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$111+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
Nov 30 — Dec 71
Sun 11/30
Sun 12/7
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 October 31, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$251
(Kiwi.com)

One-way from

$111
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$207
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. 5% potential increase in price ($13 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 October 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 October 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/512:27 pmSWF - BOS
1 stop11h 29mMultiple Airlines
Sun 12/712:57 pmBOS - SWF
2 stops22h 40mMultiple Airlines
Deal found 10/30$251
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/87:30 pmSWF - BOS
1 stop14h 31mMultiple Airlines
Thu 12/118:11 pmBOS - SWF
2 stops15h 33mMultiple Airlines
Deal found 10/30$257
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/512:27 pmSWF - BOS
1 stop11h 29mMultiple Airlines
Thu 12/118:11 pmBOS - SWF
2 stops15h 33mMultiple Airlines
Deal found 10/30$262
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1411:01 amSWF - BOS
1 stop12h 58mMultiple Airlines
Sun 11/166:00 amBOS - SWF
1 stop6h 42mMultiple Airlines
Deal found 10/30$308
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1311:43 amSWF - BOS
1 stop20h 45mMultiple Airlines
Mon 11/176:00 amBOS - SWF
1 stop11h 37mMultiple Airlines
Deal found 10/29$323
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1012:01 pmSWF - BOS
1 stop11h 58mMultiple Airlines
Thu 11/1312:14 pmBOS - SWF
2 stops21h 57mMultiple Airlines
Deal found 10/30$388
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/131:32 pmSWF - BOS
1 stop10h 21mMultiple Airlines
Sun 11/166:00 amBOS - SWF
1 stop6h 42mMultiple Airlines
Deal found 10/29$391
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Sun 11/96:14 pmSWF - ALB
1 stop15h 09mAllegiant Air
Sun 11/161:43 pmALB - SWF
1 stop29h 09mAllegiant Air
Deal found 10/28$605

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 October 31, 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

Fri 12/5

12:27 pm-11:56 pm

1 stop11h 29m

Boston Logan Intl

Sun 12/7

12:57 pm-11:37 am

2 stops22h 40m

$251

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 12/8

7:30 pm-10:01 am

1 stop14h 31m

Boston Logan Intl

Thu 12/11

8:11 pm-11:44 am

2 stops15h 33m

$257

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 12/5

12:27 pm-11:56 pm

1 stop11h 29m

Boston Logan Intl

Thu 12/11

8:11 pm-11:44 am

2 stops15h 33m

$262

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 11/14

11:01 am-11:59 pm

1 stop12h 58m

Boston Logan Intl

Sun 11/16

6:00 am-12:42 pm

1 stop6h 42m

$308

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 11/13

11:43 am-8:28 am

1 stop20h 45m

Boston Logan Intl

Mon 11/17

6:00 am-5:37 pm

1 stop11h 37m

$323

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 12/15

12:27 pm-11:56 pm

1 stop11h 29m

Boston Logan Intl

Mon 12/22

8:08 am-7:35 pm

2 stops11h 27m

$326

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 11/10

12:01 pm-11:59 pm

1 stop11h 58m

Boston Logan Intl

Thu 11/13

12:14 pm-10:11 am

2 stops21h 57m

$388

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 11/13

1:32 pm-11:53 pm

1 stop10h 21m

Boston Logan Intl

Sun 11/16

6:00 am-12:42 pm

1 stop6h 42m

$391

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Sun 11/9

6:14 pm-9:23 am

1 stop15h 09m

Albany Intl

Sun 11/16

1:43 pm-6:52 pm

1 stop29h 09m

$605

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 2/2

7:33 pm-10:08 am

1 stop14h 35m

$112

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 22 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, November is the cheapest month in which you can book a flight from New Windsor to Massachusetts (average of $58). Flying from New Windsor to Massachusetts in July is currently the most expensive (average of $177). 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 15h 09m. 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 - 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, November is the cheapest month in which you can book a flight from New Windsor to Massachusetts (average of $58). Flying from New Windsor to Massachusetts in July is currently the most expensive (average of $177). 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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