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$199+ 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 8/3. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — BOS
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$374
(JetBlue)

One-way from

$199
(Kiwi.com)

Popular in

April

Cheapest in

August

Average price

$181
Provider with most accurate pricing for New York (NYC)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Boston Logan Intl flights.
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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. 17% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This JetBlue deal was found by Cheapflights users on 4/30. 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.
Sat 6/79:00 amHPN - BOS
1 stop25h 54mJetBlue
Mon 6/98:35 pmBOS - HPN
1 stop26h 25mJetBlue
Deal found 4/30$374
This FlightHub deal was found by Cheapflights users on 5/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/299:18 amHPN - BOS
1 stop6h 06mCape Air
Thu 10/25:48 pmBOS - HPN
1 stop23h 03mCape Air
Deal found 5/1$406
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/133:06 pmHPN - BOS
1 stop17h 42mAmerican Airlines
Sat 7/266:09 amBOS - HPN
1 stop12h 12mAmerican Airlines
Deal found 4/30$494
This Mytrip deal was found by Cheapflights users on 5/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/299:20 amHPN - BOS
1 stop8h 24mMultiple Airlines
Fri 5/305:45 amBOS - HPN
2 stops30h 45mMultiple Airlines
Deal found 5/1$502

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 May 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

Sat 6/7

9:00 am-10:54 am

1 stop25h 54m

Boston Logan Intl

Mon 6/9

8:35 pm-11:00 pm

1 stop26h 25m

$374

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 9/29

9:18 am-3:24 pm

1 stop6h 06m

Boston Logan Intl

Thu 10/2

5:48 pm-4:51 pm

1 stop23h 03m

$406

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sun 7/13

3:06 pm-8:48 am

1 stop17h 42m

Boston Logan Intl

Sat 7/26

6:09 am-6:21 pm

1 stop12h 12m

$494

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 5/29

9:20 am-5:44 pm

1 stop8h 24m

Boston Logan Intl

Fri 5/30

5:45 am-12:30 pm

2 stops30h 45m

$502

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Sun 8/3

9:18 am-5:18 pm

1 stop8h 00m

$199

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Fri 6/6

9:00 am-4:05 pm

1 stop7h 05m

$212

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Mon 6/23

11:05 am-8:28 pm

2 stops9h 23m

$320

White PlainsBoston

HPN - BOS

HPNBOS

White Plains Westchester County

Thu 5/8

1:06 pm-7:03 am

2 stops17h 57m

$378

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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

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 May 1, 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 May 1, 2025.
Read reviews from past customers who have flown 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.
JetBlue
7.3
Good
2,923 reviews

Crew

8.0

Entertainment

7.3

Overall

7.3

Boarding

7.5

Comfort

7.6

Food

6.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2025

JFK - CHS

Boarding took a very long time, in fact we were delayed by at least 30mins. There wasn’t many options for snacks and there was only water. The pilot did an excellent job
JetBlue
7.3
Good
2,923 reviews
JetBlue
7.3
Good
2,923 reviews

Crew

8.0

Entertainment

7.3

Overall

7.3

Boarding

7.5

Comfort

7.6

Food

6.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2025

JFK - CHS

Boarding took a very long time, in fact we were delayed by at least 30mins. There wasn’t many options for snacks and there was only water. The pilot did an excellent job
American Airlines
7.2
Good
10,000 reviews
JetBlue
7.3
Good
2,923 reviews

Crew

8.0

Entertainment

7.3

Overall

7.3

Boarding

7.5

Comfort

7.6

Food

6.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2025

JFK - CHS

Boarding took a very long time, in fact we were delayed by at least 30mins. There wasn’t many options for snacks and there was only water. The pilot did an excellent job

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 Cape Air, with whom users have recently found tickets for as low as $199. However, be on the lookout for offers from JetBlue and American Airlines, 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 July is currently the most expensive (average of $310). 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
Marlborough
Warwick
Cambridge
Waltham
Framingham
Chestnut Hill
Randolph
Brockton
Lowell
Woburn
Somerville
York Beach
Saco
Burlington
West Yarmouth
Smithfield
Lincoln
Salem
Chelsea
Seabrook

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