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$177+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PWM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$623
(Gotogate)

One-way from

$177
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$182
From New Windsor Stewart to Portland
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One-way flight from New Windsor Stewart to Portland
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Highest demand for flights based on searches. 14% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/1811:43 amSWF - PWM
1 stop21h 23mMultiple Airlines
Sat 9/206:18 pmPWM - SWF
1 stop24h 04mMultiple Airlines
Deal found 9/11$393
This Gotogate deal was found by Cheapflights users on 9/11. 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.
Thu 12/411:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Sat 12/611:16 amPWM - SWF
1 stop23h 47mBreeze Airways
Deal found 9/11$623
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/2311:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Sun 10/265:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Deal found 9/11$650
This KAYAK deal was found by Cheapflights users on 9/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2111:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Wed 9/243:21 pmPWM - SWF
1 stop19h 42mBreeze Airways
Deal found 9/10$680
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/211:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Sun 10/55:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Deal found 9/9$683
This Gotogate deal was found by Cheapflights users on 9/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2412:24 pmSWF - PWM
2 stops22h 12mBreeze Airways
Sun 10/265:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Deal found 9/10$709
This Gotogate deal was found by Cheapflights users on 9/11. 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 10/312:24 pmSWF - PWM
2 stops22h 12mBreeze Airways
Wed 10/811:16 amPWM - SWF
1 stop23h 47mBreeze Airways
Deal found 9/11$718
This KAYAK deal was found by Cheapflights users on 9/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1111:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Wed 9/173:21 pmPWM - SWF
1 stop19h 42mBreeze Airways
Deal found 9/10$728
This Gotogate deal was found by Cheapflights users on 9/11. 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.
Thu 11/1311:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Sun 11/165:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Deal found 9/11$731
This FlightHub deal was found by Cheapflights users on 9/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:24 pmSWF - PWM
2 stops22h 12mBreeze Airways
Sat 10/1111:16 amPWM - SWF
1 stop23h 47mBreeze Airways
Deal found 9/11$739
This Justfly.com deal was found by Cheapflights users on 9/11. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1811:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Sat 9/203:21 pmPWM - SWF
1 stop19h 42mBreeze Airways
Deal found 9/11$745

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 September 11, 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

Thu 12/4

11:43 am-9:06 am

1 stop21h 23m

Portland

Sat 12/6

11:16 am-11:03 am

1 stop23h 47m

$623

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 10/23

11:43 am-9:06 am

1 stop21h 23m

Portland

Sun 10/26

5:40 pm-11:44 am

2 stops18h 04m

$650

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Sun 9/21

11:43 am-9:06 am

1 stop21h 23m

Portland

Wed 9/24

3:21 pm-11:03 am

1 stop19h 42m

$680

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 10/2

11:43 am-9:06 am

1 stop21h 23m

Portland

Sun 10/5

5:40 pm-11:44 am

2 stops18h 04m

$683

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 10/31

12:24 pm-10:36 am

2 stops22h 12m

Portland

Sun 11/2

5:40 pm-11:44 am

2 stops18h 04m

$683

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 10/24

12:24 pm-10:36 am

2 stops22h 12m

Portland

Sun 10/26

5:40 pm-11:44 am

2 stops18h 04m

$709

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 10/3

12:24 pm-10:36 am

2 stops22h 12m

Portland

Sat 10/11

11:16 am-11:03 am

1 stop23h 47m

$739

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 11/7

12:24 pm-10:36 am

2 stops22h 12m

Portland

Sun 11/9

5:40 pm-11:44 am

2 stops18h 04m

$748

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 10/3

12:24 pm-10:36 am

2 stops22h 12m

Portland

Sun 10/5

5:40 pm-11:44 am

2 stops18h 04m

$757

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 10/23

11:43 am-9:06 am

1 stop21h 23m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 19 results
1
2

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, January is the cheapest month in which you can book a flight from New Windsor to Portland, Maine (average of $296). Flying from New Windsor to Portland, Maine in July is currently the most expensive (average of $394). 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 21h 23m. 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, January is the cheapest month in which you can book a flight from New Windsor to Portland, Maine (average of $296). Flying from New Windsor to Portland, Maine in July is currently the most expensive (average of $394). 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
Brunswick
North Conway
Auburn
Conway
Lewiston

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