HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$146+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PWM
May 24 — May 311
Sun 5/24
Sun 5/31
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Portland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 24, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/22. 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 8/279:38 am
SWF
-
PWM
1 stop23h 34m
Breeze Airways
Tue 9/13:16 pm
PWM
-
SWF
2 stops20h 09m
Breeze Airways
Deal found 4/22$370
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 9/3012:39 pm
SWF
-
PWM
2 stops20h 42m
Breeze Airways
Tue 10/65:09 pm
PWM
-
SWF
1 stop18h 30m
Breeze Airways
Deal found 4/21$403
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/811:45 am
SWF
-
PWM
1 stop21h 27m
Multiple Airlines
Tue 5/123:16 pm
PWM
-
SWF
2 stops20h 09m
Multiple Airlines
Deal found 4/20$413
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/79:38 am
SWF
-
PWM
1 stop23h 34m
Breeze Airways
Tue 5/123:16 pm
PWM
-
SWF
2 stops20h 09m
Breeze Airways
Deal found 4/20$439
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 10/99:40 am
SWF
-
PWM
1 stop23h 28m
Multiple Airlines
Tue 10/135:09 pm
PWM
-
SWF
1 stop18h 30m
Multiple Airlines
Deal found 4/20$448
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/229:41 am
SWF
-
PWM
1 stop23h 31m
Multiple Airlines
Tue 5/263:16 pm
PWM
-
SWF
2 stops20h 09m
Multiple Airlines
Deal found 4/23$466
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 5/149:38 am
SWF
-
PWM
1 stop23h 34m
Breeze Airways
Tue 5/193:16 pm
PWM
-
SWF
2 stops20h 09m
Breeze Airways
Deal found 4/22$470
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 5/79:38 am
SWF
-
PWM
1 stop23h 34m
Breeze Airways
Mon 5/113:51 pm
PWM
-
SWF
2 stops43h 34m
Breeze Airways
Deal found 4/22$475
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 8/1610:28 am
SWF
-
PWM
2 stops12h 11m
Multiple Airlines
Sat 8/229:52 am
PWM
-
SWF
1 stop23h 06m
Multiple Airlines
Deal found 4/21$480
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 8/610:28 am
SWF
-
PWM
2 stops12h 11m
Multiple Airlines
Mon 8/179:52 am
PWM
-
SWF
1 stop25h 16m
Multiple Airlines
Deal found 4/23$501
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 8/156:50 pm
SWF
-
PWM
2 stops27h 49m
Multiple Airlines
Sat 8/226:38 pm
PWM
-
SWF
1 stop15h 49m
Multiple Airlines
Deal found 4/19$511
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 7/199:38 am
SWF
-
PWM
1 stop23h 34m
Breeze Airways
Fri 7/243:51 pm
PWM
-
SWF
2 stops19h 34m
Breeze Airways
Deal found 4/22$514

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 April 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$370
(Kiwi.com)

One-way from

$146
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$238
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. 8% potential increase in price ($23 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 April 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 April 24, 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

Sun 7/12

9:38 am-9:12 am

1 stop23h 34m

Portland

Thu 7/16

7:00 am-5:40 pm

2 stops10h 40m

$521

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 5/22

9:41 am-9:12 am

1 stop23h 31m

Portland

Tue 5/26

3:16 pm-11:25 am

2 stops20h 09m

$535

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 5/7

9:38 am-9:12 am

1 stop23h 34m

Portland

Sun 5/10

3:11 pm-10:55 am

2 stops19h 44m

$538

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Sat 7/11

6:44 pm-2:26 pm

2 stops19h 42m

Portland

Wed 7/15

11:07 am-8:58 am

1 stop21h 51m

$538

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 6/11

9:38 am-9:12 am

1 stop23h 34m

Portland

Wed 6/17

5:01 pm-8:58 am

2 stops15h 57m

$678

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Sun 5/31

9:38 am-9:12 am

1 stop23h 34m

Portland

Sat 6/6

9:52 am-8:58 am

1 stop23h 06m

$728

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Sun 6/14

9:38 am-9:12 am

1 stop23h 34m

Portland

Fri 6/19

3:51 pm-11:25 am

2 stops19h 34m

$744

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 5/28

9:38 am-9:12 am

1 stop23h 34m

Portland

Wed 6/10

11:07 am-8:58 am

1 stop21h 51m

$748

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Sun 6/21

9:38 am-9:12 am

1 stop23h 34m

Portland

Sat 6/27

6:26 pm-7:14 pm

1 stop24h 48m

$786

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 7/9

9:38 am-9:12 am

1 stop23h 34m

Portland

Tue 7/14

3:16 pm-11:25 am

2 stops20h 09m

$809

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/19

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
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 April.
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 23h 34m. 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
Auburn
Lewiston
Conway

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights