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Stewart

$157+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SWF
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
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 July 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Wed 9/211:07 am
PWM
-
SWF
1 stop22h 46m
Breeze Airways
Wed 9/3012:39 pm
SWF
-
PWM
2 stops20h 42m
Breeze Airways
Deal found 7/22$473
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Sat 12/127:12 pm
PWM
-
SWF
1 stop14h 36m
Multiple Airlines
Sun 12/2011:06 am
SWF
-
PWM
1 stop22h 02m
Multiple Airlines
Deal found 7/23$557
This FlightHub deal was found by Cheapflights users on 7/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:53 pm
PWM
-
SWF
2 stops19h 46m
Breeze Airways
Sun 10/410:56 am
SWF
-
PWM
1 stop22h 12m
Breeze Airways
Deal found 7/23$605
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Fri 8/143:51 pm
PWM
-
SWF
2 stops19h 34m
Breeze Airways
Mon 8/1712:17 pm
SWF
-
PWM
1 stop5h 32m
Breeze Airways
Deal found 7/26$615
This Booking.com deal was found by Cheapflights users on 7/25. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:53 pm
PWM
-
SWF
2 stops19h 46m
Breeze Airways
Sun 9/2710:56 am
SWF
-
PWM
1 stop22h 12m
Breeze Airways
Deal found 7/25$624
This Booking.com deal was found by Cheapflights users on 7/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:53 pm
PWM
-
SWF
2 stops19h 46m
Breeze Airways
Sun 9/2010:56 am
SWF
-
PWM
1 stop22h 12m
Breeze Airways
Deal found 7/23$644
This KAYAK deal was found by Cheapflights users on 7/23. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:09 pm
PWM
-
SWF
1 stop18h 30m
Breeze Airways
Thu 10/1510:56 am
SWF
-
PWM
1 stop22h 12m
Breeze Airways
Deal found 7/23$648
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Sat 8/2211:07 am
PWM
-
SWF
1 stop22h 46m
Breeze Airways
Sat 8/2912:05 pm
SWF
-
PWM
2 stops34h 34m
Breeze Airways
Deal found 7/23$649
This FlightHub deal was found by Cheapflights users on 7/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:53 pm
PWM
-
SWF
2 stops19h 46m
Breeze Airways
Sun 9/1310:56 am
SWF
-
PWM
1 stop22h 12m
Breeze Airways
Deal found 7/25$655
This Booking.com deal was found by Cheapflights users on 7/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:09 pm
PWM
-
SWF
1 stop18h 30m
Breeze Airways
Thu 9/1710:56 am
SWF
-
PWM
1 stop22h 12m
Breeze Airways
Deal found 7/26$658

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 July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$473
(Kiwi.com)

One-way from

$157
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$250
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. 10% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 27, 2026.
Use the filters below to find and compare flights from Portland to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 8/14

3:51 pm-11:25 am

2 stops19h 34m

New Windsor Stewart

Mon 8/17

12:17 pm-5:49 pm

1 stop5h 32m

$615

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 9/11

3:53 pm-11:39 am

2 stops19h 46m

New Windsor Stewart

Sun 9/13

10:56 am-9:08 am

1 stop22h 12m

$644

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 9/18

3:53 pm-11:39 am

2 stops19h 46m

New Windsor Stewart

Sun 9/20

10:56 am-9:08 am

1 stop22h 12m

$644

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Mon 8/24

9:52 am-11:08 am

1 stop25h 16m

New Windsor Stewart

Mon 8/31

11:10 am-5:49 pm

1 stop6h 39m

$743

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 9/9

11:08 am-10:16 am

1 stop23h 08m

New Windsor Stewart

Wed 9/16

12:39 pm-9:19 pm

2 stops8h 40m

$763

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 8/26

11:07 am-9:53 am

1 stop22h 46m

New Windsor Stewart

Fri 8/28

12:17 pm-5:49 pm

1 stop5h 32m

$768

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 8/7

3:51 pm-11:25 am

2 stops19h 34m

New Windsor Stewart

Tue 8/11

11:48 am-10:27 am

1 stop22h 39m

$774

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 8/21

3:51 pm-11:25 am

2 stops19h 34m

New Windsor Stewart

Mon 8/24

12:17 pm-5:49 pm

1 stop5h 32m

$789
Cheapest one-way

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Tue 9/1

8:00 am-11:25 am

3 stops27h 25m

$207
Quickest one-way

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 9/25

5:30 pm-11:39 am

3 stops18h 09m

$214

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 19 resultsSorted by cheapest first
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.

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 19h 34m. 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.

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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