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Maine

$100+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PWM
Jan 4 — Jan 111
Sun 1/4
Sun 1/11
1 adult, Economy
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Cheap 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 December 5, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/1212:27 pmSWF - BOS
1 stop11h 29mMultiple Airlines
Sun 12/1412:57 pmBOS - SWF
2 stops22h 47mMultiple Airlines
Deal found 12/3$212
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/1212:27 pmSWF - BOS
1 stop11h 29mMultiple Airlines
Sat 12/138:11 pmBOS - SWF
1 stop14h 52mMultiple Airlines
Deal found 12/4$255
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/198:11 pmSWF - BGR
1 stop15h 24mMultiple Airlines
Tue 12/237:43 pmBGR - SWF
1 stop21h 01mMultiple Airlines
Deal found 12/3$328
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/1811:43 amSWF - BGR
1 stop22h 52mMultiple Airlines
Tue 12/237:43 pmBGR - SWF
1 stop21h 01mMultiple Airlines
Deal found 12/3$345
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/2311:43 amSWF - BOS
1 stop22h 18mMultiple Airlines
Sun 1/412:22 pmBOS - SWF
1 stop23h 40mMultiple Airlines
Deal found 12/3$351
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/57:30 pmSWF - BOS
1 stop14h 31mMultiple Airlines
Sun 12/78:11 pmBOS - SWF
1 stop22h 29mMultiple Airlines
Deal found 12/3$356
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/198:11 pmSWF - BGR
1 stop15h 24mMultiple Airlines
Wed 12/246:10 pmBGR - SWF
1 stop16h 53mMultiple Airlines
Deal found 12/3$378
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/245:34 pmSWF - BGR
1 stop22h 31mMultiple Airlines
Sun 12/287:43 pmBGR - SWF
1 stop16h 19mMultiple Airlines
Deal found 12/2$475
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/2311:43 amSWF - BGR
1 stop29h 37mMultiple Airlines
Wed 12/316:10 pmBGR - SWF
1 stop16h 53mMultiple Airlines
Deal found 12/4$486
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/2311:43 amSWF - BGR
1 stop29h 37mMultiple Airlines
Sun 12/287:43 pmBGR - SWF
1 stop16h 19mMultiple Airlines
Deal found 12/2$515
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/198:11 pmSWF - PWM
1 stop14h 25mMultiple Airlines
Mon 12/299:46 amPWM - SWF
1 stop25h 17mMultiple Airlines
Deal found 12/4$578
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/2111:43 amSWF - BGR
1 stop22h 52mMultiple Airlines
Wed 12/316:10 pmBGR - SWF
1 stop16h 53mMultiple Airlines
Deal found 12/4$594

Find flight deals from Stewart to Maine

Keep the following information in mind while searching for Stewart to Maine flight deals. Data was last updated December 5, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$207
(Mytrip)

One-way from

$100
(Kiwi.com)

Popular in

November

Cheapest in

April

Average price

$278
Provider with most accurate pricing for New York (NYC)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Portland flights.
Search Deals
From New Windsor Stewart to Maine
Search Deals
One-way flight from New Windsor Stewart to Maine
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 5, 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 1/9

11:09 am-11:57 pm

1 stop12h 48m

Boston Logan Intl

Sun 1/11

5:27 pm-10:19 am

1 stop16h 52m

$207

New WindsorBangor

SWF - BGR

SWFBGR

New Windsor Stewart

Fri 12/19

8:11 pm-11:35 am

1 stop15h 24m

Bangor

Tue 12/23

7:43 pm-4:44 pm

1 stop21h 01m

$328

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 1/11

12:13 pm-11:19 pm

1 stop11h 06m

Boston Logan Intl

Thu 1/15

5:27 pm-10:19 am

1 stop16h 52m

$329

New WindsorBangor

SWF - BGR

SWFBGR

New Windsor Stewart

Thu 12/18

11:43 am-10:35 am

1 stop22h 52m

Bangor

Tue 12/23

7:43 pm-4:44 pm

1 stop21h 01m

$345

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Tue 12/23

11:43 am-10:01 am

1 stop22h 18m

Boston Logan Intl

Sun 1/4

12:22 pm-12:02 pm

1 stop23h 40m

$351

New WindsorBangor

SWF - BGR

SWFBGR

New Windsor Stewart

Fri 12/19

8:11 pm-11:35 am

1 stop15h 24m

Bangor

Wed 12/24

6:10 pm-11:03 am

1 stop16h 53m

$378

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 1/5

11:37 am-11:57 pm

1 stop12h 20m

Boston Logan Intl

Thu 1/8

5:27 pm-10:19 am

1 stop16h 52m

$400

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 1/2

11:57 am-11:57 pm

1 stop12h 00m

Boston Logan Intl

Fri 1/9

7:00 am-6:43 pm

1 stop11h 43m

$421

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 12/22

8:25 pm-10:50 am

1 stop14h 25m

Boston Logan Intl

Sun 1/4

12:29 pm-10:47 am

2 stops22h 18m

$453

New WindsorBangor

SWF - BGR

SWFBGR

New Windsor Stewart

Wed 12/24

5:34 pm-4:05 pm

1 stop22h 31m

Bangor

Sun 12/28

7:43 pm-12:02 pm

1 stop16h 19m

$475

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 42 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, April is the cheapest month in which you can book a flight from New Windsor to Maine (average of $58). Flying from New Windsor to Maine in February is currently the most expensive (average of $206). 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 $675, Breeze Airways can have you in Maine from New Windsor in 21h 23m. There are 243 mi between New Windsor and Maine.

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

    Most travelers choose New Windsor Stewart - Boston Logan Intl, New Windsor Stewart - Portland 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, April is the cheapest month in which you can book a flight from New Windsor to Maine (average of $58). Flying from New Windsor to Maine in February is currently the most expensive (average of $206). 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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