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Stewart

$170+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SWF
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Find 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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Thu 12/412:51 pmPDX - SWF
3 stops19h 53mMultiple Airlines
Deal found 10/26$170
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Thu 1/812:47 pmPDX - SWF
3 stops19h 44mMultiple Airlines
Deal found 10/26$188
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Mon 11/243:59 pmPDX - SWF
3 stops40h 28mMultiple Airlines
Deal found 10/26$194
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Tue 12/305:39 pmPDX - SWF
2 stops20h 05mMultiple Airlines
Deal found 10/26$202
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Sat 11/1512:52 pmPDX - SWF
3 stops43h 19mMultiple Airlines
Deal found 10/26$224
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Sat 11/812:52 pmPDX - SWF
3 stops43h 19mMultiple Airlines
Deal found 10/26$226
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 1/312:37 pmPDX - SWF
3 stops44h 07mMultiple Airlines
Deal found 10/27$230
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Sat 11/222:30 pmPDX - SWF
3 stops40h 37mMultiple Airlines
Deal found 10/26$235
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Sat 12/139:48 amPDX - SWF
3 stops46h 49mMultiple Airlines
Deal found 10/26$236
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Sun 11/163:26 pmPDX - SWF
3 stops40h 00mMultiple Airlines
Deal found 10/26$241
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/252:31 pmPDX - SWF
3 stops41h 32mMultiple Airlines
Deal found 10/27$246

Cheap 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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Popular in

December

Cheapest in

January

Average price

$377
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. 7% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 28, 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

PDX - SWF

PDXSWF

Portland

Thu 12/4

12:51 pm-11:44 am

3 stops19h 53m

$170

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Thu 1/8

12:47 pm-11:31 am

3 stops19h 44m

$188

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Mon 11/24

3:59 pm-11:27 am

3 stops40h 28m

$194

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 12/6

9:48 am-11:37 am

2 stops46h 49m

$194

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Tue 12/30

5:39 pm-4:44 pm

2 stops20h 05m

$202

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 11/15

12:52 pm-11:11 am

3 stops43h 19m

$224

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 11/8

12:52 pm-11:11 am

3 stops43h 19m

$226

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 1/3

12:37 pm-11:44 am

3 stops44h 07m

$230

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 11/22

2:30 pm-10:07 am

3 stops40h 37m

$235

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 12/13

9:48 am-11:37 am

3 stops46h 49m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Compare providers for flights from Portland to Stewart

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 Portland to Stewart in October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Portland-New Windsor flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland-New Windsor flight deals on Cheapflights vs. eDreams >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 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 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 $104). Flying from Portland to New Windsor in October is currently the most expensive (average of $254). 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.

What is the cheapest time of day to fly from PDX to SWF?

Find hourly flight availability from Portland to Stewart. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 28, 2025.

When flying from Portland to New Windsor, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 64% versus a flight at noon.

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 $104). Flying from Portland to New Windsor in October is currently the most expensive (average of $254). 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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