HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$245+ 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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SWF
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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

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 29, 2025.

Round-trip from

$507
(Mytrip)

One-way from

$245
(Mytrip)

Popular in

February

Cheapest in

September

Average price

$217
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. 17% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 July 29, 2025.

This Mytrip deal was found by Cheapflights users on 7/29. 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 8/218:52 pmPWM - SWF
2 stops19h 54mMultiple Airlines
Sun 8/246:50 pmSWF - PWM
2 stops22h 35mMultiple Airlines
Deal found 7/29$511
This Booking.com deal was found by Cheapflights users on 7/29. 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.
Wed 9/243:21 pmPWM - SWF
1 stop19h 32mBreeze Airways
Sun 9/2811:33 amSWF - PWM
1 stop21h 33mBreeze Airways
Deal found 7/29$581

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 29, 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 8/21

8:52 pm-4:46 pm

2 stops19h 54m

New Windsor Stewart

Sun 8/24

6:50 pm-5:25 pm

2 stops22h 35m

$507

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Fri 8/15

6:05 pm-6:49 pm

1 stop24h 44m

New Windsor Stewart

Sun 8/17

7:52 pm-5:25 pm

1 stop21h 33m

$647

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Thu 8/7

12:46 pm-7:06 pm

3 stops30h 20m

$245

PortlandNew Windsor

PWM - SWF

PWMSWF

Portland

Wed 9/3

3:21 pm-10:53 am

1 stop19h 32m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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 $206). 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 July 29, 2025.
Read through reviews of airlines operating flights from Portland to New Windsor, such as Breeze Airways. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
190 reviews

Crew

8.7

Overall

8.0

Food

6.7

Comfort

8.1

Entertainment

6.6

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.0
Very good
190 reviews
Breeze Airways
8.0
Very good
190 reviews

Crew

8.7

Overall

8.0

Food

6.7

Comfort

8.1

Entertainment

6.6

Boarding

8.3

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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 $206). 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

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 Portland to Stewart

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