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Stewart

$170+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SWF
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$324
(Kiwi.com)

One-way from

$170
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$196
Provider with most accurate pricing for Portland-New Windsor Stewart flight deals.
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Provider most trusted by Cheapflights users for Portland-New Windsor Stewart flights.
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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. 14% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/36:18 pmPWM - SWF
1 stop16h 01mMultiple Airlines
Sun 12/711:43 amSWF - PWM
1 stop21h 23mMultiple Airlines
Deal found 10/27$324
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Thu 11/135:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Sun 11/1611:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Deal found 10/26$498
This Gotogate deal was found by Cheapflights users on 10/28. 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 11/1211:16 amPWM - SWF
1 stop23h 47mBreeze Airways
Sun 11/1611:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Deal found 10/28$608
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 10/305:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Sun 11/211:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Deal found 10/28$631
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/811:16 amPWM - SWF
1 stop23h 47mMultiple Airlines
Thu 11/136:14 pmSWF - PWM
2 stops23h 11mMultiple Airlines
Deal found 10/27$642
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/1211:16 amPWM - SWF
1 stop23h 47mMultiple Airlines
Thu 11/136:14 pmSWF - PWM
2 stops23h 11mMultiple Airlines
Deal found 10/27$650
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Thu 11/205:40 pmPWM - SWF
2 stops18h 04mBreeze Airways
Sun 11/2311:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Deal found 10/26$669
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Sat 11/111:16 amPWM - SWF
1 stop24h 47mMultiple Airlines
Sun 11/26:16 pmSWF - PWM
2 stops23h 09mMultiple Airlines
Deal found 10/25$722
This Gotogate deal was found by Cheapflights users on 10/27. 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.
Sat 11/811:16 amPWM - SWF
1 stop23h 47mBreeze Airways
Thu 11/1311:43 amSWF - PWM
1 stop21h 23mBreeze Airways
Deal found 10/27$761
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/2011:16 amPWM - SWF
1 stop23h 47mBreeze Airways
Tue 12/2311:43 amSWF - PWM
1 stop22h 53mBreeze Airways
Deal found 10/27$778

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 October 28, 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 11/13

5:40 pm-11:44 am

2 stops18h 04m

New Windsor Stewart

Sun 11/16

11:43 am-9:06 am

1 stop21h 23m

$498

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 11/12

11:16 am-11:03 am

1 stop23h 47m

New Windsor Stewart

Sun 11/16

11:43 am-9:06 am

1 stop21h 23m

$609

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 4/8

11:02 am-11:08 am

1 stop24h 06m

New Windsor Stewart

Thu 4/16

11:48 am-9:07 am

1 stop21h 19m

$634

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 11/8

11:16 am-11:03 am

1 stop23h 47m

New Windsor Stewart

Thu 11/13

6:14 pm-5:25 pm

2 stops23h 11m

$642

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 11/12

11:16 am-11:03 am

1 stop23h 47m

New Windsor Stewart

Thu 11/13

6:14 pm-5:25 pm

2 stops23h 11m

$650

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Thu 11/20

5:40 pm-11:44 am

2 stops18h 04m

New Windsor Stewart

Sun 11/23

11:43 am-9:06 am

1 stop21h 23m

$669

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 11/8

11:16 am-11:03 am

1 stop23h 47m

New Windsor Stewart

Thu 11/13

11:43 am-9:06 am

1 stop21h 23m

$761

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 4/11

11:02 am-11:08 am

1 stop24h 06m

New Windsor Stewart

Thu 4/16

11:48 am-9:07 am

1 stop21h 19m

$768

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sat 12/20

11:16 am-11:03 am

1 stop23h 47m

New Windsor Stewart

Tue 12/23

11:43 am-10:36 am

1 stop22h 53m

$778

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 4/15

11:02 am-11:08 am

1 stop24h 06m

New Windsor Stewart

Thu 4/23

11:48 am-9:07 am

1 stop21h 19m

$841

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 20 results
1
2

Compare providers for flights from Portland to Stewart

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Stewart in October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Portland, Maine-New Windsor flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland, Maine-New Windsor flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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, October is the cheapest month in which you can book a flight from Portland, Maine to New Windsor (average of $55). Flying from Portland, Maine to New Windsor in February is currently the most expensive (average of $117). 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 $55). Flying from Portland, Maine to New Windsor in February is currently the most expensive (average of $117). 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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