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Stewart

$143+ Cheap flights from Portland, ME to New Windsor (PWM - SWF)

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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SWF
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Portland to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Stewart (SWF). 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

$377
(Kiwi.com)

One-way from

$143
(Kiwi.com)

Popular in

February

Cheapest in

September

Average price

$146
From Portland to New Windsor Stewart
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One-way flight from Portland to New Windsor Stewart
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Highest demand for flights based on searches. 17% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 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 Portland to Stewart

Cheapest flights from Portland to Stewart
Explore the most affordable flight options available from Portland to Stewart. 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 9/9. 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.
Wed 9/173:21 pmPWM - SWF
1 stop19h 42mBreeze Airways
Sun 9/2111:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Deal found 9/9$314
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 9/255:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Sun 9/2811:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Deal found 9/11$377
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 10/163:15 pmPWM - SWF
2 stops19h 26mMultiple Airlines
Sun 10/1911:43 amSWF - PWM
1 stop21h 23mMultiple Airlines
Deal found 9/9$383
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 9/185:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Sun 9/2111:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Deal found 9/9$481
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/243:21 pmPWM - SWF
1 stop19h 42mBreeze Airways
Sun 9/2811:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Deal found 9/9$631
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Sun 10/2611:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Deal found 9/9$665
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.
Sat 9/133:21 pmPWM - SWF
1 stop19h 42mBreeze Airways
Sun 9/2111:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Deal found 9/10$672

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Stewart 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 Portland to New Windsor that are best for you.

Fly from

Portland

Fly to

Stewart

Route

Depart

Return

Price

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Thu 9/25

5:40 pm-11:44 am

2 stops18h 04m

New Windsor Stewart

Sun 9/28

11:43 am-9:06 am

1 stop21h 23m

$377

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Thu 10/16

3:15 pm-10:41 am

2 stops19h 26m

New Windsor Stewart

Sun 10/19

11:43 am-9:06 am

1 stop21h 23m

$383

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 9/24

3:21 pm-11:03 am

1 stop19h 42m

New Windsor Stewart

Sun 9/28

11:43 am-9:06 am

1 stop21h 23m

$631

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Thu 10/23

5:40 pm-11:44 am

2 stops18h 04m

New Windsor Stewart

Sun 10/26

11:43 am-9:06 am

1 stop21h 23m

$665

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 10/1

11:26 am-11:03 am

1 stop23h 37m

New Windsor Stewart

Sun 10/5

11:43 am-9:06 am

1 stop21h 23m

$691

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 10/1

11:26 am-11:03 am

1 stop23h 37m

New Windsor Stewart

Fri 10/3

12:24 pm-10:36 am

2 stops22h 12m

$711

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 9/24

3:21 pm-11:03 am

1 stop19h 42m

New Windsor Stewart

Fri 9/26

12:24 pm-2:26 pm

2 stops26h 02m

$716

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 1/21

11:02 am-11:08 am

1 stop24h 06m

$143

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 9/20

6:18 pm-6:22 pm

1 stop24h 04m

$161

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 9/27

3:21 pm-11:03 am

1 stop19h 42m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 19 results
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Best time to book a flight from Portland to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Portland 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 Portland to New Windsor

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

Currently, October is the cheapest month in which you can book a flight from Portland, Maine to New Windsor (average of $109). Flying from Portland, Maine to New Windsor in December is currently the most expensive (average of $202). 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 Portland to Stewart. 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 Portland, Maine to New Windsor?

    Airlines like Breeze Airways fly from Portland, Maine to New Windsor in about 18h 04m. The time it takes to get you to your destination can typically vary by up to . The distance from Portland, Maine to New Windsor is about 243 mi.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Portland, Maine to New Windsor (average of $109). Flying from Portland, Maine to New Windsor in December is currently the most expensive (average of $202). 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 New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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