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Stewart

$181+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SWF
Aug 24 — Aug 311
Mon 8/24
Mon 8/31
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 July 25, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/22. 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 9/233:22 pm
PDX
-
SWF
3 stops39h 54m
Multiple Airlines
Deal found 7/22$181
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Tue 9/15:56 pm
PDX
-
SWF
3 stops45h 44m
Multiple Airlines
Deal found 7/20$182
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
Wed 9/25:56 pm
PDX
-
SWF
3 stops21h 44m
Multiple Airlines
Deal found 7/21$188
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 10/73:22 pm
PDX
-
SWF
2 stops38h 33m
Multiple Airlines
Deal found 7/22$190
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
Thu 9/2412:38 pm
PDX
-
SWF
2 stops18h 38m
Multiple Airlines
Deal found 7/24$196
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Mon 9/143:22 pm
PDX
-
SWF
2 stops41h 17m
Multiple Airlines
Deal found 7/22$201
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
Sat 9/512:20 pm
PDX
-
SWF
3 stops27h 20m
Multiple Airlines
Deal found 7/21$202
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 9/223:22 pm
PDX
-
SWF
3 stops40h 01m
Multiple Airlines
Deal found 7/22$209

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 July 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

December

Cheapest in

February

Average price

$429
Provider with most accurate pricing for Portland-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-New York (NYC) flights.
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 25, 2026.
Use the filters below to find and compare flights from Portland to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest one-way

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Tue 9/1

5:56 pm-6:40 pm

3 stops45h 44m

$205

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Wed 9/2

5:56 pm-6:40 pm

3 stops21h 44m

$214
Quickest one-way

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 9/19

5:30 pm-10:16 am

2 stops13h 46m

$219

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 9/26

3:22 pm-10:16 am

2 stops15h 54m

$230

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Tue 8/18

5:56 pm-12:10 pm

3 stops39h 14m

$243

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 8/29

5:56 pm-11:06 am

2 stops38h 10m

$263

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Mon 10/5

12:38 pm-11:39 am

3 stops44h 01m

$269

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Thu 8/20

1:47 pm-4:49 pm

2 stops24h 02m

$275

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sun 8/23

1:47 pm-11:08 am

3 stops42h 21m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Sorted by cheapest first

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.

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.

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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