBlue)

Popular in

April

Cheapest in

October

Average price

$197
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. 7% potential increase in price ($19 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 September 2025
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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 September 17, 2025.

This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/109:39 amHPN - BOS
1 stop7h 24mJetBlue
Sun 10/122:19 pmBOS - HPN
1 stop7h 44mJetBlue
Deal found 9/16$213
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/47:30 amHPN - BOS
1 stop9h 44mJetBlue
Tue 10/711:45 amBOS - HPN
1 stop7h 18mJetBlue
Deal found 9/16$273
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/298:25 amHPN - BOS
1 stop6h 52mMultiple Airlines
Thu 10/28:47 amBOS - HPN
1 stop26h 41mMultiple Airlines
Deal found 9/15$297
This JetBlue deal was found by Cheapflights users on 9/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:30 amHPN - BOS
1 stop10h 17mJetBlue
Sun 10/1910:53 amBOS - HPN
1 stop11h 10mJetBlue
Deal found 9/14$303
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/309:00 amHPN - BOS
1 stop9h 23mJetBlue
Sat 10/42:45 pmBOS - HPN
1 stop8h 44mJetBlue
Deal found 9/15$308
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/31:00 pmHPN - BOS
1 stop9h 30mJetBlue
Tue 10/711:45 amBOS - HPN
1 stop7h 18mJetBlue
Deal found 9/16$313
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/112:00 pmHPN - BOS
1 stop8h 56mMultiple Airlines
Sun 11/99:37 amBOS - HPN
1 stop25h 51mMultiple Airlines
Deal found 9/15$315
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/31:00 pmHPN - BOS
1 stop9h 30mJetBlue
Sat 10/42:45 pmBOS - HPN
1 stop8h 44mJetBlue
Deal found 9/16$323
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:25 amHPN - BOS
1 stop12h 31mMultiple Airlines
Mon 10/209:51 pmBOS - HPN
1 stop22h 39mMultiple Airlines
Deal found 9/15$334
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/131:19 pmHPN - BOS
1 stop19h 08mMultiple Airlines
Sun 11/168:40 amBOS - HPN
1 stop26h 48mMultiple Airlines
Deal found 9/17$338
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/227:30 amHPN - BOS
1 stop10h 17mJetBlue
Thu 10/231:25 pmBOS - HPN
1 stop9h 38mJetBlue
Deal found 9/16$343

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 September 17, 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

Fri 10/10

9:39 am-5:03 pm

1 stop7h 24m

Boston Logan Intl

Sun 10/12

2:19 pm-10:03 pm

1 stop7h 44m

$213

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 10/4

7:30 am-5:14 pm

1 stop9h 44m

Boston Logan Intl

Tue 10/7

11:45 am-7:03 pm

1 stop7h 18m

$273

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 10/16

7:30 am-5:47 pm

1 stop10h 17m

Boston Logan Intl

Sun 10/19

10:53 am-10:03 pm

1 stop11h 10m

$303

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 9/30

9:00 am-6:23 pm

1 stop9h 23m

Boston Logan Intl

Sat 10/4

2:45 pm-11:29 pm

1 stop8h 44m

$308

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 11/1

12:00 pm-8:56 pm

1 stop8h 56m

Boston Logan Intl

Sun 11/9

10:43 am-11:28 am

2 stops24h 45m

$313

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 10/3

1:00 pm-10:30 pm

1 stop9h 30m

Boston Logan Intl

Tue 10/7

11:45 am-7:03 pm

1 stop7h 18m

$313

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 10/3

1:00 pm-10:30 pm

1 stop9h 30m

Boston Logan Intl

Sat 10/4

2:45 pm-11:29 pm

1 stop8h 44m

$323

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 10/17

8:25 am-8:56 pm

1 stop12h 31m

Boston Logan Intl

Mon 10/20

9:51 pm-8:30 pm

1 stop22h 39m

$334

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 11/13

1:19 pm-8:27 am

1 stop19h 08m

Boston Logan Intl

Sun 11/16

8:40 am-11:28 am

1 stop26h 48m

$338

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 10/17

8:25 am-8:56 pm

1 stop12h 31m

Boston Logan Intl

Sun 10/26

8:12 am-11:28 am

1 stop27h 16m

$344

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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 7h 24m. 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.

  • What is the cheapest month to book a flight from Westchester County to Boston?

    Currently, January is the cheapest month in which you can book a flight from Westchester County to Boston (average of $218). Flying from Westchester County to Boston in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Chelsea
Warwick
Peabody
Quincy
York Beach
Swansea
Old Orchard Beach
Brockton
Waltham

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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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