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Stewart

$94+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SWF
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$237
(Mytrip)

One-way from

$94
(Mytrip)

Popular in

February

Cheapest in

October

Average price

$197
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. 18% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/11. 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 6/276:15 amBOS - SWF
1 stop12h 56mMultiple Airlines
Mon 6/308:01 pmSWF - BOS
1 stop26h 55mMultiple Airlines
Deal found 6/11$237
This Mytrip deal was found by Cheapflights users on 6/10. 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 6/2510:21 amALB - SWF
1 stop24h 00mAllegiant Air
Sun 6/296:41 pmSWF - ALB
1 stop23h 17mAllegiant Air
Deal found 6/10$555
This Mytrip deal was found by Cheapflights users on 6/10. 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 6/2510:21 amALB - SWF
1 stop24h 00mMultiple Airlines
Sun 6/297:52 pmSWF - ALB
2 stops22h 06mMultiple Airlines
Deal found 6/10$669
This FlightHub deal was found by Cheapflights users on 6/10. 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.
Sun 6/158:05 amBDL - SWF
2 stops11h 07mBreeze Airways
Sun 6/227:52 pmSWF - BDL
2 stops21h 59mBreeze Airways
Deal found 6/10$868

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 June 12, 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

Fri 6/27

6:15 am-7:11 pm

1 stop12h 56m

New Windsor Stewart

Mon 6/30

8:01 pm-10:56 pm

1 stop26h 55m

$237

AlbanyNew Windsor

ALB - SWF

ALBSWF

Albany Intl

Wed 6/25

10:21 am-10:21 am

1 stop24h 00m

New Windsor Stewart

Sun 6/29

6:41 pm-5:58 pm

1 stop23h 17m

$555

AlbanyNew Windsor

ALB - SWF

ALBSWF

Albany Intl

Wed 6/25

10:21 am-10:21 am

1 stop24h 00m

New Windsor Stewart

Sun 6/29

7:52 pm-5:58 pm

2 stops22h 06m

$669

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Tue 7/1

4:44 pm-11:00 am

1 stop18h 16m

$94

HartfordNew Windsor

BDL - SWF

BDLSWF

Hartford Bradley Intl

Sun 6/22

8:50 am-5:56 pm

1 stop9h 06m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 $219). 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 June 12, 2025.
Allegiant Air
7.3
Good
725 reviews

Food

5.9

Entertainment

5.5

Overall

7.3

Boarding

7.6

Comfort

6.8

Crew

8.1

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
7.3
Good
725 reviews
Allegiant Air
7.3
Good
725 reviews

Food

5.9

Entertainment

5.5

Overall

7.3

Boarding

7.6

Comfort

6.8

Crew

8.1

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 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 $219). 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 Massachusetts?

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

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