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Stewart

$145+ 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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SWF
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$743
(Gotogate)

One-way from

$145
(Mytrip)

Popular in

February

Cheapest in

September

Average price

$246
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.
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From Portland to New Windsor Stewart
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One-way flight from Portland to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($45 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 April 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 April 30, 2025.

This Gotogate deal was found by Cheapflights users on 4/28. 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.
Thu 6/123:17 pmPWM - SWF
2 stops21h 31mBreeze Airways
Mon 6/161:28 pmSWF - PWM
2 stops23h 37mBreeze Airways
Deal found 4/28$743

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 30, 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 6/12

3:17 pm-12:48 pm

2 stops21h 31m

New Windsor Stewart

Mon 6/16

1:28 pm-1:05 pm

2 stops23h 37m

$743

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Sun 6/8

3:30 pm-6:28 pm

2 stops26h 58m

$145

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Mon 6/30

6:05 pm-11:56 am

1 stop17h 51m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
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 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 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 $109). Flying from Portland, Maine to New Windsor in August is currently the most expensive (average of $223). 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.

Reviews of airlines servicing Stewart

Get insights into the airlines that provide service to Stewart. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Stewart. Reviews last updated April 30, 2025.
Breeze Airways
8.1
Very good
160 reviews

Entertainment

6.6

Boarding

8.3

Overall

8.1

Crew

8.8

Food

6.7

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
160 reviews
Breeze Airways
8.1
Very good
160 reviews

Entertainment

6.6

Boarding

8.3

Overall

8.1

Crew

8.8

Food

6.7

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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.

  • 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 August is currently the most expensive (average of $223). 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 Portland?

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

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