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$108+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PWM
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
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 August 20, 2025.

Round-trip from

$244
(Mytrip)

One-way from

$108
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$202
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. 13% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 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 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 August 20, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2411:31 amSWF - BOS
1 stop12h 28mMultiple Airlines
Mon 10/276:11 amBOS - SWF
1 stop8h 00mMultiple Airlines
Deal found 8/20$234
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.
Fri 10/312:11 pmSWF - BOS
1 stop11h 46mMultiple Airlines
Sun 10/58:24 pmBOS - SWF
1 stop13h 47mMultiple Airlines
Deal found 8/18$244
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.
Fri 10/1011:41 amSWF - BOS
1 stop23h 45mMultiple Airlines
Sun 10/128:24 pmBOS - SWF
1 stop13h 47mMultiple Airlines
Deal found 8/19$255
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.
Fri 10/1711:31 amSWF - BOS
1 stop23h 55mMultiple Airlines
Sun 10/199:55 amBOS - SWF
1 stop7h 00mMultiple Airlines
Deal found 8/19$293
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.
Fri 11/711:31 amSWF - BOS
1 stop13h 09mMultiple Airlines
Sun 11/93:56 pmBOS - SWF
1 stop25h 41mMultiple Airlines
Deal found 8/18$305
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.
Mon 9/111:02 amSWF - BOS
2 stops24h 12mMultiple Airlines
Thu 9/46:00 amBOS - SWF
1 stop7h 14mMultiple Airlines
Deal found 8/18$322
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/25:45 pmSWF - BOS
1 stop5h 25mMultiple Airlines
Sun 10/58:24 pmBOS - SWF
1 stop13h 47mMultiple Airlines
Deal found 8/20$331
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 10/301:35 pmSWF - BOS
1 stop7h 18mMultiple Airlines
Sun 11/28:24 pmBOS - SWF
1 stop14h 47mMultiple Airlines
Deal found 8/19$339
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.
Fri 8/2910:57 amSWF - BGR
1 stop30h 38mAllegiant Air
Sun 8/316:35 pmBGR - SWF
1 stop15h 37mAllegiant Air
Deal found 8/18$355
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.
Sat 8/307:29 pmSWF - BGR
1 stop23h 06mMultiple Airlines
Sat 9/135:34 pmBGR - SWF
1 stop24h 48mMultiple Airlines
Deal found 8/18$530
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.
Sat 8/307:29 pmSWF - BGR
1 stop23h 06mBreeze Airways
Thu 9/47:43 pmBGR - SWF
2 stops16h 01mBreeze Airways
Deal found 8/18$575
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/212:36 pmSWF - PWM
1 stop25h 50mBreeze Airways
Sat 9/63:21 pmPWM - SWF
1 stop19h 42mBreeze Airways
Deal found 8/18$591

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 August 20, 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

Fri 10/3

12:11 pm-11:57 pm

1 stop11h 46m

Boston Logan Intl

Sun 10/5

8:24 pm-10:11 am

1 stop13h 47m

$244

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

$255

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 11/7

11:31 am-12:40 am

1 stop13h 09m

Boston Logan Intl

Sun 11/9

6:57 pm-11:11 am

2 stops16h 14m

$293

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/17

11:31 am-11:26 am

1 stop23h 55m

Boston Logan Intl

Sun 10/19

9:55 am-4:55 pm

1 stop7h 00m

$293

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/24

11:31 am-11:26 am

1 stop23h 55m

Boston Logan Intl

Mon 10/27

9:55 am-5:49 pm

1 stop7h 54m

$302

New WindsorBangor

SWF - BGR

SWFBGR

New Windsor Stewart

Fri 8/29

10:57 am-5:35 pm

1 stop30h 38m

Bangor

Sun 8/31

6:35 pm-10:12 am

1 stop15h 37m

$355

New WindsorBangor

SWF - BGR

SWFBGR

New Windsor Stewart

Sat 8/30

7:29 pm-6:35 pm

1 stop23h 06m

Bangor

Sat 9/13

5:34 pm-6:22 pm

1 stop24h 48m

$530

New WindsorBangor

SWF - BGR

SWFBGR

New Windsor Stewart

Sat 8/30

7:29 pm-6:35 pm

1 stop23h 06m

Bangor

Thu 9/4

7:43 pm-11:44 am

2 stops16h 01m

$575

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Tue 9/2

12:36 pm-2:26 pm

1 stop25h 50m

Portland

Sat 9/6

3:21 pm-11:03 am

1 stop19h 42m

$591

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Sun 9/21

11:43 am-9:06 am

1 stop21h 23m

Portland

Wed 9/24

3:21 pm-11:03 am

1 stop19h 42m

$594

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 41 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 $575, Allegiant Air can have you in Maine from New Windsor in 23h 06m. There are 350 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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