HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$172+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SWF
May 26 — Jun 21
Tue 5/26
Tue 6/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Stewart 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 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 April 26, 2026.

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.
Thu 6/43:11 pm
PWM
-
SWF
2 stops17h 38m
Multiple Airlines
Sun 6/79:38 am
SWF
-
PWM
1 stop23h 34m
Multiple Airlines
Deal found 4/21$430
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 4/2910:57 am
PWM
-
SWF
1 stop24h 11m
Multiple Airlines
Fri 5/811:45 am
SWF
-
PWM
1 stop21h 27m
Multiple Airlines
Deal found 4/25$486
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 4/2910:57 am
PWM
-
SWF
1 stop24h 11m
Breeze Airways
Sun 5/311:48 am
SWF
-
PWM
1 stop21h 19m
Breeze Airways
Deal found 4/25$523
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.
Mon 8/179:52 am
PWM
-
SWF
1 stop25h 16m
Breeze Airways
Fri 8/2112:17 pm
SWF
-
PWM
1 stop5h 32m
Breeze Airways
Deal found 4/22$613
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
Wed 4/2910:57 am
PWM
-
SWF
1 stop24h 11m
Breeze Airways
Fri 5/17:46 pm
SWF
-
PWM
2 stops14h 31m
Breeze Airways
Deal found 4/24$629
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:51 pm
PWM
-
SWF
2 stops19h 34m
Breeze Airways
Mon 8/3112:17 pm
SWF
-
PWM
1 stop5h 32m
Breeze Airways
Deal found 4/22$633
This Gotogate deal was found by Cheapflights users on 4/25. 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.
Fri 6/53:51 pm
PWM
-
SWF
2 stops19h 34m
Breeze Airways
Sun 6/79:38 am
SWF
-
PWM
1 stop23h 34m
Breeze Airways
Deal found 4/25$636
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:51 pm
PWM
-
SWF
2 stops19h 34m
Breeze Airways
Sun 9/69:38 am
SWF
-
PWM
1 stop23h 34m
Breeze Airways
Deal found 4/22$661
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 8/2611:07 am
PWM
-
SWF
1 stop21h 51m
Breeze Airways
Fri 8/2812:17 pm
SWF
-
PWM
1 stop5h 32m
Breeze Airways
Deal found 4/21$673
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/253:16 pm
PWM
-
SWF
2 stops20h 09m
Breeze Airways
Thu 8/279:38 am
SWF
-
PWM
1 stop23h 34m
Breeze Airways
Deal found 4/21$674

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 April 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$430
(Kiwi.com)

One-way from

$172
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$258
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. 14% potential increase in price ($36 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 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 April 26, 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

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Mon 8/17

9:52 am-11:08 am

1 stop25h 16m

New Windsor Stewart

Fri 8/21

12:17 pm-5:49 pm

1 stop5h 32m

$613
Quickest round-trip

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 8/28

3:51 pm-11:25 am

2 stops19h 34m

New Windsor Stewart

Mon 8/31

12:17 pm-5:49 pm

1 stop5h 32m

$633

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 6/5

3:51 pm-11:25 am

2 stops19h 34m

New Windsor Stewart

Sun 6/7

9:38 am-9:12 am

1 stop23h 34m

$653

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 7/17

3:51 pm-11:25 am

2 stops19h 34m

New Windsor Stewart

Mon 7/20

12:17 pm-5:49 pm

1 stop5h 32m

$709

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 5/29

6:13 pm-11:25 am

3 stops17h 12m

New Windsor Stewart

Sun 5/31

9:38 am-9:12 am

1 stop23h 34m

$736

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 5/15

3:51 pm-11:25 am

2 stops19h 34m

New Windsor Stewart

Sun 5/17

9:38 am-9:12 am

1 stop23h 34m

$749

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 9/30

9:48 am-8:56 am

1 stop23h 08m

New Windsor Stewart

Sun 10/4

9:36 am-9:08 am

1 stop23h 32m

$758

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Tue 6/9

3:16 pm-11:25 am

2 stops20h 09m

New Windsor Stewart

Fri 6/12

12:17 pm-9:12 am

2 stops20h 55m

$773
Cheapest one-way

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 5/22

9:52 am-11:25 am

2 stops25h 33m

$181

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Tue 5/12

3:16 pm-11:25 am

2 stops20h 09m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

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 25h 16m. 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

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.