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Massachusetts

$94+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
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 February 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/2611:52 am
SWF
-
BOS
1 stop11h 52m
Multiple Airlines
Sun 3/19:57 am
BOS
-
SWF
1 stop7h 10m
Multiple Airlines
Deal found 2/3$324
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/67:33 pm
SWF
-
BOS
1 stop19h 05m
Multiple Airlines
Sun 2/85:23 pm
BOS
-
SWF
1 stop16h 56m
Multiple Airlines
Deal found 2/1$425
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/611:09 am
SWF
-
BOS
1 stop12h 48m
Multiple Airlines
Sat 2/76:39 pm
BOS
-
SWF
1 stop23h 20m
Multiple Airlines
Deal found 2/3$501
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2311:48 am
SWF
-
BOS
1 stop11h 26m
Multiple Airlines
Sun 6/285:27 pm
BOS
-
SWF
1 stop23h 38m
Multiple Airlines
Deal found 2/1$537
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/86:49 pm
SWF
-
BOS
1 stop22h 55m
Multiple Airlines
Sun 2/1510:01 am
BOS
-
SWF
2 stops24h 13m
Multiple Airlines
Deal found 2/3$545
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:02 pm
SWF
-
BOS
1 stop21h 25m
Multiple Airlines
Wed 2/186:10 pm
BOS
-
SWF
2 stops16h 58m
Multiple Airlines
Deal found 2/1$568
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/185:46 pm
SWF
-
ALB
1 stop24h 47m
Allegiant Air
Sun 2/227:23 pm
ALB
-
SWF
1 stop14h 51m
Allegiant Air
Deal found 2/2$583
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/2712:11 pm
SWF
-
BOS
2 stops9h 50m
Multiple Airlines
Sun 3/19:57 am
BOS
-
SWF
1 stop7h 10m
Multiple Airlines
Deal found 2/3$600
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/811:48 am
SWF
-
ALB
2 stops47h 45m
Multiple Airlines
Sun 2/156:51 pm
ALB
-
SWF
1 stop15h 23m
Multiple Airlines
Deal found 2/1$601
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/810:48 am
SWF
-
ALB
1 stop21h 59m
Allegiant Air
Sun 2/156:51 pm
ALB
-
SWF
1 stop15h 23m
Allegiant Air
Deal found 2/1$619
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/510:48 am
SWF
-
ALB
1 stop21h 59m
Allegiant Air
Thu 2/126:51 pm
ALB
-
SWF
1 stop15h 23m
Allegiant Air
Deal found 2/1$686

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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$324
(Kiwi.com)

One-way from

$94
(Kiwi.com)

Popular in

January

Cheapest in

November

Average price

$233
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
Search Deals
One-way flight from New Windsor Stewart to Massachusetts
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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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 February 4, 2026.
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

Thu 2/26

11:52 am-11:44 pm

1 stop11h 52m

Boston Logan Intl

Sun 3/1

9:57 am-5:07 pm

1 stop7h 10m

$324

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 2/15

6:02 pm-3:27 pm

1 stop21h 25m

Boston Logan Intl

Wed 2/18

6:10 pm-11:32 am

1 stop17h 22m

$516

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Tue 6/23

11:48 am-11:14 pm

1 stop11h 26m

Boston Logan Intl

Sun 6/28

5:27 pm-5:05 pm

1 stop23h 38m

$537

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Wed 2/18

5:46 pm-6:33 pm

1 stop24h 47m

Albany Intl

Sun 2/22

7:23 pm-10:14 am

1 stop14h 51m

$583

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 2/27

12:11 pm-10:01 pm

2 stops9h 50m

Boston Logan Intl

Sun 3/1

9:57 am-5:07 pm

1 stop7h 10m

$600

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 3/5

10:09 am-11:44 pm

1 stop13h 35m

$94

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 4/9

11:45 am-11:59 pm

1 stop12h 14m

$101

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 3/12

10:09 am-11:59 pm

1 stop13h 50m

$121

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 2/26

11:52 am-11:44 pm

1 stop11h 52m

$130

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 3/19

10:29 am-11:59 pm

1 stop13h 30m

$135

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 15 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, April is the cheapest month in which you can book a flight from New Windsor to Massachusetts (average of $88). 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 24h 47m. 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 - Hartford Bradley Intl and New Windsor Stewart - Albany 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, April is the cheapest month in which you can book a flight from New Windsor to Massachusetts (average of $88). 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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