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$125+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$245
(JetBlue)

One-way from

$125
(JetBlue)

Popular in

April

Cheapest in

October

Average price

$197
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. 12% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 14, 2025.

This JetBlue deal was found by Cheapflights users on 8/14. 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.
Thu 9/117:30 amHPN - BOS
1 stop11h 13mJetBlue
Mon 9/156:00 amBOS - HPN
1 stop16h 16mJetBlue
Deal found 8/14$245
This JetBlue deal was found by Cheapflights users on 8/14. 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.
Thu 9/47:30 amHPN - BOS
1 stop10h 53mJetBlue
Thu 9/112:20 pmBOS - HPN
1 stop7h 56mJetBlue
Deal found 8/14$253
This Expedia deal was found by Cheapflights users on 8/13. 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.
Wed 10/157:30 amHPN - BOS
1 stop9h 47mJetBlue
Sat 10/258:55 amBOS - HPN
1 stop12h 35mJetBlue
Deal found 8/13$280
This JetBlue deal was found by Cheapflights users on 8/14. 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.
Sat 9/139:39 amHPN - BOS
1 stop7h 31mJetBlue
Sat 9/2011:45 amBOS - HPN
1 stop11h 03mJetBlue
Deal found 8/14$286
This Priceline deal was found by Cheapflights users on 8/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/109:00 amHPN - BOS
1 stop9h 23mJetBlue
Wed 9/172:20 pmBOS - HPN
1 stop7h 56mJetBlue
Deal found 8/13$293
This JetBlue deal was found by Cheapflights users on 8/14. 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.
Sat 10/47:30 amHPN - BOS
1 stop9h 44mJetBlue
Tue 10/71:10 pmBOS - HPN
1 stop9h 50mJetBlue
Deal found 8/14$303
This JetBlue deal was found by Cheapflights users on 8/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/277:30 amHPN - BOS
1 stop10h 21mJetBlue
Sat 10/412:45 pmBOS - HPN
1 stop10h 01mJetBlue
Deal found 8/13$310
This JetBlue deal was found by Cheapflights users on 8/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/67:30 amHPN - BOS
1 stop10h 21mJetBlue
Sat 9/132:20 pmBOS - HPN
1 stop7h 56mJetBlue
Deal found 8/13$314
This JetBlue deal was found by Cheapflights users on 8/14. 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.
Fri 10/37:30 amHPN - BOS
1 stop11h 16mJetBlue
Tue 10/71:10 pmBOS - HPN
1 stop9h 50mJetBlue
Deal found 8/14$323
This Priceline deal was found by Cheapflights users on 8/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/117:30 amHPN - BOS
1 stop11h 13mJetBlue
Thu 9/1811:00 amBOS - HPN
1 stop11h 16mJetBlue
Deal found 8/12$328
This Priceline deal was found by Cheapflights users on 8/14. 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.
Tue 10/147:30 amHPN - BOS
1 stop9h 47mJetBlue
Wed 10/159:55 amBOS - HPN
1 stop11h 35mJetBlue
Deal found 8/14$337
This Priceline deal was found by Cheapflights users on 8/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/57:30 amHPN - BOS
1 stop10h 50mJetBlue
Sat 9/62:45 pmBOS - HPN
1 stop8h 21mJetBlue
Deal found 8/13$343

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 August 14, 2025.
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

Thu 9/11

7:30 am-6:43 pm

1 stop11h 13m

Boston Logan Intl

Mon 9/15

6:00 am-10:16 pm

1 stop16h 16m

$245

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 9/4

7:30 am-6:23 pm

1 stop10h 53m

Boston Logan Intl

Thu 9/11

2:20 pm-10:16 pm

1 stop7h 56m

$253

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 9/8

7:30 am-6:46 pm

1 stop11h 16m

Boston Logan Intl

Thu 9/11

2:20 pm-10:16 pm

1 stop7h 56m

$253

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 10/15

7:30 am-5:17 pm

1 stop9h 47m

Boston Logan Intl

Sat 10/25

8:55 am-9:30 pm

1 stop12h 35m

$280

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 9/13

9:39 am-5:10 pm

1 stop7h 31m

Boston Logan Intl

Sat 9/20

11:45 am-10:48 pm

1 stop11h 03m

$286

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 9/16

9:39 am-5:13 pm

1 stop7h 34m

Boston Logan Intl

Thu 9/18

11:00 am-10:16 pm

1 stop11h 16m

$293

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 9/29

7:30 am-6:46 pm

1 stop11h 16m

Boston Logan Intl

Wed 10/1

9:54 am-10:06 pm

1 stop12h 12m

$293

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 9/10

9:00 am-6:23 pm

1 stop9h 23m

Boston Logan Intl

Wed 9/17

2:20 pm-10:16 pm

1 stop7h 56m

$293

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 10/4

7:30 am-5:14 pm

1 stop9h 44m

Boston Logan Intl

Tue 10/7

1:10 pm-11:00 pm

1 stop9h 50m

$303

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 10/4

7:30 am-5:14 pm

1 stop9h 44m

Boston Logan Intl

Mon 10/6

1:10 pm-11:00 pm

1 stop9h 50m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

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.

  • 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.

  • What is the cheapest month to book a flight from Westchester County to Boston?

    Currently, January is the cheapest month in which you can book a flight from Westchester County to Boston (average of $218). Flying from Westchester County to Boston in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Watertown
Hampton Beach
Waltham
Seabrook
Lowell
Lincoln
Smithfield
Cranston
Chestnut Hill
Warwick
Peabody
Quincy
York Beach
Chelsea
Swansea
Saugus
Burlington
Braintree

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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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