HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Boston

$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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
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 February 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/9. 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 3/912:08 pm
HPN
-
BOS
2 stops23h 40m
Multiple Airlines
Mon 3/1612:39 pm
BOS
-
HPN
1 stop4h 07m
Multiple Airlines
Deal found 2/9$307
This Priceline deal was found by Cheapflights users on 2/11. 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 4/810:00 am
HPN
-
BOS
1 stop8h 59m
Multiple Airlines
Thu 4/98:48 am
BOS
-
HPN
1 stop7h 58m
Multiple Airlines
Deal found 2/11$310
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 2/269:23 am
HPN
-
BOS
1 stop5h 55m
Multiple Airlines
Mon 3/24:22 pm
BOS
-
HPN
2 stops19h 06m
Multiple Airlines
Deal found 2/10$313
This Gotogate deal was found by Cheapflights users on 2/9. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/239:23 am
HPN
-
BOS
1 stop5h 55m
Cape Air
Mon 2/235:40 pm
BOS
-
HPN
1 stop23h 06m
Cape Air
Deal found 2/9$314
This JetBlue deal was found by Cheapflights users on 2/9. 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 3/102:30 pm
HPN
-
BOS
1 stop9h 29m
JetBlue
Wed 3/111:55 pm
BOS
-
HPN
1 stop8h 50m
JetBlue
Deal found 2/9$326
This Cape Air deal was found by Cheapflights users on 2/10. 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.
Sat 2/145:16 pm
HPN
-
BOS
1 stop22h 02m
Cape Air
Sun 2/155:40 pm
BOS
-
HPN
1 stop15h 12m
Cape Air
Deal found 2/10$330
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:12 pm
HPN
-
BOS
2 stops18h 50m
Delta
Wed 3/117:49 pm
BOS
-
HPN
2 stops16h 04m
Delta
Deal found 2/9$334
This Cape Air deal was found by Cheapflights users on 2/9. 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.
Mon 3/99:23 am
HPN
-
BOS
1 stop5h 55m
Cape Air
Fri 3/1312:39 pm
BOS
-
HPN
1 stop4h 07m
Cape Air
Deal found 2/9$335
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 2/2012:08 pm
HPN
-
BOS
1 stop22h 42m
Multiple Airlines
Sun 3/294:23 pm
BOS
-
HPN
2 stops19h 05m
Multiple Airlines
Deal found 2/8$339
This Cape Air deal was found by Cheapflights users on 2/9. 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 3/265:16 pm
HPN
-
BOS
1 stop23h 54m
Cape Air
Thu 4/22:24 pm
BOS
-
HPN
1 stop18h 28m
Cape Air
Deal found 2/9$365
This Delta deal was found by Cheapflights users on 2/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/44:19 pm
HPN
-
BOS
1 stop8h 44m
Delta
Sat 7/115:45 am
BOS
-
HPN
1 stop28h 07m
Delta
Deal found 2/8$393
This Cape Air deal was found by Cheapflights users on 2/9. 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.
Fri 4/179:23 am
HPN
-
BOS
1 stop7h 47m
Cape Air
Sun 4/198:48 am
BOS
-
HPN
1 stop24h 04m
Cape Air
Deal found 2/9$395

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 February 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$307
(Kiwi.com)

One-way from

$110
(JetBlue)

Popular in

February

Cheapest in

November

Average price

$270
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. 4% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 11, 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

Wed 4/8

10:00 am-6:59 pm

1 stop8h 59m

Boston Logan Intl

Thu 4/9

8:48 am-4:46 pm

1 stop7h 58m

$310

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 2/26

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Mon 3/2

4:22 pm-11:28 am

2 stops19h 06m

$313

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 3/9

5:17 pm-9:00 am

2 stops15h 43m

Boston Logan Intl

Tue 3/17

7:49 pm-11:53 am

2 stops16h 04m

$334

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 3/5

5:16 pm-8:10 am

1 stop14h 54m

Boston Logan Intl

Fri 3/13

5:40 pm-8:52 am

1 stop15h 12m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 3/5

5:16 pm-8:10 am

1 stop14h 54m

Boston Logan Intl

Tue 3/17

8:48 am-4:46 pm

1 stop7h 58m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 3/5

5:16 pm-8:10 am

1 stop14h 54m

Boston Logan Intl

Sun 3/15

8:48 am-4:46 pm

1 stop7h 58m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 3/6

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Mon 3/16

5:40 pm-8:52 am

1 stop15h 12m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 3/5

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Mon 3/9

2:24 pm-8:52 am

1 stop18h 28m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 3/27

9:23 am-5:10 pm

1 stop7h 47m

Boston Logan Intl

Mon 3/30

5:40 pm-8:52 am

1 stop15h 12m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 3/6

5:16 pm-5:10 pm

1 stop23h 54m

Boston Logan Intl

Sun 3/8

5:40 pm-8:52 am

1 stop15h 12m

$335

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

Showing 1-10 of 22 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 14h 54m. 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
Medford
Cambridge
Hampton Beach
Watertown
Seekonk
Brockton
Concord
Seabrook
Cranston
Lincoln
Warwick
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
Lowell

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.
Newark to Boston flights
LaGuardia to Boston flights
John F Kennedy Intl to Boston flights
Buffalo to Boston flights
Rochester to Boston flights
Syracuse to Boston flights
John F Kennedy Intl to Nantucket flights
LaGuardia to Nantucket flights
John F Kennedy Intl to West Tisbury flights
Newark to Nantucket flights
Islip to Boston flights
White Plains to Boston flights
John F Kennedy Intl to Hyannis flights
LaGuardia to West Tisbury flights
John F Kennedy Intl to Albany flights
White Plains to Nantucket flights
Newark to Albany flights
LaGuardia to Hyannis flights
Stewart to Boston flights
John F Kennedy Intl to Hartford flights
LaGuardia to Albany flights
LaGuardia to Worcester flights
White Plains to West Tisbury flights
Newark to Hartford flights
Albany to Boston flights
White Plains to Hyannis flights
John F Kennedy Intl to Worcester flights
LaGuardia to Hartford flights
Rutland to Boston flights
Buffalo to Hartford flights
Rochester to Hartford flights
Buffalo to Albany flights
Stewart to Albany flights
White Plains to Hartford flights
Ithaca to Boston flights
Rochester to Nantucket flights
Newark to West Tisbury flights
Islip to Albany flights
Saranac Lake to Boston flights
Syracuse to Nantucket flights
White Plains to Albany flights
White Plains to New Bedford flights
Elmira to Boston flights
Islip to West Tisbury flights
Buffalo to Hyannis flights
Buffalo to Worcester flights
Buffalo to Nantucket flights
Syracuse to West Tisbury flights
Rochester to West Tisbury flights
Newark to Provincetown 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.