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$100+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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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 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/3. 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 3/1012:08 pm
HPN
-
BOS
2 stops9h 53m
Multiple Airlines
Thu 3/1212:56 pm
BOS
-
HPN
1 stop22h 32m
Multiple Airlines
Deal found 2/3$222
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/99:23 am
HPN
-
BOS
1 stop7h 47m
Multiple Airlines
Tue 2/103:43 pm
BOS
-
HPN
2 stops21h 04m
Multiple Airlines
Deal found 2/3$321
This Cape Air deal was found by Cheapflights users on 2/2. 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 2/39:23 am
HPN
-
BOS
1 stop26h 35m
Cape Air
Wed 2/42:24 pm
BOS
-
HPN
1 stop18h 28m
Cape Air
Deal found 2/2$330
This Expedia deal was found by Cheapflights users on 2/2. 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.
Tue 2/177:00 pm
HPN
-
BOS
1 stop14h 12m
Multiple Airlines
Sat 2/2112:39 pm
BOS
-
HPN
1 stop4h 07m
Multiple Airlines
Deal found 2/2$333
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/25:16 pm
HPN
-
BOS
1 stop18h 42m
Cape Air
Thu 2/512:39 pm
BOS
-
HPN
1 stop4h 07m
Cape Air
Deal found 2/2$334
This Cape Air deal was found by Cheapflights users on 2/3. 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 2/79:23 am
HPN
-
BOS
1 stop5h 55m
Cape Air
Mon 2/92:24 pm
BOS
-
HPN
1 stop26h 22m
Cape Air
Deal found 2/3$335
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Sat 2/79:23 am
HPN
-
BOS
1 stop5h 55m
Multiple Airlines
Mon 2/97:00 am
BOS
-
HPN
2 stops28h 28m
Multiple Airlines
Deal found 2/3$416
This Kiwi.com deal was found by Cheapflights users on 2/3. 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
2 stops13h 05m
Multiple Airlines
Fri 2/272:24 pm
BOS
-
HPN
1 stop18h 28m
Multiple Airlines
Deal found 2/3$425
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/25:16 pm
HPN
-
BOS
1 stop18h 42m
Multiple Airlines
Thu 2/53:43 pm
BOS
-
HPN
2 stops19h 45m
Multiple Airlines
Deal found 2/2$440
This Cape Air deal was found by Cheapflights users on 2/2. 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 7/25:20 pm
HPN
-
BOS
1 stop16h 35m
Cape Air
Sun 7/510:20 am
BOS
-
HPN
1 stop22h 20m
Cape Air
Deal found 2/2$455

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 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$222
(Kiwi.com)

One-way from

$100
(Kiwi.com)

Popular in

January

Cheapest in

November

Average price

$233
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. 2% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 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 4, 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

Tue 3/10

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Thu 3/12

12:56 pm-11:28 am

1 stop22h 32m

$281

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 3/26

9:23 am-11:58 am

1 stop26h 35m

Boston Logan Intl

Fri 3/27

2:24 pm-4:46 pm

1 stop26h 22m

$330

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 2/13

9:23 am-11:58 am

1 stop26h 35m

Boston Logan Intl

Sat 2/14

2:24 pm-4:46 pm

1 stop26h 22m

$330

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 3/9

9:23 am-11:58 am

1 stop26h 35m

Boston Logan Intl

Tue 3/10

2:24 pm-4:46 pm

1 stop26h 22m

$330

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 3/26

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Thu 3/26

5:40 pm-4:46 pm

1 stop23h 06m

$330

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 2/17

7:00 pm-9:12 am

1 stop14h 12m

Boston Logan Intl

Sat 2/21

12:39 pm-4:46 pm

1 stop4h 07m

$333

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 2/20

5:16 pm-3:18 pm

1 stop22h 02m

Boston Logan Intl

Fri 2/27

2:24 pm-4:46 pm

1 stop26h 22m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 3/5

5:16 pm-5:10 pm

1 stop23h 54m

Boston Logan Intl

Mon 3/9

2:24 pm-4:46 pm

1 stop26h 22m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 3/6

9:23 am-11:58 am

1 stop26h 35m

Boston Logan Intl

Sun 3/8

8:48 am-8:52 am

1 stop24h 04m

$335

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sun 3/8

9:23 am-3:18 pm

1 stop5h 55m

Boston Logan Intl

Tue 3/10

2:24 pm-8:52 am

1 stop18h 28m

$335

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 23 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
Medford
Cambridge
Hampton Beach
Watertown
Seekonk
Brockton
Seabrook
Cranston
Lincoln
Warwick
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
Lowell
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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