HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Boston

$139+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
feb. 19 — feb. 261
jue. 2/19
jue. 2/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Westchester County to Boston with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 enero 20, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/199:23 am
HPN
-
BOS
1 stop5h 55m
Multiple Airlines
jue. 2/2610:01 am
BOS
-
HPN
1 stop25h 27m
Multiple Airlines
Deal found 1/20$276
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
mié. 3/251:27 pm
HPN
-
BOS
1 stop22h 13m
Multiple Airlines
vie. 3/2712:39 pm
BOS
-
HPN
1 stop4h 07m
Multiple Airlines
Deal found 1/19$288
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
mar. 2/1712:08 pm
HPN
-
BOS
2 stops9h 53m
Multiple Airlines
vie. 2/2012:39 pm
BOS
-
HPN
1 stop20h 13m
Multiple Airlines
Deal found 1/18$296
This SmartFares deal was found by Cheapflights users on 1/18. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 1/249:23 am
HPN
-
BOS
1 stop5h 55m
Cape Air
dom. 1/2512:39 pm
BOS
-
HPN
1 stop4h 07m
Cape Air
Deal found 1/18$302
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
lun. 2/212:08 pm
HPN
-
BOS
2 stops26h 30m
Multiple Airlines
vie. 2/68:48 am
BOS
-
HPN
1 stop7h 58m
Multiple Airlines
Deal found 1/18$308
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/265:16 pm
HPN
-
BOS
1 stop14h 54m
Multiple Airlines
lun. 3/24:22 pm
BOS
-
HPN
2 stops19h 06m
Multiple Airlines
Deal found 1/20$312
This Flightnetwork deal was found by Cheapflights users on 1/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/25:16 pm
HPN
-
BOS
1 stop18h 42m
Cape Air
mar. 2/32:24 pm
BOS
-
HPN
1 stop26h 22m
Cape Air
Deal found 1/20$315
This Mytrip deal was found by Cheapflights users on 1/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 1/185:16 pm
HPN
-
BOS
1 stop14h 54m
Cape Air
dom. 2/225:40 pm
BOS
-
HPN
1 stop15h 12m
Cape Air
Deal found 1/17$318
This Booking.com deal was found by Cheapflights users on 1/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/145:16 pm
HPN
-
BOS
1 stop14h 54m
Cape Air
lun. 2/162:24 pm
BOS
-
HPN
1 stop18h 28m
Cape Air
Deal found 1/20$319
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
mar. 2/1012:08 pm
HPN
-
BOS
2 stops11h 11m
Multiple Airlines
jue. 2/1210:01 am
BOS
-
HPN
1 stop25h 27m
Multiple Airlines
Deal found 1/19$320
This Cape Air deal was found by Cheapflights users on 1/20. 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 Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 1/219:23 am
HPN
-
BOS
1 stop5h 55m
Cape Air
mié. 1/215:40 pm
BOS
-
HPN
1 stop15h 12m
Cape Air
Deal found 1/20$330

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 enero 20, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$276
(Kiwi.com)

One-way from

$139
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$257
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. 3% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 enero 20, 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

jue. 2/19

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

jue. 2/26

10:01 am-11:28 am

1 stop25h 27m

$276

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

mié. 3/25

1:27 pm-11:40 am

1 stop22h 13m

Boston Logan Intl

vie. 3/27

12:39 pm-4:46 pm

1 stop4h 07m

$288

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

mar. 2/17

12:08 pm-10:01 pm

2 stops9h 53m

Boston Logan Intl

vie. 2/20

12:39 pm-8:52 am

1 stop20h 13m

$296

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

vie. 2/27

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

lun. 3/2

4:22 pm-11:28 am

2 stops19h 06m

$312

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

lun. 2/2

5:16 pm-11:58 am

1 stop18h 42m

Boston Logan Intl

mar. 2/3

2:24 pm-4:46 pm

1 stop26h 22m

$315

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

mié. 2/4

5:16 pm-8:10 am

1 stop14h 54m

Boston Logan Intl

dom. 2/8

6:00 am-11:28 am

2 stops29h 28m

$318

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

mar. 2/10

12:08 pm-11:19 pm

2 stops11h 11m

Boston Logan Intl

jue. 2/12

10:01 am-11:28 am

1 stop25h 27m

$320

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

lun. 2/9

5:16 pm-3:18 pm

1 stop22h 02m

Boston Logan Intl

mar. 2/10

5:40 pm-8:52 am

1 stop15h 12m

$330

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

vie. 2/27

5:16 pm-11:58 am

1 stop18h 42m

Boston Logan Intl

sáb. 2/28

2:24 pm-8:52 am

1 stop18h 28m

$330

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

vie. 2/6

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

vie. 2/6

5:40 pm-4:46 pm

1 stop23h 06m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

Showing 1-10 of 21 results
1
2
3

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 18h 42m. 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
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
Lowell
Chelsea

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Westchester County to Boston

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Boston flights
Newark to Boston flights
LaGuardia to Boston flights
Rochester to Boston flights
Syracuse to Boston flights
Buffalo to Boston flights
Islip to Boston flights
John F Kennedy Intl to West Tisbury flights
John F Kennedy Intl to Nantucket flights
LaGuardia to Nantucket flights
Newark to Nantucket flights
LaGuardia to Hyannis flights
John F Kennedy Intl to Hyannis flights
LaGuardia to West Tisbury flights
Newark to Albany flights
John F Kennedy Intl to Albany flights
Albany to Boston flights
John F Kennedy Intl to Hartford flights
Stewart to Boston flights
White Plains to Nantucket flights
LaGuardia to Albany flights
White Plains to Boston flights
Buffalo to Albany flights
Buffalo to Hartford flights
Newark to Hartford flights
John F Kennedy Intl to Worcester flights
LaGuardia to Hartford flights
Rochester to Hartford flights
LaGuardia to Worcester flights
Ithaca to Boston flights
Saranac Lake to Boston flights
Rutland to Boston flights
White Plains to Albany flights
White Plains to West Tisbury flights
White Plains to Hyannis flights
White Plains to Hartford flights
Islip to Albany flights
Rochester to Nantucket flights
Syracuse to Nantucket flights
Newark to West Tisbury flights
White Plains to New Bedford flights
Elmira to Boston flights
Buffalo to Hyannis flights
Syracuse to Hyannis flights
Binghamton to Boston flights
Syracuse to West Tisbury flights
Plattsburgh to Boston flights
John F Kennedy Intl to Provincetown flights
Newark to Hyannis flights
Stewart to Hartford flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights