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Stewart

$120+ Cheap flights from Maine 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SWF
Feb 17 — Feb 241
Tue 2/17
Tue 2/24
1 adult, Economy
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Cheap flight deals from Maine to Stewart

Keep the following information in mind while searching for Maine to Stewart flight deals. Data was last updated January 18, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$329
(Kiwi.com)

One-way from

$120
(Kiwi.com)

Popular in

November

Cheapest in

May

Average price

$234
Provider with most accurate pricing for Portland-New York (NYC) flight deals.
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From Maine to New Windsor Stewart
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One-way flight from Maine to New Windsor Stewart
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Highest demand for flights based on searches. 2% potential increase in price ($4 potential increase over avg. RT price).
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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 January 2026
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Find flight deals from Maine to Stewart

Cheapest flights from Maine to Stewart
Explore the most affordable flight options available from Maine to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 18, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/16. 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.
Wed 6/36:59 pm
BGR
-
SWF
2 stops13h 59m
Breeze Airways
Wed 6/1012:05 pm
SWF
-
BGR
1 stop6h 14m
Breeze Airways
Deal found 1/16$297
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 1/255:27 pm
BOS
-
SWF
1 stop16h 52m
Multiple Airlines
Sun 2/16:49 pm
SWF
-
BOS
1 stop22h 55m
Multiple Airlines
Deal found 1/18$319
This Kiwi.com deal was found by Cheapflights users on 1/17. 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 1/295:27 pm
BOS
-
SWF
1 stop16h 52m
Multiple Airlines
Sun 2/16:49 pm
SWF
-
BOS
1 stop22h 55m
Multiple Airlines
Deal found 1/17$329
This Kiwi.com deal was found by Cheapflights users on 1/17. 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 2/199:57 am
BOS
-
SWF
1 stop7h 15m
Multiple Airlines
Sun 2/2211:48 am
SWF
-
BOS
2 stops20h 53m
Multiple Airlines
Deal found 1/17$369
This Kiwi.com deal was found by Cheapflights users on 1/17. 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 1/307:00 am
BOS
-
SWF
1 stop11h 43m
Multiple Airlines
Sun 2/16:49 pm
SWF
-
BOS
1 stop22h 55m
Multiple Airlines
Deal found 1/17$373
This Kiwi.com deal was found by Cheapflights users on 1/16. 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.
Wed 1/216:18 pm
PWM
-
SWF
1 stop15h 40m
Multiple Airlines
Fri 1/237:33 pm
SWF
-
PWM
1 stop14h 49m
Multiple Airlines
Deal found 1/16$407
This Kiwi.com deal was found by Cheapflights users on 1/17. 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.
Sat 1/245:27 pm
BOS
-
SWF
2 stops18h 06m
Multiple Airlines
Sun 1/256:49 pm
SWF
-
BOS
1 stop22h 55m
Multiple Airlines
Deal found 1/17$435
This Kiwi.com deal was found by Cheapflights users on 1/16. 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 3/197:53 pm
BGR
-
SWF
1 stop12h 59m
Multiple Airlines
Sun 3/228:40 pm
SWF
-
BGR
1 stop21h 34m
Multiple Airlines
Deal found 1/16$521
This Booking.com deal was found by Cheapflights users on 1/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/293:51 pm
PWM
-
SWF
2 stops19h 34m
Breeze Airways
Sun 5/319:38 am
SWF
-
PWM
1 stop23h 34m
Breeze Airways
Deal found 1/16$543
This Booking.com deal was found by Cheapflights users on 1/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/123:51 pm
PWM
-
SWF
2 stops19h 34m
Breeze Airways
Sun 6/149:38 am
SWF
-
PWM
1 stop23h 34m
Breeze Airways
Deal found 1/16$551
This Kiwi.com deal was found by Cheapflights users on 1/17. 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 2/176:09 pm
BGR
-
SWF
1 stop22h 47m
Allegiant Air
Mon 2/2311:04 am
SWF
-
BGR
1 stop27h 59m
Allegiant Air
Deal found 1/17$584
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
Wed 4/223:32 pm
BGR
-
SWF
1 stop19h 23m
Allegiant Air
Sun 4/267:57 pm
SWF
-
BGR
1 stop23h 09m
Allegiant Air
Deal found 1/18$628

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maine 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 January 18, 2026.
Use the filters below to find and compare flights from Maine to New Windsor that are best for you.

Fly from

Maine

Fly to

Stewart

Route

Depart

Return

Price

BangorNew Windsor

BGR - SWF

BGRSWF

Bangor

Wed 6/3

6:59 pm-8:58 am

2 stops13h 59m

New Windsor Stewart

Wed 6/10

12:05 pm-6:19 pm

1 stop6h 14m

$297

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 1/29

5:27 pm-10:19 am

1 stop16h 52m

New Windsor Stewart

Sun 2/1

6:49 pm-5:44 pm

1 stop22h 55m

$329

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 2/19

9:57 am-5:12 pm

1 stop7h 15m

New Windsor Stewart

Sun 2/22

11:48 am-8:41 am

2 stops20h 53m

$369

BangorNew Windsor

BGR - SWF

BGRSWF

Bangor

Thu 3/19

7:53 pm-8:52 am

1 stop12h 59m

New Windsor Stewart

Sun 3/22

8:40 pm-6:14 pm

1 stop21h 34m

$521

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 5/29

3:51 pm-11:25 am

2 stops19h 34m

New Windsor Stewart

Sun 5/31

9:38 am-9:12 am

1 stop23h 34m

$543

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 6/12

3:51 pm-11:25 am

2 stops19h 34m

New Windsor Stewart

Sun 6/14

9:38 am-9:12 am

1 stop23h 34m

$551

BangorNew Windsor

BGR - SWF

BGRSWF

Bangor

Tue 2/17

6:09 pm-4:56 pm

1 stop22h 47m

New Windsor Stewart

Mon 2/23

11:04 am-3:03 pm

1 stop27h 59m

$584

BangorNew Windsor

BGR - SWF

BGRSWF

Bangor

Wed 4/22

3:32 pm-10:55 am

1 stop19h 23m

New Windsor Stewart

Sun 4/26

7:57 pm-7:06 pm

1 stop23h 09m

$628

BangorNew Windsor

BGR - SWF

BGRSWF

Bangor

Sat 2/21

11:01 am-7:34 pm

1 stop8h 33m

New Windsor Stewart

Mon 2/23

11:04 am-3:03 pm

1 stop27h 59m

$701

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 3/11

10:57 am-11:08 am

1 stop24h 11m

New Windsor Stewart

Sun 3/15

11:48 am-9:07 am

1 stop21h 19m

$798

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 34 results
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Best time to book a flight from Maine to Stewart

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

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

Currently, September is the cheapest month in which you can book a flight from Maine to New Windsor (average of $68). Flying from Maine to New Windsor in February is currently the most expensive (average of $157). 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 Maine 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 Maine?

    For a flight from Maine to New Windsor, you will be flying into Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city.

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

    Departing from Maine to New Windsor will take you 13h 59m. The distance from Maine to New Windsor is about 350 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Maine 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 Maine to New Windsor?

    Currently, September is the cheapest month in which you can book a flight from Maine to New Windsor (average of $68). Flying from Maine to New Windsor in February is currently the most expensive (average of $157). 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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