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Maine

$114+ 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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PWM
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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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 November 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/127:30 pmSWF - BOS
1 stop14h 31mMultiple Airlines
Sat 12/138:11 pmBOS - SWF
1 stop14h 52mMultiple Airlines
Deal found 11/4$231
This Kiwi.com deal was found by Cheapflights users on 11/3. 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
Sat 12/68:11 pmBOS - SWF
1 stop14h 52mMultiple Airlines
Deal found 11/3$238
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/57:30 pmSWF - PWM
1 stop15h 06mMultiple Airlines
Sat 12/66:18 pmPWM - SWF
1 stop16h 01mMultiple Airlines
Deal found 11/4$318
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/1311:43 amSWF - BOS
1 stop24h 21mMultiple Airlines
Sun 11/166:16 amBOS - SWF
1 stop28h 55mMultiple Airlines
Deal found 11/3$359
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Fri 11/1411:01 amSWF - BOS
1 stop12h 58mMultiple Airlines
Sun 11/166:00 amBOS - SWF
1 stop6h 42mMultiple Airlines
Deal found 11/2$391
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2612:17 pmSWF - BOS
1 stop11h 36mMultiple Airlines
Thu 11/276:00 amBOS - SWF
1 stop6h 23mMultiple Airlines
Deal found 11/4$407
This Mytrip deal was found by Cheapflights users on 11/1. 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 11/161:32 pmSWF - BOS
1 stop10h 21mMultiple Airlines
Thu 11/206:00 amBOS - SWF
1 stop11h 33mMultiple Airlines
Deal found 11/1$423
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:25 pmSWF - BOS
1 stop14h 25mMultiple Airlines
Sun 12/2812:29 pmBOS - SWF
2 stops22h 18mMultiple Airlines
Deal found 11/3$479
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/259:33 amSWF - BGR
1 stop9h 20mMultiple Airlines
Wed 11/2611:12 amBGR - SWF
1 stop7h 23mMultiple Airlines
Deal found 11/3$515
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/267:25 pmSWF - BGR
1 stop23h 38mMultiple Airlines
Sat 11/296:30 pmBGR - SWF
1 stop17h 31mMultiple Airlines
Deal found 11/2$598
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/225:28 pmSWF - BGR
1 stop24h 19mAllegiant Air
Sat 12/2710:40 amBGR - SWF
1 stop9h 15mAllegiant Air
Deal found 11/1$649
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/278:45 pmSWF - BGR
1 stop20h 03mMultiple Airlines
Thu 1/17:43 pmBGR - SWF
2 stops16h 01mMultiple Airlines
Deal found 11/1$663

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 November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$231
(Kiwi.com)

One-way from

$114
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$263
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 ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 4, 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 12/5

7:30 pm-10:01 am

1 stop14h 31m

Boston Logan Intl

Sat 12/6

8:11 pm-11:03 am

1 stop14h 52m

$238

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 12/5

7:30 pm-10:36 am

1 stop15h 06m

Portland

Sat 12/6

6:18 pm-10:19 am

1 stop16h 01m

$318

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 11/13

11:43 am-8:28 am

1 stop20h 45m

Boston Logan Intl

Sun 11/16

8:40 am-11:11 am

2 stops26h 31m

$371

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 11/14

11:01 am-11:59 pm

1 stop12h 58m

Boston Logan Intl

Sun 11/16

6:00 am-12:42 pm

1 stop6h 42m

$391

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Wed 11/26

12:17 pm-11:53 pm

1 stop11h 36m

Boston Logan Intl

Thu 11/27

6:00 am-12:23 pm

1 stop6h 23m

$407

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 11/16

1:32 pm-11:53 pm

1 stop10h 21m

Boston Logan Intl

Thu 11/20

6:00 am-5:33 pm

1 stop11h 33m

$423

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 12/22

8:25 pm-10:50 am

1 stop14h 25m

Boston Logan Intl

Sun 12/28

12:29 pm-10:47 am

2 stops22h 18m

$479

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 11/7

5:50 pm-12:41 pm

2 stops18h 51m

Boston Logan Intl

Sun 11/9

6:00 am-12:42 pm

1 stop6h 42m

$480

New WindsorBangor

SWF - BGR

SWFBGR

New Windsor Stewart

Tue 11/25

9:33 am-6:53 pm

1 stop9h 20m

Bangor

Wed 11/26

11:12 am-6:35 pm

1 stop7h 23m

$515

New WindsorBangor

SWF - BGR

SWFBGR

New Windsor Stewart

Wed 11/26

7:25 pm-7:03 pm

1 stop23h 38m

Bangor

Sat 11/29

6:30 pm-12:01 pm

1 stop17h 31m

$598

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

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, 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 $748, Allegiant Air can have you in Maine from New Windsor in 22h 12m. 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 - 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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