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Stewart

$198+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SWF
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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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 January 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Fri 2/2710:18 pm
PDX
-
SWF
3 stops56h 55m
Multiple Airlines
Deal found 1/24$198
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Thu 5/712:52 pm
PDX
-
SWF
3 stops43h 33m
Multiple Airlines
Deal found 1/25$227
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Fri 4/1712:52 pm
PDX
-
SWF
3 stops43h 03m
Multiple Airlines
Deal found 1/25$236
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Wed 4/221:48 pm
PDX
-
SWF
3 stops18h 07m
Multiple Airlines
Deal found 1/26$256
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 4/1812:27 pm
PDX
-
SWF
3 stops19h 28m
Multiple Airlines
Deal found 1/25$260
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Sun 3/297:56 pm
PDX
-
SWF
3 stops36h 56m
Multiple Airlines
Deal found 1/24$262
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Tue 3/319:43 am
PDX
-
SWF
3 stops44h 56m
Multiple Airlines
Deal found 1/25$264
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 3/2810:24 am
PDX
-
SWF
2 stops21h 44m
Multiple Airlines
Deal found 1/24$274
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Wed 4/291:48 pm
PDX
-
SWF
3 stops18h 07m
Multiple Airlines
Deal found 1/25$277
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Fri 4/311:58 am
PDX
-
SWF
3 stops42h 41m
Multiple Airlines
Deal found 1/24$296
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Tue 5/121:48 pm
PDX
-
SWF
3 stops40h 10m
Multiple Airlines
Deal found 1/24$300

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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Popular in

December

Cheapest in

February

Average price

$359
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. 10% potential increase in price ($43 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 January 26, 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

Fri 2/27

10:18 pm-10:13 am

3 stops56h 55m

$198

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Thu 5/7

12:52 pm-11:25 am

3 stops43h 33m

$227

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Fri 4/17

12:52 pm-10:55 am

3 stops43h 03m

$236

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Wed 4/22

1:48 pm-10:55 am

3 stops18h 07m

$256

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 4/18

12:27 pm-10:55 am

3 stops19h 28m

$260

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sun 3/29

7:56 pm-11:52 am

3 stops36h 56m

$262

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Tue 3/31

9:43 am-9:39 am

3 stops44h 56m

$264

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Fri 4/3

11:58 am-9:39 am

3 stops42h 41m

$296

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Tue 5/12

1:48 pm-8:58 am

3 stops40h 10m

$300

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Tue 5/5

1:48 pm-8:58 am

3 stops40h 10m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

  • 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 $127). 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 $127). 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

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