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$92+ Cheap flights from New Windsor (SWF) to Maine

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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PWM
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Stewart to Maine

Keep the following information in mind while searching for Stewart to Maine flight deals. Data was last updated September 15, 2025.

Round-trip from

$204
(Kiwi.com)

One-way from

$92
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$223
From New Windsor Stewart to Maine
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One-way flight from New Windsor Stewart to Maine
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Highest demand for flights based on searches. 10% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Stewart to Maine

Cheapest flights from Stewart to Maine
Explore the most affordable flight options available from Stewart to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/2011:01 amSWF - BOS
1 stop24h 25mMultiple Airlines
Thu 10/238:24 pmBOS - SWF
1 stop14h 17mMultiple Airlines
Deal found 9/14$204
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/3111:31 amSWF - BOS
1 stop12h 28mMultiple Airlines
Sun 11/28:24 pmBOS - SWF
1 stop14h 47mMultiple Airlines
Deal found 9/14$234
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/512:27 pmSWF - BOS
1 stop12h 13mMultiple Airlines
Sun 12/76:57 pmBOS - SWF
2 stops16h 40mMultiple Airlines
Deal found 9/15$276
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/2411:31 amSWF - BOS
1 stop23h 55mMultiple Airlines
Sun 10/269:55 amBOS - SWF
1 stop7h 00mMultiple Airlines
Deal found 9/14$286
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/301:35 pmSWF - BOS
1 stop7h 18mMultiple Airlines
Sun 11/28:24 pmBOS - SWF
1 stop14h 47mMultiple Airlines
Deal found 9/14$314
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/312:11 pmSWF - BOS
1 stop11h 46mMultiple Airlines
Sun 10/59:55 amBOS - SWF
1 stop7h 00mMultiple Airlines
Deal found 9/14$317
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/312:11 pmSWF - BOS
1 stop11h 46mMultiple Airlines
Mon 10/69:55 amBOS - SWF
1 stop7h 33mMultiple Airlines
Deal found 9/14$318
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/1011:41 amSWF - BOS
1 stop23h 45mMultiple Airlines
Sun 10/128:24 pmBOS - SWF
1 stop13h 47mMultiple Airlines
Deal found 9/15$320
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/1411:16 amSWF - BGR
1 stop23h 57mAllegiant Air
Sun 10/1912:04 pmBGR - SWF
1 stop31h 27mAllegiant Air
Deal found 9/15$349
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/711:16 amSWF - BGR
1 stop23h 57mAllegiant Air
Sun 10/1212:04 pmBGR - SWF
1 stop31h 27mAllegiant Air
Deal found 9/15$427
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 9/2811:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Thu 10/25:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Deal found 9/13$431
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/2511:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Sun 9/285:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Deal found 9/14$455

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Maine 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 September 15, 2025.
Use the filters below to find and compare flights from New Windsor to Maine that are best for you.

Fly from

Stewart

Fly to

Maine

Route

Depart

Return

Price

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 10/20

11:01 am-11:26 am

1 stop24h 25m

Boston Logan Intl

Thu 10/23

8:24 pm-10:41 am

1 stop14h 17m

$204

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/31

11:31 am-11:59 pm

1 stop12h 28m

Boston Logan Intl

Sun 11/2

8:24 pm-11:11 am

1 stop14h 47m

$234

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/24

11:31 am-11:26 am

1 stop23h 55m

Boston Logan Intl

Sun 10/26

9:55 am-4:55 pm

1 stop7h 00m

$286

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 10/30

1:35 pm-8:53 pm

1 stop7h 18m

Boston Logan Intl

Sun 11/2

8:24 pm-11:11 am

1 stop14h 47m

$314

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/3

12:11 pm-11:57 pm

1 stop11h 46m

Boston Logan Intl

Sun 10/5

9:55 am-4:55 pm

1 stop7h 00m

$317

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/3

12:11 pm-11:57 pm

1 stop11h 46m

Boston Logan Intl

Mon 10/6

9:55 am-5:28 pm

1 stop7h 33m

$318

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/10

11:41 am-11:26 am

1 stop23h 45m

Boston Logan Intl

Sun 10/12

8:24 pm-10:11 am

1 stop13h 47m

$320

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/17

11:31 am-11:59 pm

1 stop12h 28m

Boston Logan Intl

Sun 10/19

9:55 am-4:55 pm

1 stop7h 00m

$323

New WindsorBangor

SWF - BGR

SWFBGR

New Windsor Stewart

Tue 10/14

11:16 am-11:13 am

1 stop23h 57m

Bangor

Sun 10/19

12:04 pm-7:31 pm

1 stop31h 27m

$349

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Sun 9/28

11:43 am-9:06 am

1 stop21h 23m

Portland

Thu 10/2

5:40 pm-11:44 am

2 stops18h 04m

$431

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 50 results
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Best time to book a flight from Stewart to Maine

Have a flexible travel schedule? Discover the best time to fly to Maine 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 Maine

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

Currently, January is the cheapest month in which you can book a flight from New Windsor to Maine (average of $296). Flying from New Windsor to Maine in July is currently the most expensive (average of $394). 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 Maine. 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 Maine?

    New Windsor Stewart (SWF), located 4.3 mi from the city center, is the airport you fly out of when you book flights from New Windsor to Maine.

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

    For as low as $431, Allegiant Air can have you in Maine from New Windsor in 21h 23m. There are 243 mi between New Windsor and Maine. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Most travelers choose New Windsor Stewart - Portland, New Windsor Stewart - Boston Logan Intl or New Windsor Stewart - Bangor when deciding on the best route from New Windsor to Maine.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to Maine 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 Maine?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Maine (average of $296). Flying from New Windsor to Maine in July is currently the most expensive (average of $394). 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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