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$119+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
Feb 13 — Feb 201
Fri 2/13
Fri 2/20
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 January 14, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$295
(Kiwi.com)

One-way from

$119
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$237
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. 4% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 14, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/12. 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.
Mon 1/268:00 am
HPN
-
BOS
2 stops30h 38m
Multiple Airlines
Wed 1/286:39 pm
BOS
-
HPN
1 stop18h 01m
Multiple Airlines
Deal found 1/12$295
This Kiwi.com deal was found by Cheapflights users on 1/12. 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.
Fri 2/69:23 am
HPN
-
BOS
1 stop5h 55m
Multiple Airlines
Sat 2/73:43 pm
BOS
-
HPN
2 stops19h 45m
Multiple Airlines
Deal found 1/12$296
This Expedia deal was found by Cheapflights users on 1/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/67:00 am
HPN
-
BOS
1 stop9h 04m
Multiple Airlines
Sat 2/148:48 am
BOS
-
HPN
1 stop7h 58m
Multiple Airlines
Deal found 1/13$302
This Kiwi.com deal was found by Cheapflights users on 1/13. 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.
Tue 1/2712:08 pm
HPN
-
BOS
2 stops26h 30m
Multiple Airlines
Fri 1/305:40 pm
BOS
-
HPN
1 stop15h 12m
Multiple Airlines
Deal found 1/13$310
This Kiwi.com deal was found by Cheapflights users on 1/13. 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.
Wed 1/289:23 am
HPN
-
BOS
1 stop5h 55m
Multiple Airlines
Sun 2/16:00 am
BOS
-
HPN
2 stops29h 28m
Multiple Airlines
Deal found 1/13$315
This Expedia deal was found by Cheapflights users on 1/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/29:23 am
HPN
-
BOS
1 stop7h 47m
Multiple Airlines
Tue 2/37:45 pm
BOS
-
HPN
1 stop13h 42m
Multiple Airlines
Deal found 1/12$329
This Cape Air deal was found by Cheapflights users on 1/13. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/225:16 pm
HPN
-
BOS
1 stop22h 02m
Cape Air
Fri 1/235:40 pm
BOS
-
HPN
1 stop23h 06m
Cape Air
Deal found 1/13$330
This Cape Air deal was found by Cheapflights users on 1/12. 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.
Tue 1/275:16 pm
HPN
-
BOS
1 stop18h 42m
Cape Air
Sat 1/312:24 pm
BOS
-
HPN
1 stop18h 28m
Cape Air
Deal found 1/12$335
This Kiwi.com deal was found by Cheapflights users on 1/12. 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.
Tue 1/205:16 pm
HPN
-
BOS
1 stop14h 54m
Multiple Airlines
Wed 1/213:43 pm
BOS
-
HPN
2 stops19h 45m
Multiple Airlines
Deal found 1/12$341

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 January 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

Mon 1/26

8:00 am-2:38 pm

2 stops30h 38m

Boston Logan Intl

Wed 1/28

6:39 pm-12:40 pm

1 stop18h 01m

$295

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 2/6

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Sat 2/7

3:43 pm-11:28 am

2 stops19h 45m

$296

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 2/4

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Thu 2/5

3:43 pm-11:28 am

2 stops19h 45m

$313

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 2/6

9:23 am-11:58 am

1 stop26h 35m

Boston Logan Intl

Sat 2/7

2:24 pm-8:52 am

1 stop18h 28m

$330

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 2/4

9:23 am-11:58 am

1 stop26h 35m

Boston Logan Intl

Thu 2/5

2:24 pm-4:46 pm

1 stop26h 22m

$330

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 1/27

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Fri 1/30

12:39 pm-8:52 am

1 stop20h 13m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 2/9

9:23 am-5:10 pm

1 stop7h 47m

Boston Logan Intl

Mon 2/16

12:39 pm-4:46 pm

1 stop4h 07m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 2/10

5:16 pm-11:58 am

1 stop18h 42m

Boston Logan Intl

Tue 2/17

12:39 pm-4:46 pm

1 stop4h 07m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 2/16

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Thu 2/19

12:39 pm-4:46 pm

1 stop4h 07m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 2/5

5:16 pm-8:10 am

1 stop14h 54m

Boston Logan Intl

Mon 2/9

8:48 am-4:46 pm

1 stop7h 58m

$335

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/13

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 26h 35m. 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
Seekonk
Brockton
Warwick
Seabrook
Cranston
Lincoln
Lowell
Smithfield
Peabody
Quincy
York Beach
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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