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Stewart

$95+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SWF
Jan 4 — Jan 111
Sun 1/4
Sun 1/11
1 adult, Economy
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Cheap 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 December 5, 2025.

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.
Sun 12/78:11 pmBOS - SWF
1 stop22h 29mMultiple Airlines
Wed 12/245:34 pmSWF - BOS
1 stop16h 18mMultiple Airlines
Deal found 12/2$339
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.
Thu 12/117:43 pmBGR - SWF
2 stops16h 01mMultiple Airlines
Sun 12/1411:09 amSWF - BGR
1 stop8h 00mMultiple Airlines
Deal found 12/2$367
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.
Thu 12/1111:28 amBOS - SWF
2 stops24h 09mMultiple Airlines
Sun 12/1411:43 amSWF - BOS
1 stop22h 20mMultiple Airlines
Deal found 12/4$401
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.
Thu 12/1111:28 amBOS - SWF
2 stops24h 09mMultiple Airlines
Fri 12/127:30 pmSWF - BOS
1 stop14h 31mMultiple Airlines
Deal found 12/4$414
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.
Wed 12/108:11 pmBOS - SWF
1 stop14h 52mMultiple Airlines
Sun 1/1112:13 pmSWF - BOS
1 stop11h 06mMultiple Airlines
Deal found 12/3$501
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 12/1911:25 amBGR - SWF
1 stop21h 30mAllegiant Air
Tue 12/234:50 pmSWF - BGR
1 stop17h 35mAllegiant Air
Deal found 12/4$602
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.
Sat 12/206:18 pmPWM - SWF
1 stop16h 01mMultiple Airlines
Tue 12/2311:43 amSWF - PWM
1 stop22h 53mMultiple Airlines
Deal found 12/4$620
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/229:46 amPWM - SWF
1 stop25h 17mBreeze Airways
Sun 1/2512:13 pmSWF - PWM
1 stop20h 54mBreeze Airways
Deal found 12/3$622
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 12/118:11 pmBOS - SWF
2 stops15h 33mMultiple Airlines
Sun 1/1112:13 pmSWF - BOS
1 stop11h 06mMultiple Airlines
Deal found 12/3$623
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.
Thu 12/47:43 pmBGR - SWF
2 stops16h 01mMultiple Airlines
Sun 12/711:09 amSWF - BGR
1 stop8h 00mMultiple Airlines
Deal found 12/2$637
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.
Sat 12/2010:56 amBOS - SWF
1 stop24h 07mMultiple Airlines
Wed 12/2410:40 amSWF - BOS
2 stops25h 15mMultiple Airlines
Deal found 12/4$639
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.
Sat 12/68:11 pmBOS - SWF
1 stop14h 52mMultiple Airlines
Mon 12/87:30 pmSWF - BOS
1 stop14h 31mMultiple Airlines
Deal found 12/4$685

Find flight deals from Maine to Stewart

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(Kiwi.com)

One-way from

$95
(Kiwi.com)

Popular in

November

Cheapest in

May

Average price

$237
Provider with most accurate pricing for Portland-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-New York (NYC) flights.
Search Deals
From Maine to New Windsor Stewart
Search Deals
One-way flight from Maine to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% 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 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 December 5, 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 1/8

5:27 pm-10:19 am

1 stop16h 52m

New Windsor Stewart

Mon 1/12

7:33 pm-2:38 pm

1 stop19h 05m

$189

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 1/22

5:27 pm-10:19 am

1 stop16h 52m

New Windsor Stewart

Mon 1/26

11:09 am-11:57 pm

1 stop12h 48m

$203

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 1/8

5:27 pm-10:19 am

1 stop16h 52m

New Windsor Stewart

Fri 1/23

11:09 am-11:57 pm

1 stop12h 48m

$232

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Fri 1/16

7:00 am-6:43 pm

1 stop11h 43m

New Windsor Stewart

Mon 1/19

11:09 am-11:57 pm

1 stop12h 48m

$319

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 1/28

6:18 pm-9:58 am

1 stop15h 40m

New Windsor Stewart

Sun 2/1

12:13 pm-9:07 am

1 stop20h 54m

$511

BangorNew Windsor

BGR - SWF

BGRSWF

Bangor

Fri 12/19

11:25 am-8:55 am

1 stop21h 30m

New Windsor Stewart

Tue 12/23

4:50 pm-10:25 am

1 stop17h 35m

$602

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 12/20

6:18 pm-10:19 am

1 stop16h 01m

New Windsor Stewart

Tue 12/23

11:43 am-10:36 am

1 stop22h 53m

$620

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Mon 12/22

9:46 am-11:03 am

1 stop25h 17m

New Windsor Stewart

Sun 1/25

12:13 pm-9:07 am

1 stop20h 54m

$622

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sat 12/20

10:56 am-11:03 am

1 stop24h 07m

New Windsor Stewart

Wed 12/24

10:40 am-11:55 am

2 stops25h 15m

$639

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Fri 1/2

12:45 pm-10:00 am

2 stops21h 15m

New Windsor Stewart

Fri 1/9

11:09 am-2:38 pm

2 stops27h 29m

$645

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 41 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 January is currently the most expensive (average of $158). 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 21h 30m. 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 Boston Logan Intl - New Windsor Stewart, Bangor - New Windsor Stewart or Portland - 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 January is currently the most expensive (average of $158). 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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