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Stewart

$179+ Cheap flights from Oregon to New Windsor (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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SWF
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap flight deals from Oregon to Stewart

One-way flights from Oregon to Stewart
Search for one-way flight options from Oregon to Stewart. Find affordable one-way fares based on user searches. Data last updated December 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/15. 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 1/812:05 pmPDX - SWF
2 stops27h 38mMultiple Airlines
Deal found 12/15$179
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 1/269:22 pmPDX - SWF
3 stops59h 11mMultiple Airlines
Deal found 12/15$181
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 1/2911:28 amPDX - SWF
3 stops28h 15mMultiple Airlines
Deal found 12/15$197
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 1/3010:44 amPDX - SWF
3 stops44h 14mMultiple Airlines
Deal found 12/16$199
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 2/811:09 amPDX - SWF
3 stops28h 34mMultiple Airlines
Deal found 12/16$211
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 1/105:26 pmPDX - SWF
2 stops15h 07mMultiple Airlines
Deal found 12/15$255
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 1/1112:10 pmPDX - SWF
2 stops27h 33mMultiple Airlines
Deal found 12/16$260
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 4/2510:30 amPDX - SWF
3 stops45h 20mMultiple Airlines
Deal found 12/16$360
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 1/135:55 pmBOI - SWF
3 stops39h 38mMultiple Airlines
Deal found 12/15$378
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 1/175:55 pmBOI - SWF
3 stops46h 48mMultiple Airlines
Deal found 12/14$420
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 1/69:03 pmMFR - SWF
3 stops58h 16mMultiple Airlines
Deal found 12/15$423
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 2/165:41 pmBOI - SWF
3 stops45h 15mAllegiant Air
Deal found 12/15$435

Find flight deals from Oregon to Stewart

Keep the following information in mind while searching for Oregon to Stewart flight deals. Data was last updated December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Popular in

December

Cheapest in

February

Average price

$529
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 ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon 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 December 16, 2025.
Use the filters below to find and compare flights from Oregon to New Windsor that are best for you.

Fly from

Oregon

Fly to

Stewart

Route

Depart

Return

Price

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Thu 1/8

12:05 pm-6:43 pm

2 stops27h 38m

$179

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Mon 1/26

9:22 pm-11:33 am

3 stops59h 11m

$181

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Fri 1/30

10:44 am-9:58 am

3 stops44h 14m

$199

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Thu 1/29

11:28 am-10:19 am

2 stops19h 51m

$208

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sun 2/8

11:09 am-6:43 pm

3 stops28h 34m

$211

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 1/10

5:26 pm-11:33 am

2 stops15h 07m

$255

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sun 1/11

1:02 pm-6:43 pm

3 stops26h 41m

$255

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 4/25

10:30 am-10:50 am

3 stops45h 20m

$360

BoiseNew Windsor

BOI - SWF

BOISWF

Boise Air Term. Gowen Fld

Tue 1/13

5:55 pm-11:33 am

3 stops39h 38m

$378

BoiseNew Windsor

BOI - SWF

BOISWF

Boise Air Term. Gowen Fld

Sat 1/17

5:55 pm-6:43 pm

3 stops46h 48m

$420

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 22 results
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Best time to book a flight from Oregon to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Oregon 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 Oregon to New Windsor

What is the cheapest month to book a flight from Oregon to New Windsor?

Currently, February is the cheapest month in which you can book a flight from Oregon to New Windsor (average of $120). Flying from Oregon 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.

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

Find hourly flight availability from Oregon 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 December 16, 2025.

One of the essential ways to save on airfare from Oregon to New Windsor is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 36% on airfare.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to New Windsor from Oregon?

    If you book a flight to New Windsor from Oregon, you will be flying to Stewart, which is the city’s only airport. New Windsor Stewart (SWF) is located 4.3 mi from the center of New Windsor.

  • What are the most popular routes from Oregon to New Windsor?

    While some choose either Portland - New Windsor Stewart or Boise Air Term. Gowen Fld - New Windsor Stewart, Medford - New Windsor Stewart is the most popular route from Oregon to New Windsor.

  • Can I find deals for flights from Oregon to Stewart that include hotel bookings?

    Yes. In addition to deals on Oregon to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oregon to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Stewart.

  • Can I find deals for business class flights from Oregon to Stewart?

    Yes. Cheapflights offers flight deals from Oregon 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 Oregon to New Windsor?

    Currently, February is the cheapest month in which you can book a flight from Oregon to New Windsor (average of $120). Flying from Oregon 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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