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$140+ 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 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$241
(American Airlines)

One-way from

$140
(American Airlines)

Popular in

April

Cheapest in

October

Average price

$216
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. 19% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 18, 2025.

This American Airlines deal was found by Cheapflights users on 6/16. 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.
Mon 7/216:37 amHPN - BOS
2 stops7h 30mAmerican Airlines
Mon 7/215:00 pmBOS - HPN
1 stop6h 28mAmerican Airlines
Deal found 6/16$241
This JetBlue deal was found by Cheapflights users on 6/16. 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 9/49:00 amHPN - BOS
1 stop7h 08mJetBlue
Thu 9/111:20 pmBOS - HPN
1 stop9h 10mJetBlue
Deal found 6/16$343
This Booking.com deal was found by Cheapflights users on 6/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/249:18 amHPN - BOS
1 stop8h 00mCape Air
Wed 6/258:43 amBOS - HPN
1 stop8h 08mCape Air
Deal found 6/16$437
This JetBlue Airways deal was found by Cheapflights users on 6/16. 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.
Sat 7/127:30 amHPN - BOS
1 stop25h 35mMultiple Airlines
Sun 7/1312:39 pmBOS - HPN
1 stop4h 12mMultiple Airlines
Deal found 6/16$456

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 June 18, 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

Mon 7/21

6:37 am-2:07 pm

2 stops7h 30m

Boston Logan Intl

Mon 7/21

5:00 pm-11:28 pm

1 stop6h 28m

$241

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 9/4

9:00 am-4:08 pm

1 stop7h 08m

Boston Logan Intl

Thu 9/11

1:20 pm-10:30 pm

1 stop9h 10m

$343

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 7/21

9:18 am-3:24 pm

1 stop6h 06m

Boston Logan Intl

Mon 7/21

5:48 pm-4:51 pm

1 stop23h 03m

$441

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 7/12

7:30 am-9:05 am

1 stop25h 35m

Boston Logan Intl

Sun 7/13

12:39 pm-4:51 pm

1 stop4h 12m

$456

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sat 7/26

12:55 pm-7:44 pm

1 stop6h 49m

Boston Logan Intl

Sun 7/27

5:15 am-11:57 am

1 stop6h 42m

$1,471

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 7/16

6:37 am-2:07 pm

2 stops7h 30m

$140

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Wed 7/16

7:30 am-2:43 pm

1 stop7h 13m

$197

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sun 11/30

5:20 pm-10:59 am

1 stop17h 39m

$200

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 8/7

1:06 pm-7:53 pm

3 stops30h 47m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

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

What is the cheapest time of day to fly from REU to BOS?

Find hourly flight availability from Westchester County to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 18, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Westchester County to Boston as you normally would.

Rainfall in Boston by month

Plan your trip to Boston by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.

Temperature in Boston by month

Plan your trip to Boston by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Boston, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 June 18, 2025.
Read reviews from past customers who have flown Delta, JetBlue and American Airlines from Westchester County to Boston. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,964 reviews

Boarding

8.2

Entertainment

7.9

Overall

8.0

Crew

8.5

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.
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Boarding

8.2

Entertainment

7.9

Overall

8.0

Crew

8.5

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.
JetBlue
7.3
Good
2,923 reviews
Delta
8.0
Very good
7,964 reviews

Boarding

8.2

Entertainment

7.9

Overall

8.0

Crew

8.5

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.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,964 reviews

Boarding

8.2

Entertainment

7.9

Overall

8.0

Crew

8.5

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 American Airlines, with whom users have recently found tickets for as low as $140. However, be on the lookout for offers from JetBlue 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
Waltham
Framingham
Seabrook
Cranston
Randolph
Chestnut Hill
Lowell
Chelsea
Brockton
York Beach
Saco
Burlington
West Yarmouth
Smithfield
Swansea
Lincoln

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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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