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$88+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:40 amSWF - ALB
1 stop28h 22mAllegiant Air
Sun 1/411:42 amALB - SWF
1 stop21h 48mAllegiant Air
Deal found 12/16$732
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:40 amSWF - ALB
1 stop28h 22mMultiple Airlines
Sun 1/41:20 pmALB - SWF
2 stops21h 27mMultiple Airlines
Deal found 12/16$771
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Tue 12/2311:43 amSWF - BOS
1 stop22h 18mMultiple Airlines
Thu 12/2512:45 pmBOS - SWF
2 stops22h 22mMultiple Airlines
Deal found 12/17$784
This Mytrip deal was found by Cheapflights users on 12/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:25 pmSWF - BOS
1 stop14h 25mMultiple Airlines
Sun 12/2812:29 pmBOS - SWF
2 stops22h 18mMultiple Airlines
Deal found 12/16$864
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:25 pmSWF - BOS
1 stop27h 32mMultiple Airlines
Sat 12/277:34 pmBOS - SWF
2 stops15h 29mMultiple Airlines
Deal found 12/16$927
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2311:43 amSWF - BOS
1 stop22h 18mMultiple Airlines
Sat 12/277:34 pmBOS - SWF
2 stops15h 29mMultiple Airlines
Deal found 12/16$991

Find flight deals from Stewart to Massachusetts

Keep the following information in mind while searching for Stewart to Massachusetts flight deals. Data was last updated December 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$189
(Kiwi.com)

One-way from

$88
(Mytrip)

Popular in

April

Cheapest in

November

Average price

$225
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 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. 3% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 18, 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

Mon 2/2

7:33 pm-11:19 pm

1 stop27h 46m

Boston Logan Intl

Mon 2/9

7:00 am-6:43 pm

1 stop11h 43m

$189

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 1/19

11:09 am-1:03 am

2 stops37h 54m

Boston Logan Intl

Thu 1/29

5:27 pm-10:19 am

1 stop16h 52m

$213

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 3/5

10:09 am-11:57 pm

1 stop13h 48m

Boston Logan Intl

Sun 3/8

9:57 am-5:06 pm

1 stop7h 09m

$490

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Thu 1/15

10:48 am-8:47 am

1 stop21h 59m

Albany Intl

Sun 1/18

12:01 pm-10:19 am

2 stops22h 18m

$529

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Thu 1/15

10:48 am-8:47 am

1 stop21h 59m

Albany Intl

Sun 1/18

10:54 am-5:12 pm

1 stop30h 18m

$563

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Wed 12/31

10:40 am-3:02 pm

1 stop28h 22m

Albany Intl

Sun 1/4

11:42 am-9:30 am

1 stop21h 48m

$732

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 1/2

11:57 am-8:10 am

2 stops20h 13m

Boston Logan Intl

Sun 1/4

9:00 am-12:02 pm

2 stops27h 02m

$759

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Wed 12/31

10:40 am-3:02 pm

1 stop28h 22m

Albany Intl

Sun 1/4

1:20 pm-10:47 am

2 stops21h 27m

$771

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 1/26

11:09 am-11:57 pm

1 stop12h 48m

$88

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 2/2

7:33 pm-11:19 pm

1 stop27h 46m

$90

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 16 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, December is the cheapest month in which you can book a flight from New Windsor to Massachusetts (average of $78). Flying from New Windsor to Massachusetts in July is currently the most expensive (average of $170). 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.

  • How long is the flight from New Windsor to Massachusetts?

    There are many flights that can get you from New Windsor to Massachusetts in 21h 59m. Fly via Allegiant Air to get the fastest option. The distance from New Windsor to Massachusetts is about 88 mi.

  • 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 - Albany Intl, New Windsor Stewart - Boston Logan 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, December is the cheapest month in which you can book a flight from New Windsor to Massachusetts (average of $78). Flying from New Windsor to Massachusetts in July is currently the most expensive (average of $170). 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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