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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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$229
(Mytrip)

One-way from

$111
(Mytrip)

Popular in

April

Cheapest in

September

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. 16% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This Mytrip deal was found by Cheapflights users on 7/27. 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 8/225:36 pmSWF - BOS
1 stop17h 42mMultiple Airlines
Mon 8/256:05 amBOS - SWF
1 stop10h 41mMultiple Airlines
Deal found 7/27$229
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Wed 8/137:06 pmSWF - ALB
1 stop13h 46mAllegiant Air
Sun 8/177:24 pmALB - SWF
1 stop15h 01mAllegiant Air
Deal found 7/29$363
This Mytrip deal was found by Cheapflights users on 7/27. 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 8/116:36 pmSWF - BDL
2 stops28h 53mMultiple Airlines
Fri 8/1511:17 amBDL - SWF
1 stop6h 15mMultiple Airlines
Deal found 7/27$481
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Wed 8/137:06 pmSWF - ALB
1 stop13h 46mMultiple Airlines
Sun 8/172:09 pmALB - SWF
3 stops22h 39mMultiple Airlines
Deal found 7/29$525

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 July 29, 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 8/22

5:36 pm-11:18 am

1 stop17h 42m

Boston Logan Intl

Mon 8/25

6:05 am-4:46 pm

1 stop10h 41m

$229

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Wed 8/13

7:06 pm-8:52 am

1 stop13h 46m

Albany Intl

Sun 8/17

7:24 pm-10:25 am

1 stop15h 01m

$363

New WindsorHartford

SWF - BDL

SWFBDL

New Windsor Stewart

Mon 8/11

6:36 pm-11:29 pm

2 stops28h 53m

Hartford Bradley Intl

Fri 8/15

11:17 am-5:32 pm

1 stop6h 15m

$481

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Wed 8/13

7:06 pm-8:52 am

1 stop13h 46m

Albany Intl

Sun 8/17

2:09 pm-12:48 pm

3 stops22h 39m

$525

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 8/22

5:36 pm-11:18 am

1 stop17h 42m

$111

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 8/31

12:13 pm-9:49 am

2 stops21h 36m

$205

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Sat 8/2

11:03 am-7:12 pm

1 stop8h 09m

$332

New WindsorHartford

SWF - BDL

SWFBDL

New Windsor Stewart

Mon 9/1

12:17 pm-8:27 pm

1 stop8h 10m

$337

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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.

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated July 29, 2025.
Read through reviews of airlines operating flights from New Windsor to Massachusetts, such as Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Allegiant Air
7.2
Good
703 reviews

Crew

8.1

Boarding

7.6

Entertainment

5.5

Comfort

6.8

Food

5.9

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.
Allegiant Air
7.2
Good
703 reviews
Allegiant Air
7.2
Good
703 reviews

Crew

8.1

Boarding

7.6

Entertainment

5.5

Comfort

6.8

Food

5.9

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.

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.

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