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Stewart

$111+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SWF
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheap flight deals from Massachusetts to Stewart

Keep the following information in mind while searching for Massachusetts to Stewart flight deals. Data was last updated July 30, 2025.

Round-trip from

$237
(Mytrip)

One-way from

$111
(Mytrip)

Popular in

June

Cheapest in

October

Average price

$193
From Massachusetts to New Windsor Stewart
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One-way flight from Massachusetts to New Windsor Stewart
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Highest demand for flights based on searches. 13% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 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 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 July 30, 2025.

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.
Mon 8/256:05 amBOS - SWF
1 stop10h 41mMultiple Airlines
Fri 8/291:55 pmSWF - BOS
1 stop9h 54mMultiple Airlines
Deal found 7/29$237
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/93:00 pmBDL - SWF
1 stop20h 44mBreeze Airways
Thu 10/1611:33 amSWF - BDL
2 stops11h 31mBreeze Airways
Deal found 7/30$566
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.
Mon 8/116:46 pmALB - SWF
2 stops17h 10mMultiple Airlines
Thu 8/147:52 pmSWF - ALB
2 stops22h 14mMultiple Airlines
Deal found 7/29$640

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 July 30, 2025.
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

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Mon 8/25

6:05 am-4:46 pm

1 stop10h 41m

New Windsor Stewart

Fri 8/29

1:55 pm-11:49 pm

1 stop9h 54m

$237

HartfordNew Windsor

BDL - SWF

BDLSWF

Hartford Bradley Intl

Thu 10/9

3:00 pm-11:44 am

1 stop20h 44m

New Windsor Stewart

Thu 10/16

11:33 am-11:04 pm

2 stops11h 31m

$566

AlbanyNew Windsor

ALB - SWF

ALBSWF

Albany Intl

Mon 8/11

6:46 pm-11:56 am

2 stops17h 10m

New Windsor Stewart

Thu 8/14

7:52 pm-6:06 pm

2 stops22h 14m

$640

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/9

8:03 pm-10:51 am

1 stop14h 48m

$111

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Fri 8/22

9:00 am-6:47 pm

2 stops9h 47m

$182

HartfordNew Windsor

BDL - SWF

BDLSWF

Hartford Bradley Intl

Sun 9/7

12:55 pm-11:44 am

3 stops22h 49m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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, October is the cheapest month in which you can book a flight from Massachusetts to New Windsor (average of $109). Flying from Massachusetts to New Windsor in August is currently the most expensive (average of $206). 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 Stewart

Get insights into the airlines that provide service to Stewart. 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 Stewart. Reviews last updated July 30, 2025.
Read through reviews of airlines operating flights from Massachusetts to New Windsor, such as Breeze Airways and Allegiant Air. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
191 reviews

Boarding

8.2

Comfort

8.1

Food

6.7

Entertainment

6.5

Overall

8.0

Crew

8.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.0
Very good
191 reviews
Breeze Airways
8.0
Very good
191 reviews

Boarding

8.2

Comfort

8.1

Food

6.7

Entertainment

6.5

Overall

8.0

Crew

8.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Allegiant Air
7.2
Good
703 reviews
Breeze Airways
8.0
Very good
191 reviews

Boarding

8.2

Comfort

8.1

Food

6.7

Entertainment

6.5

Overall

8.0

Crew

8.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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.

  • 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, October is the cheapest month in which you can book a flight from Massachusetts to New Windsor (average of $109). Flying from Massachusetts to New Windsor in August is currently the most expensive (average of $206). 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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