HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$146+ Cheap flights from Portland to New Windsor (PDX - 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SWF
feb. 20 — feb. 271
vie. 2/20
vie. 2/27
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

One-way flights from Portland to Stewart
Search for one-way flight options from Portland to Stewart. Find affordable one-way fares based on user searches. Data last updated enero 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
lun. 2/99:22 pm
PDX
-
SWF
2 stops40h 34m
Multiple Airlines
Deal found 1/21$146
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
lun. 3/210:18 pm
PDX
-
SWF
3 stops56h 01m
Multiple Airlines
Deal found 1/20$177
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
lun. 2/2310:18 pm
PDX
-
SWF
3 stops57h 44m
Multiple Airlines
Deal found 1/20$207
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
sáb. 3/1410:24 am
PDX
-
SWF
2 stops43h 38m
Multiple Airlines
Deal found 1/20$221
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
lun. 3/169:53 pm
PDX
-
SWF
3 stops56h 46m
Multiple Airlines
Deal found 1/20$231
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
vie. 3/612:04 pm
PDX
-
SWF
3 stops41h 15m
Multiple Airlines
Deal found 1/21$256
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
mié. 3/119:53 am
PDX
-
SWF
3 stops44h 09m
Multiple Airlines
Deal found 1/21$279
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
vie. 1/309:22 pm
PDX
-
SWF
3 stops57h 57m
Multiple Airlines
Deal found 1/19$284

Find flight deals from Portland to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) 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 enero 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Popular in

December

Cheapest in

February

Average price

$344
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
Highest demand for flights based on searches. 9% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 enero 21, 2026.
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

PDX - SWF

PDXSWF

Portland

lun. 2/9

9:22 pm-4:56 pm

2 stops40h 34m

$146

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

lun. 3/2

10:18 pm-9:19 am

3 stops56h 01m

$177

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

lun. 2/23

10:18 pm-11:02 am

3 stops57h 44m

$207

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

sáb. 3/14

10:24 am-9:02 am

2 stops43h 38m

$221

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

lun. 3/16

9:53 pm-9:39 am

3 stops56h 46m

$231

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

vie. 3/6

12:04 pm-8:19 am

3 stops41h 15m

$256

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

vie. 1/30

9:22 pm-10:19 am

3 stops57h 57m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

  • Most accurate provider: When it comes to deals on Portland-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-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-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-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 to New Windsor?

Currently, February is the cheapest month in which you can book a flight from Portland to New Windsor (average of $126). Flying from Portland to New Windsor in October is currently the most expensive (average of $257). 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.

  • 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 to New Windsor?

    Currently, February is the cheapest month in which you can book a flight from Portland to New Windsor (average of $126). Flying from Portland to New Windsor in October is currently the most expensive (average of $257). 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.
Portland to John F Kennedy Intl flights
Portland to Newark flights
Portland to LaGuardia flights
Boise to John F Kennedy Intl flights
Boise to Newark flights
Boise to LaGuardia flights
Eugene to John F Kennedy Intl flights
Portland to Buffalo flights
Eugene to Newark flights
Portland to Albany flights
Portland to Rochester flights
Eugene to LaGuardia flights
Portland to Syracuse flights
Medford to John F Kennedy Intl flights
Redmond to John F Kennedy Intl flights
Medford to Newark flights
Medford to LaGuardia flights
Portland to White Plains flights
Redmond to Newark flights
Redmond to LaGuardia flights
Eugene to Albany flights
Boise to Buffalo flights
Boise to Albany flights
Boise to Syracuse flights
Portland to Ithaca flights
Medford to Buffalo flights
Redmond to Buffalo flights
Boise to Rochester flights
Redmond to Albany flights
Portland to Elmira flights
Portland to Watertown flights
Medford to Syracuse flights
Medford to Rochester flights
Eugene to Buffalo flights
Medford to Albany flights
Medford to White Plains flights
Medford to Watertown flights
Eugene to Rochester flights
Portland to Binghamton flights
Medford to Ithaca flights
Redmond to Ithaca flights
Eugene to Syracuse flights
Yakima to Albany flights
Yakima to John F Kennedy Intl flights
Yakima to Newark flights
Medford to Stewart flights
Eugene to Ithaca flights
Eugene to Binghamton flights
Boise to Watertown 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.