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$145+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PWM
Jul 12 — Jul 191
Sun 7/12
Sun 7/19
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 June 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/7. 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 10/1512:14 pm
SWF
-
PWM
2 stops10h 05m
Multiple Airlines
Tue 10/275:09 pm
PWM
-
SWF
1 stop18h 30m
Multiple Airlines
Deal found 6/7$449
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 10/1510:56 am
SWF
-
PWM
1 stop22h 12m
Breeze Airways
Tue 10/275:09 pm
PWM
-
SWF
1 stop18h 30m
Breeze Airways
Deal found 6/7$452
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 9/1010:56 am
SWF
-
PWM
1 stop22h 12m
Multiple Airlines
Sun 9/137:00 am
PWM
-
SWF
2 stops10h 31m
Multiple Airlines
Deal found 6/10$457
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 9/2510:48 am
SWF
-
PWM
1 stop6h 02m
Multiple Airlines
Sun 9/277:00 am
PWM
-
SWF
2 stops10h 31m
Multiple Airlines
Deal found 6/7$495
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Sun 7/1910:28 am
SWF
-
PWM
2 stops12h 11m
Multiple Airlines
Sat 7/2511:07 am
PWM
-
SWF
1 stop22h 46m
Multiple Airlines
Deal found 6/10$589
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Wed 9/1612:39 pm
SWF
-
PWM
2 stops8h 40m
Multiple Airlines
Wed 9/236:31 pm
PWM
-
SWF
1 stop15h 52m
Multiple Airlines
Deal found 6/11$592
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Sun 7/1910:33 am
SWF
-
PWM
1 stop22h 39m
Breeze Airways
Sat 7/2511:07 am
PWM
-
SWF
1 stop22h 46m
Breeze Airways
Deal found 6/10$600
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 6/2311:48 am
SWF
-
PWM
1 stop22h 39m
Breeze Airways
Fri 6/263:51 pm
PWM
-
SWF
2 stops19h 34m
Breeze Airways
Deal found 6/9$636
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 8/1310:28 am
SWF
-
PWM
2 stops12h 11m
Multiple Airlines
Sat 8/156:38 pm
PWM
-
SWF
1 stop16h 17m
Multiple Airlines
Deal found 6/10$646
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Thu 7/2310:28 am
SWF
-
PWM
2 stops12h 11m
Multiple Airlines
Sat 7/256:38 pm
PWM
-
SWF
1 stop16h 17m
Multiple Airlines
Deal found 6/9$671
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Thu 7/210:28 am
SWF
-
PWM
2 stops12h 11m
Multiple Airlines
Mon 7/69:52 am
PWM
-
SWF
1 stop25h 16m
Multiple Airlines
Deal found 6/11$684

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 June 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$449
(Kiwi.com)

One-way from

$145
(Kiwi.com)

Popular in

March

Cheapest in

May

Average price

$278
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. 7% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 June 12, 2026.
Use the filters below to find and compare flights from New Windsor to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 8/6

10:33 am-9:12 am

1 stop22h 39m

Portland

Mon 8/10

9:52 am-11:08 am

1 stop25h 16m

$708

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 9/3

10:33 am-9:12 am

1 stop22h 39m

Portland

Tue 9/8

3:16 pm-11:39 am

2 stops20h 23m

$764

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Mon 8/31

11:10 am-5:49 pm

1 stop6h 39m

Portland

Sat 9/5

11:07 am-9:53 am

1 stop22h 46m

$788

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 7/23

10:33 am-9:12 am

1 stop22h 39m

Portland

Tue 7/28

3:16 pm-11:25 am

2 stops20h 09m

$824

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Mon 7/6

12:17 pm-5:49 pm

1 stop5h 32m

Portland

Fri 7/10

3:51 pm-11:25 am

2 stops19h 34m

$853
Quickest round-trip

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 7/3

12:17 pm-5:49 pm

1 stop5h 32m

Portland

Sun 7/5

7:00 am-5:40 pm

2 stops10h 40m

$863

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 7/3

12:17 pm-10:27 am

2 stops22h 10m

Portland

Wed 7/8

11:07 am-9:53 am

1 stop22h 46m

$864

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 7/17

12:17 pm-10:27 am

2 stops22h 10m

Portland

Mon 7/20

9:52 am-11:08 am

1 stop25h 16m

$874

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Mon 8/10

12:17 pm-5:49 pm

1 stop5h 32m

Portland

Fri 8/14

6:29 pm-11:25 am

3 stops16h 56m

$889

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Sun 8/30

10:33 am-9:12 am

1 stop22h 39m

Portland

Thu 9/3

3:11 pm-11:37 am

2 stops20h 26m

$918

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

Showing 1-10 of 23 resultsSorted by cheapest first
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3

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 June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 FlightHub the most. FlightHub 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.

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 22h 39m. 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.

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
Lewiston
Conway

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