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$156+ Cheap flights from New Windsor to Portland, ME (SWF - PWM)

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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PWM
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Stewart to Portland

Cheapest flights from Stewart to Portland
Explore the most affordable flight options available from Stewart to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/8. 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
Wed 12/246:18 pmPWM - SWF
2 stops40h 49mMultiple Airlines
Deal found 12/8$553
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 12/3011:43 amSWF - PWM
1 stop22h 53mBreeze Airways
Sat 1/311:16 amPWM - SWF
1 stop23h 47mBreeze Airways
Deal found 12/9$771
This Kiwi.com deal was found by Cheapflights users on 12/11. 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
Wed 12/3111:16 amPWM - SWF
1 stop23h 47mMultiple Airlines
Deal found 12/11$774
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 - PWM
1 stop21h 23mBreeze Airways
Mon 12/299:46 amPWM - SWF
1 stop25h 17mBreeze Airways
Deal found 12/10$794
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 - PWM
1 stop21h 23mBreeze Airways
Wed 12/3111:16 amPWM - SWF
1 stop23h 47mBreeze Airways
Deal found 12/11$812
This Gotogate deal was found by Cheapflights users on 12/11. 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.
Fri 12/1912:24 pmSWF - PWM
2 stops22h 12mBreeze Airways
Wed 12/3111:16 amPWM - SWF
1 stop23h 47mBreeze Airways
Deal found 12/11$844
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/1912:24 pmSWF - PWM
2 stops22h 12mBreeze Airways
Mon 12/299:46 amPWM - SWF
1 stop25h 17mBreeze Airways
Deal found 12/10$853
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 - PWM
1 stop15h 06mMultiple Airlines
Sat 12/136:18 pmPWM - SWF
1 stop16h 01mMultiple Airlines
Deal found 12/11$854
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 - PWM
1 stop21h 23mMultiple Airlines
Sat 12/276:18 pmPWM - SWF
1 stop15h 41mMultiple Airlines
Deal found 12/10$1,001

Find flight deals from Stewart to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Portland (PWM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$658
(Booking.com)

One-way from

$156
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$223
Provider with most accurate pricing for New Windsor Stewart-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Portland flights.
Search Deals
From New Windsor Stewart to Portland
Search Deals
One-way flight from New Windsor Stewart to Portland
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 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 Portland 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 12, 2025.
Use the filters below to find and compare flights from New Windsor to Portland that are best for you.

Fly from

Stewart

Fly to

Portland

Route

Depart

Return

Price

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 12/19

8:11 pm-10:36 am

1 stop14h 25m

Portland

Wed 12/24

6:18 pm-11:07 am

2 stops40h 49m

$553

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 1/8

12:13 pm-9:07 am

1 stop20h 54m

Portland

Sat 1/10

11:02 am-11:33 am

1 stop24h 31m

$658

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Tue 12/30

11:43 am-10:36 am

1 stop22h 53m

Portland

Sat 1/3

11:16 am-11:03 am

1 stop23h 47m

$771

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 12/19

8:11 pm-10:36 am

1 stop14h 25m

Portland

Wed 12/31

11:16 am-11:03 am

1 stop23h 47m

$774

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 12/18

11:43 am-9:06 am

1 stop21h 23m

Portland

Mon 12/29

9:46 am-11:03 am

1 stop25h 17m

$794

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Sun 12/21

11:43 am-9:06 am

1 stop21h 23m

Portland

Wed 12/31

11:16 am-11:03 am

1 stop23h 47m

$812

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 12/19

12:24 pm-10:36 am

2 stops22h 12m

Portland

Wed 12/31

11:16 am-11:03 am

1 stop23h 47m

$844

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 12/19

12:24 pm-10:36 am

2 stops22h 12m

Portland

Mon 12/29

9:46 am-11:03 am

1 stop25h 17m

$853

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 12/18

11:43 am-9:06 am

1 stop21h 23m

Portland

Sat 12/27

6:18 pm-9:59 am

1 stop15h 41m

$1,001

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 2/6

7:33 pm-10:17 am

1 stop14h 44m

$156

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 18 results
1
2

Compare providers for flights from Stewart to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart to Portland in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New Windsor-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Portland, Maine flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Windsor-Portland, Maine flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Stewart to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland 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 Portland

What is the cheapest month to book a flight from New Windsor to Portland, Maine?

Currently, April is the cheapest month in which you can book a flight from New Windsor to Portland, Maine (average of $58). Flying from New Windsor to Portland, Maine in February is currently the most expensive (average of $165). 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 Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from New Windsor to Portland, Maine?

    Airlines like Breeze Airways fly from New Windsor to Portland, Maine in about 20h 54m. The time it takes to get you to your destination can typically vary by up to . New Windsor and Portland, Maine are separated by a distance of 243 mi.

  • Can I find deals for flights from Stewart to Portland that include hotel bookings?

    Yes. In addition to deals on Stewart to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Portland.

  • Can I find deals for business class flights from Stewart to Portland?

    Yes. Cheapflights offers flight deals from Stewart to Portland 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 Portland, Maine?

    Currently, April is the cheapest month in which you can book a flight from New Windsor to Portland, Maine (average of $58). Flying from New Windsor to Portland, Maine in February is currently the most expensive (average of $165). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Brunswick
Auburn
Conway

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