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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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
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 November 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/31:14 pmHPN - BOS
2 stops34h 42mMultiple Airlines
Sun 12/710:22 amBOS - HPN
1 stop25h 06mMultiple Airlines
Deal found 11/18$289
This JetBlue deal was found by Cheapflights users on 11/20. 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 12/51:00 pmHPN - BOS
1 stop10h 11mJetBlue
Tue 12/96:05 amBOS - HPN
1 stop8h 09mJetBlue
Deal found 11/20$365
This Priceline deal was found by Cheapflights users on 11/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/121:00 pmHPN - BOS
1 stop10h 11mJetBlue
Sat 12/133:00 pmBOS - HPN
1 stop8h 01mJetBlue
Deal found 11/17$369
This JetBlue deal was found by Cheapflights users on 11/19. 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 12/41:00 pmHPN - BOS
1 stop10h 11mJetBlue
Mon 12/86:05 amBOS - HPN
1 stop8h 09mJetBlue
Deal found 11/19$375
This FlightHub deal was found by Cheapflights users on 11/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/169:23 amHPN - BOS
1 stop7h 47mCape Air
Tue 12/232:24 pmBOS - HPN
1 stop18h 28mCape Air
Deal found 11/19$390
This Expedia deal was found by Cheapflights users on 11/18. 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 12/37:30 amHPN - BOS
1 stop12h 01mJetBlue
Sun 12/76:05 amBOS - HPN
1 stop8h 09mJetBlue
Deal found 11/18$399
This Kiwi.com deal was found by Cheapflights users on 11/17. 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.
Mon 12/158:00 amHPN - BOS
2 stops39h 56mMultiple Airlines
Mon 12/228:48 amBOS - HPN
1 stop7h 58mMultiple Airlines
Deal found 11/17$405
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 12/49:23 amHPN - BOS
1 stop5h 56mMultiple Airlines
Thu 12/48:11 pmBOS - HPN
2 stops15h 17mMultiple Airlines
Deal found 11/19$406
This Kiwi.com deal was found by Cheapflights users on 11/17. 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.
Mon 12/159:23 amHPN - BOS
1 stop5h 55mCape Air
Mon 12/228:48 amBOS - HPN
1 stop7h 58mCape Air
Deal found 11/17$414
This Cape Air deal was found by Cheapflights users on 11/19. 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 stop26h 35mCape Air
Wed 12/248:48 amBOS - HPN
1 stop24h 04mCape Air
Deal found 11/19$415
This Kiwi.com deal was found by Cheapflights users on 11/17. 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.
Fri 12/1212:10 pmHPN - BOS
2 stops21h 51mMultiple Airlines
Sat 12/1312:39 pmBOS - HPN
1 stop4h 07mMultiple Airlines
Deal found 11/17$420

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 November 20, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$289
(Kiwi.com)

One-way from

$110
(Priceline)

Popular in

April

Cheapest in

December

Average price

$226
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.
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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 ($7 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 November 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 November 20, 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

Sat 1/10

2:00 pm-9:17 pm

1 stop7h 17m

Boston Logan Intl

Tue 1/13

6:45 am-4:28 pm

1 stop9h 43m

$309

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 1/5

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Thu 1/8

3:43 pm-11:28 am

2 stops19h 45m

$325

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 3/26

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Tue 3/31

12:39 pm-4:46 pm

1 stop4h 07m

$363

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 1/14

5:16 pm-11:58 am

1 stop18h 42m

Boston Logan Intl

Thu 1/15

2:24 pm-8:52 am

1 stop18h 28m

$363

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 12/5

1:00 pm-11:11 pm

1 stop10h 11m

Boston Logan Intl

Tue 12/9

6:05 am-2:14 pm

1 stop8h 09m

$365

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 2/6

9:23 am-5:10 pm

1 stop7h 47m

Boston Logan Intl

Mon 2/9

12:39 pm-4:46 pm

1 stop4h 07m

$369

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 12/4

1:00 pm-11:11 pm

1 stop10h 11m

Boston Logan Intl

Mon 12/8

6:05 am-2:14 pm

1 stop8h 09m

$375

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 1/10

5:16 pm-8:10 am

1 stop14h 54m

Boston Logan Intl

Tue 1/13

8:48 am-8:52 am

1 stop24h 04m

$375

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 1/7

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Wed 1/7

5:40 pm-4:46 pm

1 stop23h 06m

$375

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 12/16

9:23 am-5:10 pm

1 stop7h 47m

Boston Logan Intl

Tue 12/23

2:24 pm-8:52 am

1 stop18h 28m

$390

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 20 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. 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
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Peabody
Quincy
York Beach
Warwick
Swansea
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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