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Stewart

$199+ 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 3/28. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SWF
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap 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 January 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. 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 5/305:01 pm
PWM
-
SWF
2 stops15h 57m
Breeze Airways
Sun 6/79:38 am
SWF
-
PWM
1 stop23h 34m
Breeze Airways
Deal found 1/26$415
This Booking.com deal was found by Cheapflights users on 1/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/303:16 pm
PWM
-
SWF
2 stops20h 09m
Breeze Airways
Thu 7/29:38 am
SWF
-
PWM
1 stop23h 34m
Breeze Airways
Deal found 1/24$606
This Gotogate deal was found by Cheapflights users on 1/24. 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 5/83:51 pm
PWM
-
SWF
2 stops19h 34m
Breeze Airways
Sun 5/109:38 am
SWF
-
PWM
1 stop23h 34m
Breeze Airways
Deal found 1/24$670
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 1/316:18 pm
PWM
-
SWF
1 stop15h 40m
Multiple Airlines
Sun 2/112:13 pm
SWF
-
PWM
1 stop20h 54m
Multiple Airlines
Deal found 1/24$869
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 3/710:57 am
PWM
-
SWF
1 stop23h 11m
Breeze Airways
Sun 3/1511:48 am
SWF
-
PWM
1 stop21h 19m
Breeze Airways
Deal found 1/24$882
This Gotogate deal was found by Cheapflights users on 1/26. 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.
Wed 3/2510:57 am
PWM
-
SWF
1 stop24h 11m
Breeze Airways
Sun 3/2911:48 am
SWF
-
PWM
1 stop21h 19m
Breeze Airways
Deal found 1/26$890
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 1/2811:02 am
PWM
-
SWF
1 stop24h 31m
Breeze Airways
Fri 1/3012:11 pm
SWF
-
PWM
2 stops22h 11m
Breeze Airways
Deal found 1/25$975
This Gotogate deal was found by Cheapflights users on 1/25. 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.
Wed 2/1110:57 am
PWM
-
SWF
1 stop24h 11m
Breeze Airways
Sun 2/1511:48 am
SWF
-
PWM
1 stop21h 19m
Breeze Airways
Deal found 1/25$1,018

Find 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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$415
(Kiwi.com)

One-way from

$199
(Kiwi.com)

Popular in

November

Cheapest in

May

Average price

$238
Provider with most accurate pricing for Portland-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-New Windsor Stewart flights.
Search Deals
From Portland to New Windsor Stewart
Search Deals
One-way flight from Portland to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($4 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 January 2026
Search Deals

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 January 26, 2026.
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

Sat 5/30

5:01 pm-8:58 am

2 stops15h 57m

New Windsor Stewart

Sun 6/7

9:38 am-9:12 am

1 stop23h 34m

$415

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 3/25

10:57 am-11:08 am

1 stop24h 11m

New Windsor Stewart

Fri 3/27

12:11 pm-10:17 am

2 stops22h 06m

$747

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 3/11

10:57 am-11:08 am

1 stop24h 11m

New Windsor Stewart

Sun 3/15

11:48 am-9:07 am

1 stop21h 19m

$814

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 3/7

10:57 am-10:08 am

1 stop23h 11m

New Windsor Stewart

Sun 3/15

11:48 am-9:07 am

1 stop21h 19m

$882

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 3/25

10:57 am-11:08 am

1 stop24h 11m

New Windsor Stewart

Sun 3/29

11:48 am-9:07 am

1 stop21h 19m

$890

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 2/11

10:57 am-11:08 am

1 stop24h 11m

New Windsor Stewart

Sun 2/15

11:48 am-9:07 am

1 stop21h 19m

$1,018

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 3/28

10:57 am-9:39 am

2 stops22h 42m

$199

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 3/13

5:06 pm-11:39 am

2 stops42h 33m

$304

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 2/6

5:06 pm-11:08 am

3 stops42h 02m

$307

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sun 3/22

6:19 pm-7:01 pm

3 stops24h 42m

$356

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 13 results
1
2
  • Most accurate provider: When it comes to deals on Portland, Maine-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-New Windsor 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 Portland, Maine-New Windsor 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 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, August is the cheapest month in which you can book a flight from Portland, Maine to New Windsor (average of $57). Flying from Portland, Maine to New Windsor in April is currently the most expensive (average of $109). 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 15h 57m. 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, August is the cheapest month in which you can book a flight from Portland, Maine to New Windsor (average of $57). Flying from Portland, Maine to New Windsor in April is currently the most expensive (average of $109). 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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