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$101+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PWM
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
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 October 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/166:16 amBOS - SWF
1 stop28h 55mMultiple Airlines
Deal found 10/15$237
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 stop20h 45mMultiple Airlines
Thu 11/205:45 amBOS - SWF
1 stop28h 37mMultiple Airlines
Deal found 10/14$239
This Mytrip deal was found by Cheapflights users on 10/16. 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 11/36:00 amBOS - SWF
1 stop11h 49mMultiple Airlines
Deal found 10/16$274
This Mytrip deal was found by Cheapflights users on 10/16. 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
Sun 11/25:00 amBOS - SWF
1 stop6h 45mMultiple Airlines
Deal found 10/16$280
This Mytrip deal was found by Cheapflights users on 10/16. 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 11/711:31 amSWF - BOS
1 stop12h 28mMultiple Airlines
Mon 11/106:00 amBOS - SWF
1 stop11h 37mMultiple Airlines
Deal found 10/16$281
This Mytrip deal was found by Cheapflights users on 10/16. 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 11/711:31 amSWF - BOS
1 stop12h 28mMultiple Airlines
Sun 11/96:00 amBOS - SWF
1 stop6h 42mMultiple Airlines
Deal found 10/16$296
This Mytrip deal was found by Cheapflights users on 10/16. 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 10/301:35 pmSWF - BOS
1 stop7h 18mMultiple Airlines
Sun 11/25:00 amBOS - SWF
1 stop6h 45mMultiple Airlines
Deal found 10/16$298
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/66:14 pmSWF - BGR
1 stop23h 56mMultiple Airlines
Mon 11/106:50 pmBGR - SWF
1 stop15h 36mMultiple Airlines
Deal found 10/15$340
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/2311:43 amSWF - PWM
1 stop21h 23mMultiple Airlines
Thu 11/273:15 pmPWM - SWF
2 stops27h 23mMultiple Airlines
Deal found 10/15$514
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/211:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Thu 11/65:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Deal found 10/16$515
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/611:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Sun 11/95:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Deal found 10/15$572
This Kiwi.com deal was found by Cheapflights users on 10/15. 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
Sat 11/296:30 pmBGR - SWF
1 stop17h 31mMultiple Airlines
Deal found 10/15$608

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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Kiwi.com)

One-way from

$101
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$189
Provider with most accurate pricing for New York (NYC)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Boston Logan Intl flights.
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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. 6% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 October 16, 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

Thu 11/13

11:43 am-8:28 am

1 stop20h 45m

Boston Logan Intl

Thu 11/20

9:57 am-10:22 am

2 stops24h 25m

$266

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 11/7

11:31 am-11:59 pm

1 stop12h 28m

Boston Logan Intl

Mon 11/10

6:00 am-5:37 pm

1 stop11h 37m

$281

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

$283

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 10/30

1:35 pm-8:53 pm

1 stop7h 18m

Boston Logan Intl

Sun 11/2

5:00 am-11:45 am

1 stop6h 45m

$299

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 10/30

1:35 pm-8:53 pm

1 stop7h 18m

Boston Logan Intl

Mon 11/3

6:00 am-5:49 pm

1 stop11h 49m

$301

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 10/30

1:35 pm-8:53 pm

1 stop7h 18m

Boston Logan Intl

Sat 11/1

9:51 pm-1:45 pm

1 stop15h 54m

$305

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 11/10

12:01 pm-11:59 pm

1 stop11h 58m

Boston Logan Intl

Fri 11/14

6:00 am-5:00 pm

1 stop11h 00m

$311

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 10/30

1:35 pm-8:53 pm

1 stop7h 18m

Boston Logan Intl

Thu 11/6

6:00 am-12:42 pm

1 stop6h 42m

$312

New WindsorBangor

SWF - BGR

SWFBGR

New Windsor Stewart

Thu 11/6

6:14 pm-6:10 pm

1 stop23h 56m

Bangor

Mon 11/10

6:50 pm-10:26 am

1 stop15h 36m

$340

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Sun 11/23

11:43 am-9:06 am

1 stop21h 23m

Portland

Thu 11/27

3:15 pm-6:38 pm

2 stops27h 23m

$514

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

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 $515, 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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