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Stewart

$121+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SWF
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
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 August 20, 2025.

Round-trip from

$244
(Kiwi.com)

One-way from

$121
(Mytrip)

Popular in

February

Cheapest in

September

Average price

$173
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. 17% potential increase in price ($44 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 August 2025
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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 August 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/19. 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 10/308:24 pmBOS - SWF
1 stop14h 17mMultiple Airlines
Mon 11/312:01 pmSWF - BOS
1 stop23h 25mMultiple Airlines
Deal found 8/19$244
This Mytrip deal was found by Cheapflights users on 8/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/249:55 amBOS - SWF
1 stop7h 54mMultiple Airlines
Sun 10/265:45 pmSWF - BOS
1 stop15h 15mMultiple Airlines
Deal found 8/17$257
This Mytrip deal was found by Cheapflights users on 8/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/239:55 amBOS - SWF
1 stop7h 00mMultiple Airlines
Sun 10/265:45 pmSWF - BOS
1 stop15h 15mMultiple Airlines
Deal found 8/18$258
This Mytrip deal was found by Cheapflights users on 8/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:00 amBOS - SWF
1 stop11h 49mMultiple Airlines
Sun 10/55:45 pmSWF - BOS
1 stop15h 15mMultiple Airlines
Deal found 8/17$263
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Thu 9/116:00 amBOS - SWF
1 stop7h 14mMultiple Airlines
Mon 11/312:01 pmSWF - BOS
1 stop23h 25mMultiple Airlines
Deal found 8/18$268
This Mytrip deal was found by Cheapflights users on 8/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:24 pmBOS - SWF
1 stop14h 17mMultiple Airlines
Sun 10/195:45 pmSWF - BOS
1 stop15h 15mMultiple Airlines
Deal found 8/18$270
This Mytrip deal was found by Cheapflights users on 8/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/179:55 amBOS - SWF
1 stop7h 54mMultiple Airlines
Sun 10/195:45 pmSWF - BOS
1 stop15h 15mMultiple Airlines
Deal found 8/17$295
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 10/98:24 pmBOS - SWF
1 stop14h 27mMultiple Airlines
Mon 10/1311:01 amSWF - BOS
1 stop24h 25mMultiple Airlines
Deal found 8/19$300
This Mytrip deal was found by Cheapflights users on 8/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/216:00 amBOS - SWF
1 stop7h 14mMultiple Airlines
Sun 9/282:04 pmSWF - BOS
1 stop9h 06mMultiple Airlines
Deal found 8/18$314
This Mytrip deal was found by Cheapflights users on 8/19. 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 10/319:55 amBOS - SWF
1 stop7h 54mMultiple Airlines
Sun 11/21:35 pmSWF - BOS
1 stop7h 18mMultiple Airlines
Deal found 8/19$320
This Gotogate deal was found by Cheapflights users on 8/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/173:21 pmPWM - SWF
1 stop19h 42mBreeze Airways
Sun 9/2111:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Deal found 8/20$584
This Gotogate deal was found by Cheapflights users on 8/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Sun 9/711:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Deal found 8/18$639

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 August 20, 2025.
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

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/30

8:24 pm-10:41 am

1 stop14h 17m

New Windsor Stewart

Mon 11/3

12:01 pm-11:26 am

1 stop23h 25m

$244

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Fri 10/24

9:55 am-5:49 pm

1 stop7h 54m

New Windsor Stewart

Sun 10/26

5:45 pm-9:00 am

1 stop15h 15m

$257

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/23

9:55 am-4:55 pm

1 stop7h 00m

New Windsor Stewart

Sun 10/26

5:45 pm-9:00 am

1 stop15h 15m

$258

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Fri 10/3

6:00 am-5:49 pm

1 stop11h 49m

New Windsor Stewart

Sun 10/5

5:45 pm-9:00 am

1 stop15h 15m

$263

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 9/11

6:00 am-1:14 pm

1 stop7h 14m

New Windsor Stewart

Mon 11/3

12:01 pm-11:26 am

1 stop23h 25m

$268

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/16

8:24 pm-10:41 am

1 stop14h 17m

New Windsor Stewart

Sun 10/19

5:45 pm-9:00 am

1 stop15h 15m

$270

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Fri 10/17

9:55 am-5:49 pm

1 stop7h 54m

New Windsor Stewart

Sun 10/19

5:45 pm-9:00 am

1 stop15h 15m

$295

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/9

8:24 pm-10:51 am

1 stop14h 27m

New Windsor Stewart

Mon 10/13

11:01 am-11:26 am

1 stop24h 25m

$300

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 9/21

6:00 am-1:14 pm

1 stop7h 14m

New Windsor Stewart

Sun 9/28

2:04 pm-11:10 pm

1 stop9h 06m

$314

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Fri 10/31

9:55 am-5:49 pm

1 stop7h 54m

New Windsor Stewart

Sun 11/2

1:35 pm-8:53 pm

1 stop7h 18m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 43 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, October is the cheapest month in which you can book a flight from Maine to New Windsor (average of $109). Flying from Maine to New Windsor in December is currently the most expensive (average of $202). 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 19h 42m. The distance from Maine to New Windsor is about 243 mi.

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

    Most travelers choose Boston Logan Intl - New Windsor Stewart, Portland - 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, October is the cheapest month in which you can book a flight from Maine to New Windsor (average of $109). Flying from Maine to New Windsor in December is currently the most expensive (average of $202). 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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