HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Westchester County

$118+ Cheap flights from Boston (BOS) to Westchester County

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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HPN
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Boston to Westchester County 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 Boston to Westchester County

Keep the following information in mind while searching for Boston to Westchester County flight deals. Data was last updated October 27, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$273
(JetBlue)

One-way from

$166
(Kiwi.com)

Popular in

February

Cheapest in

December

Average price

$177
Provider with most accurate pricing for Boston Logan Intl-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-New York (NYC) flights.
Search Deals
From Boston Logan Intl to Westchester County
Search Deals
One-way flight from Boston Logan Intl to Westchester County
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($12 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 October 2025
Search Deals

Find flight deals from Boston to Westchester County

Cheapest flights from Boston to Westchester County
Explore the most affordable flight options available from Boston to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2025.

This JetBlue deal was found by Cheapflights users on 10/26. 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.
Mon 11/102:15 pmBOS - HPN
1 stop9h 12mJetBlue
Thu 11/136:30 amHPN - BOS
1 stop6h 47mJetBlue
Deal found 10/26$273
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Sun 11/99:37 amBOS - HPN
1 stop25h 51mMultiple Airlines
Thu 11/138:00 amHPN - BOS
2 stops27h 55mMultiple Airlines
Deal found 10/25$274
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/179:23 amBOS - HPN
2 stops26h 06mMultiple Airlines
Fri 11/2112:10 pmHPN - BOS
1 stop22h 14mMultiple Airlines
Deal found 10/26$277
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/106:00 amBOS - HPN
1 stop14h 45mMultiple Airlines
Thu 11/1312:09 pmHPN - BOS
2 stops20h 19mMultiple Airlines
Deal found 10/26$330
This Expedia deal was found by Cheapflights users on 10/26. 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.
Thu 11/206:00 amBOS - HPN
1 stop13h 40mJetBlue
Sun 11/234:29 pmHPN - BOS
1 stop8h 20mJetBlue
Deal found 10/26$337
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/810:00 amBOS - HPN
2 stops8h 19mAmerican Airlines
Sun 11/96:30 amHPN - BOS
2 stops9h 30mAmerican Airlines
Deal found 10/26$339
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/66:00 amBOS - HPN
1 stop6h 39mMultiple Airlines
Sat 11/88:00 amHPN - BOS
2 stops25h 58mMultiple Airlines
Deal found 10/27$365
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/206:00 amBOS - HPN
1 stop6h 39mMultiple Airlines
Fri 11/2112:10 pmHPN - BOS
1 stop22h 14mMultiple Airlines
Deal found 10/25$377
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/209:02 amBOS - HPN
2 stops11h 28mMultiple Airlines
Sun 11/231:19 pmHPN - BOS
1 stop9h 38mMultiple Airlines
Deal found 10/26$389

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Westchester County 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 October 27, 2025.
Use the filters below to find and compare flights from Boston to Westchester County that are best for you.

Fly from

Boston

Fly to

Westchester County

Route

Depart

Return

Price

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Mon 11/10

2:15 pm-11:27 pm

1 stop9h 12m

White Plains Westchester County

Thu 11/13

6:30 am-1:17 pm

1 stop6h 47m

$273

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Mon 11/17

9:23 am-11:29 am

2 stops26h 06m

White Plains Westchester County

Fri 11/21

12:10 pm-10:24 am

1 stop22h 14m

$277

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Sun 11/9

9:37 am-11:28 am

1 stop25h 51m

White Plains Westchester County

Thu 11/13

1:19 pm-11:53 pm

1 stop10h 34m

$285

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Thu 11/20

6:00 am-7:40 pm

1 stop13h 40m

White Plains Westchester County

Sun 11/23

4:29 pm-12:49 am

1 stop8h 20m

$337

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Sat 11/8

10:00 am-6:19 pm

2 stops8h 19m

White Plains Westchester County

Sun 11/9

6:30 am-4:00 pm

2 stops9h 30m

$339

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Tue 1/6

12:39 pm-4:46 pm

1 stop4h 07m

White Plains Westchester County

Mon 1/12

9:23 am-3:19 pm

1 stop5h 56m

$375

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Thu 11/20

9:02 am-8:30 pm

2 stops11h 28m

White Plains Westchester County

Sun 11/23

1:19 pm-10:57 pm

1 stop9h 38m

$389

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Thu 11/20

6:00 am-12:39 pm

1 stop6h 39m

White Plains Westchester County

Fri 11/21

8:00 am-11:53 pm

2 stops15h 53m

$392

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Sat 12/20

8:48 am-4:46 pm

1 stop7h 58m

White Plains Westchester County

Wed 12/31

9:23 am-11:58 am

1 stop26h 35m

$395

BostonWhite Plains

BOS - HPN

BOSHPN

Boston Logan Intl

Tue 12/2

5:40 pm-4:46 pm

1 stop23h 06m

White Plains Westchester County

Thu 12/4

9:23 am-11:58 am

1 stop26h 35m

$445

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 21 results
1
2
3

Best time to book a flight from Boston to Westchester County

Have a flexible travel schedule? Discover the best time to fly to Westchester County from Boston 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 Boston to Westchester County
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 Boston to Westchester County. 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 from for flights from Boston to Westchester County?

    If you book a flight to Westchester County from Boston, you will be flying from 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 Boston to Westchester County?

    Departing from Boston to Westchester County will take you 8h 19m. There are 165 mi between Boston and Westchester County. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Boston to Westchester County that include hotel bookings?

    Yes. In addition to deals on Boston to Westchester County flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Westchester County?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Westchester County.

  • Can I find deals for business class flights from Boston to Westchester County?

    Yes. Cheapflights offers flight deals from Boston to Westchester County 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

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 Boston to Westchester County

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