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Stewart

$142+ Cheap flights from Massachusetts to New Windsor (SWF)

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.
BOS — SWF
Mar 4 — Mar 111
Wed 3/4
Wed 3/11
1 adult, Economy
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Cheap flight deals from Massachusetts to Stewart

Cheapest flights from Massachusetts to Stewart
Explore the most affordable flight options available from Massachusetts to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/31. 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 2/67:00 am
BOS
-
SWF
1 stop11h 43m
Multiple Airlines
Sun 2/86:49 pm
SWF
-
BOS
1 stop22h 55m
Multiple Airlines
Deal found 1/31$419
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 2/97:00 am
BOS
-
SWF
1 stop11h 43m
Multiple Airlines
Thu 2/1211:48 am
SWF
-
BOS
1 stop10h 13m
Multiple Airlines
Deal found 1/30$453
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 2/269:57 am
BOS
-
SWF
1 stop7h 10m
Multiple Airlines
Sun 3/111:48 am
SWF
-
BOS
1 stop10h 13m
Multiple Airlines
Deal found 1/31$483
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 2/156:51 pm
ALB
-
SWF
1 stop15h 23m
Allegiant Air
Thu 2/1912:22 pm
SWF
-
ALB
1 stop22h 20m
Allegiant Air
Deal found 1/31$500
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.
Mon 2/27:00 am
BOS
-
SWF
1 stop11h 43m
Multiple Airlines
Mon 2/911:09 am
SWF
-
BOS
1 stop12h 48m
Multiple Airlines
Deal found 2/1$556
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 2/156:51 pm
ALB
-
SWF
1 stop15h 23m
Multiple Airlines
Thu 2/1912:22 pm
SWF
-
ALB
2 stops28h 49m
Multiple Airlines
Deal found 1/31$557
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 2/129:57 am
BOS
-
SWF
1 stop7h 15m
Multiple Airlines
Mon 2/1611:04 am
SWF
-
BOS
1 stop10h 57m
Multiple Airlines
Deal found 2/1$583

Find flight deals from Massachusetts to Stewart

Keep the following information in mind while searching for Massachusetts to Stewart flight deals. Data was last updated February 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$483
(Kiwi.com)

One-way from

$142
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$208
Provider with most accurate pricing for Boston Logan Intl-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-New York (NYC) flights.
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From Massachusetts to New Windsor Stewart
Search Deals
One-way flight from Massachusetts to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in February 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Stewart 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 2, 2026.
Use the filters below to find and compare flights from Massachusetts to New Windsor that are best for you.

Fly from

Massachusetts

Fly to

Stewart

Route

Depart

Return

Price

AlbanyNew Windsor

ALB - SWF

ALBSWF

Albany Intl

Sun 2/15

6:51 pm-10:14 am

1 stop15h 23m

New Windsor Stewart

Thu 2/19

12:22 pm-10:42 am

1 stop22h 20m

$500

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 2/26

9:57 am-5:07 pm

1 stop7h 10m

New Windsor Stewart

Sun 3/1

11:48 am-10:01 pm

1 stop10h 13m

$535

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 2/12

9:57 am-5:12 pm

1 stop7h 15m

New Windsor Stewart

Mon 2/16

11:04 am-10:01 pm

1 stop10h 57m

$556

AlbanyNew Windsor

ALB - SWF

ALBSWF

Albany Intl

Sun 2/15

6:51 pm-10:14 am

1 stop15h 23m

New Windsor Stewart

Thu 2/19

12:22 pm-5:11 pm

2 stops28h 49m

$557

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Tue 3/24

6:29 pm-9:39 am

2 stops39h 10m

$152

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 3/1

4:22 pm-10:13 am

1 stop17h 51m

$156

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sat 2/28

12:47 pm-5:07 pm

1 stop28h 20m

$166

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Tue 5/26

6:29 pm-9:38 am

2 stops39h 09m

$169

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Tue 3/10

6:10 pm-11:08 am

2 stops40h 58m

$176

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Fri 5/8

11:16 am-11:25 am

2 stops24h 09m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 17 results
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Best time to book a flight from Massachusetts to Stewart

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

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

Currently, December is the cheapest month in which you can book a flight from Massachusetts to New Windsor (average of $77). Flying from Massachusetts to New Windsor in August is currently the most expensive (average of $120). 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 Massachusetts to Stewart. 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 New Windsor from Massachusetts?

    Located just 4.3 mi from the city center, New Windsor Stewart (SWF) is the airport most travelers will use when flying to New Windsor from Massachusetts.

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

    Airlines like Allegiant Air fly from Massachusetts to New Windsor in about 15h 23m. The time it takes to get you to your destination can typically vary by up to . The distance between Massachusetts and New Windsor is about 88 mi.

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

    Most travelers choose Boston Logan Intl - New Windsor Stewart, Hartford Bradley Intl - New Windsor Stewart or Albany Intl - New Windsor Stewart when deciding on the best route from Massachusetts to New Windsor.

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

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

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

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

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

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

    Currently, December is the cheapest month in which you can book a flight from Massachusetts to New Windsor (average of $77). Flying from Massachusetts to New Windsor in August is currently the most expensive (average of $120). 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 New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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