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$92+ Cheap flights from New Windsor (SWF) to Massachusetts

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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheap flight deals from Stewart to Massachusetts

Keep the following information in mind while searching for Stewart to Massachusetts flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$204
(Kiwi.com)

One-way from

$92
(Kiwi.com)

Popular in

April

Cheapest in

October

Average price

$197
From New Windsor Stewart to Massachusetts
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One-way flight from New Windsor Stewart to Massachusetts
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Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Stewart to Massachusetts

Cheapest flights from Stewart to Massachusetts
Explore the most affordable flight options available from Stewart to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/2011:01 amSWF - BOS
1 stop24h 25mMultiple Airlines
jue. 10/238:24 pmBOS - SWF
1 stop14h 17mMultiple Airlines
Deal found 9/14$204
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/3111:31 amSWF - BOS
1 stop12h 28mMultiple Airlines
dom. 11/28:24 pmBOS - SWF
1 stop14h 47mMultiple Airlines
Deal found 9/14$234
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
vie. 12/512:27 pmSWF - BOS
1 stop12h 13mMultiple Airlines
dom. 12/76:57 pmBOS - SWF
2 stops16h 40mMultiple Airlines
Deal found 9/15$276
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/2411:31 amSWF - BOS
1 stop23h 55mMultiple Airlines
dom. 10/269:55 amBOS - SWF
1 stop7h 00mMultiple Airlines
Deal found 9/14$286
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
vie. 10/1011:41 amSWF - BOS
1 stop23h 45mMultiple Airlines
dom. 10/128:24 pmBOS - SWF
1 stop13h 47mMultiple Airlines
Deal found 9/15$304
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/301:35 pmSWF - BOS
1 stop7h 18mMultiple Airlines
dom. 11/28:24 pmBOS - SWF
1 stop14h 47mMultiple Airlines
Deal found 9/14$314
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/312:11 pmSWF - BOS
1 stop11h 46mMultiple Airlines
dom. 10/59:55 amBOS - SWF
1 stop7h 00mMultiple Airlines
Deal found 9/14$317
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/312:11 pmSWF - BOS
1 stop11h 46mMultiple Airlines
lun. 10/69:55 amBOS - SWF
1 stop7h 33mMultiple Airlines
Deal found 9/14$318
This KAYAK deal was found by Cheapflights users on 9/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/1811:43 amSWF - BDL
2 stops11h 21mBreeze Airways
jue. 9/252:04 pmBDL - SWF
3 stops21h 40mBreeze Airways
Deal found 9/15$827

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Massachusetts 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 septiembre 16, 2025.
Use the filters below to find and compare flights from New Windsor to Massachusetts that are best for you.

Fly from

Stewart

Fly to

Massachusetts

Route

Depart

Return

Price

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

lun. 10/20

11:01 am-11:26 am

1 stop24h 25m

Boston Logan Intl

jue. 10/23

8:24 pm-10:41 am

1 stop14h 17m

$204

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

vie. 10/31

11:31 am-11:59 pm

1 stop12h 28m

Boston Logan Intl

dom. 11/2

8:24 pm-11:11 am

1 stop14h 47m

$234

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

vie. 10/24

11:31 am-11:26 am

1 stop23h 55m

Boston Logan Intl

dom. 10/26

9:55 am-4:55 pm

1 stop7h 00m

$286

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

vie. 10/10

11:41 am-11:26 am

1 stop23h 45m

Boston Logan Intl

dom. 10/12

8:24 pm-10:11 am

1 stop13h 47m

$304

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

jue. 10/30

1:35 pm-8:53 pm

1 stop7h 18m

Boston Logan Intl

dom. 11/2

8:24 pm-11:11 am

1 stop14h 47m

$314

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

vie. 10/3

12:11 pm-11:57 pm

1 stop11h 46m

Boston Logan Intl

dom. 10/5

9:55 am-4:55 pm

1 stop7h 00m

$317

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

vie. 10/3

12:11 pm-11:57 pm

1 stop11h 46m

Boston Logan Intl

lun. 10/6

9:55 am-5:28 pm

1 stop7h 33m

$318

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

vie. 10/17

11:31 am-11:59 pm

1 stop12h 28m

Boston Logan Intl

dom. 10/19

9:55 am-4:55 pm

1 stop7h 00m

$323

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

vie. 10/17

11:31 am-11:26 am

1 stop23h 55m

$92

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

lun. 11/3

12:01 pm-11:16 am

1 stop23h 15m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 18 results
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Best time to book a flight from Stewart to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Stewart 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 New Windsor to Massachusetts

What is the cheapest month to book a flight from New Windsor to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from New Windsor to Massachusetts (average of $218). Flying from New Windsor to Massachusetts 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.

Related info for your journey

Find useful and relevant information for your journey from Stewart to Massachusetts. 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 from for flights from New Windsor to Massachusetts?

    If you book a flight to Massachusetts from New Windsor, you will be flying from Stewart, which is the city’s only airport. New Windsor Stewart (SWF) is located 4.3 mi from the center of New Windsor.

  • What are the most popular routes from New Windsor to Massachusetts?

    The most popular flight routes from New Windsor to Massachusetts are New Windsor Stewart - Boston Logan Intl, New Windsor Stewart - Albany Intl and New Windsor Stewart - Hartford Bradley Intl.

  • Can I find deals for flights from Stewart to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Stewart to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Massachusetts.

  • Can I find deals for business class flights from Stewart to Massachusetts?

    Yes. Cheapflights offers flight deals from Stewart to Massachusetts 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 New Windsor to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Massachusetts (average of $218). Flying from New Windsor to Massachusetts 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

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