HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$280+ Cheap flights from New Windsor to Portland, ME (SWF - PWM)

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 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PWM
Apr 27 — May 41
Sun 4/27
Sun 5/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Portland 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 Stewart to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Portland (PWM). 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 22, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$547
(Mytrip)

One-way from

$280
(Gotogate)

Popular in

December

Cheapest in

August

Average price

$211
Provider with most accurate pricing for New Windsor Stewart-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Portland flights.
Search Deals
From New Windsor Stewart to Portland
Search Deals
One-way flight from New Windsor Stewart to Portland
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($38 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 April 2025
Search Deals

Find flight deals from Stewart to Portland

Cheapest flights from Stewart to Portland
Explore the most affordable flight options available from Stewart to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/57:06 pmSWF - PWM
2 stops23h 32mMultiple Airlines
Sun 6/83:30 pmPWM - SWF
2 stops26h 58mMultiple Airlines
Deal found 4/21$547
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1212:24 pmSWF - PWM
2 stops26h 12mBreeze Airways
Wed 9/173:38 pmPWM - SWF
1 stop19h 15mBreeze Airways
Deal found 4/21$580

Cheapflights Fare Finder

Customize your flight search to find flights from Stewart to Portland 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 22, 2025.
Use the filters below to find and compare flights from New Windsor to Portland that are best for you.

Fly from

Stewart

Fly to

Portland

Route

Depart

Return

Price

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 6/5

7:06 pm-6:38 pm

2 stops23h 32m

Portland

Sun 6/8

3:30 pm-6:28 pm

2 stops26h 58m

$547

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Thu 7/10

7:52 pm-5:25 pm

1 stop21h 33m

Portland

Mon 7/14

6:05 pm-11:56 am

1 stop17h 51m

$636

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Sun 6/15

7:52 pm-6:38 pm

1 stop22h 46m

$280

New WindsorPortland

SWF - PWM

SWFPWM

New Windsor Stewart

Fri 5/9

11:50 am-9:43 am

2 stops21h 53m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Compare providers for flights from Stewart to Portland

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 Stewart to Portland in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 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 New Windsor-Portland, Maine flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on New Windsor-Portland, Maine flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from New Windsor-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Portland, Maine 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 New Windsor-Portland, Maine 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 Stewart to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Stewart 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 New Windsor to Portland

What is the cheapest month to book a flight from New Windsor to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from New Windsor to Portland, Maine (average of $296). Flying from New Windsor to Portland, Maine in May is currently the most expensive (average of $416). 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.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated April 22, 2025.
Breeze Airways
8.1
Very good
158 reviews

Entertainment

6.6

Food

6.7

Crew

8.8

Overall

8.1

Comfort

8.2

Boarding

8.3

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
158 reviews
Breeze Airways
8.1
Very good
158 reviews

Entertainment

6.6

Food

6.7

Crew

8.8

Overall

8.1

Comfort

8.2

Boarding

8.3

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 Stewart to Portland. 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 Stewart to Portland that include hotel bookings?

    Yes. In addition to deals on Stewart to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Portland.

  • Can I find deals for business class flights from Stewart to Portland?

    Yes. Cheapflights offers flight deals from Stewart to Portland 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 New Windsor to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Portland, Maine (average of $296). Flying from New Windsor to Portland, Maine in May is currently the most expensive (average of $416). 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
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

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.

Alternative routes for Stewart to Portland

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Boston flights
LaGuardia to Boston flights
John F Kennedy Intl to Boston flights
LaGuardia to Portland flights
John F Kennedy Intl to Portland flights
Newark to Portland flights
Newark to Bangor flights
Buffalo to Boston flights
LaGuardia to Bangor flights
John F Kennedy Intl to Bangor flights
White Plains to Boston flights
Rochester to Boston flights
Syracuse to Boston flights
Islip to Boston flights
Stewart to Boston flights
Buffalo to Portland flights
John F Kennedy Intl to Bar Harbor flights
White Plains to Portland flights
Newark to Bar Harbor flights
Rochester to Portland flights
Rochester to Bangor flights
Stewart to Bangor flights
Buffalo to Bangor flights
Ithaca to Boston flights
Albany to Portland flights
Binghamton to Boston flights
John F Kennedy Intl to Augusta flights
Islip to Portland flights
Syracuse to Portland flights
Albany to Boston flights
Elmira to Boston flights
Syracuse to Bangor flights
Newark to Augusta flights
John F Kennedy Intl to Rockland flights
Albany to Bangor flights
Saranac Lake to Boston flights
LaGuardia to Augusta flights
Ithaca to Portland flights
LaGuardia to Bar Harbor flights
Newark to Rockland flights
White Plains to Bangor flights
Rutland to Boston flights
Buffalo to Rockland flights
Ithaca to Bangor flights
Niagara Falls to Boston flights
White Plains to Augusta flights
Elmira to Portland flights
Binghamton to Portland flights
White Plains to Bar Harbor flights

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.