Boston

$162+ 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
Jul 6 — Jul 131
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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 July 1, 2025.

Round-trip from

$328
(American Airlines)

One-way from

$162
(JetBlue)

Popular in

April

Cheapest in

October

Average price

$172
From Westchester County to Boston Logan Intl
One-way flight from Westchester County to Boston Logan Intl
Highest demand for flights based on searches. 19% potential increase in price ($46 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($6 potential savings vs. average RT price).
Average for round-trip flights in July 2025

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 July 1, 2025.

This American Airlines deal was found by Cheapflights users on 6/29. 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.
Sun 7/276:37 amHPN - BOS
2 stops7h 30mAmerican Airlines
Sun 8/311:52 amBOS - HPN
2 stops11h 36mAmerican Airlines
Deal found 6/29$328
This JetBlue deal was found by Cheapflights users on 6/30. 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.
Wed 7/307:30 amHPN - BOS
1 stop9h 04mJetBlue
Wed 8/63:14 pmBOS - HPN
1 stop7h 15mJetBlue
Deal found 6/30$338
This Gotogate deal was found by Cheapflights users on 6/30. 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.
Thu 10/95:16 pmHPN - BOS
1 stop24h 02mCape Air
Mon 10/1312:39 pmBOS - HPN
1 stop20h 14mCape Air
Deal found 6/30$435
This JetBlue Airways deal was found by Cheapflights users on 6/30. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/158:30 pmHPN - BOS
1 stop12h 34mMultiple Airlines
Sun 8/175:48 pmBOS - HPN
1 stop15h 05mMultiple Airlines
Deal found 6/30$477

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 July 1, 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

Sun 7/27

6:37 am-2:07 pm

2 stops7h 30m

Boston Logan Intl

Sun 8/3

11:52 am-11:28 pm

2 stops11h 36m

$328

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 7/30

7:30 am-4:34 pm

1 stop9h 04m

Boston Logan Intl

Wed 8/6

3:14 pm-10:29 pm

1 stop7h 15m

$338

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 10/9

5:16 pm-5:18 pm

1 stop24h 02m

Boston Logan Intl

Mon 10/13

12:39 pm-8:53 am

1 stop20h 14m

$435

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 8/15

8:30 pm-9:04 am

1 stop12h 34m

Boston Logan Intl

Sun 8/17

5:48 pm-8:53 am

1 stop15h 05m

$477

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Tue 9/16

7:30 am-5:17 pm

1 stop9h 47m

$162

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 9/22

6:30 am-2:15 pm

2 stops7h 45m

$164

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 8/14

9:18 am-11:53 am

1 stop26h 35m

$166

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 8/23

12:45 pm-9:37 am

1 stop20h 52m

$202

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 9/22

12:10 pm-11:13 am

3 stops23h 03m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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.

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Boston. Reviews last updated July 1, 2025.
Get a feel of what it's like to fly with Delta, JetBlue, and American Airlines from Westchester County to Boston by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
8.0
Very good
8.0
Very good

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
8.0
Very good

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
8.0
Very good

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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.

  • What are the cheapest airlines to fly from Westchester County to Boston one-way?

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $162. However, be on the lookout for offers from American Airlines and Cape Air, as they are both options that can get you from Westchester County to Boston for a low price.

  • 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 June is currently the most expensive (average of $306). 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 Westchester County?

Book flights to Westchester County if you plan to visit one of these locations
Cambridge
Medford
Watertown
Warwick
Seabrook
Waltham
Framingham
Cranston
Randolph
Chestnut Hill
Chelsea
Brockton
York Beach
Saco
Burlington
West Yarmouth
Smithfield
Swansea
Lincoln
Quincy

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