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Stewart

$176+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SWF
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Oregon to Stewart

Keep the following information in mind while searching for Oregon to Stewart flight deals. Data was last updated September 15, 2025.

Popular in

December

Cheapest in

January

Average price

$367
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 ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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Find 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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 12/1111:45 amPDX - SWF
2 stops27h 55mMultiple Airlines
Deal found 9/14$176
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/1512:43 pmPDX - SWF
3 stops42h 58mMultiple Airlines
Deal found 9/13$185
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 11/23:26 pmPDX - SWF
3 stops17h 18mMultiple Airlines
Deal found 9/14$186
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/112:52 pmPDX - SWF
3 stops44h 19mMultiple Airlines
Deal found 9/14$188
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/1512:52 pmPDX - SWF
3 stops43h 19mMultiple Airlines
Deal found 9/14$191
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/2512:43 pmPDX - SWF
2 stops19h 20mMultiple Airlines
Deal found 9/12$195
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/313:26 pmPDX - SWF
3 stops41h 37mMultiple Airlines
Deal found 9/12$232
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/47:15 amPDX - SWF
2 stops32h 06mMultiple Airlines
Deal found 9/14$243
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 9/2612:22 pmBOI - SWF
3 stops44h 41mMultiple Airlines
Deal found 9/13$257
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 10/39:54 pmBOI - SWF
3 stops42h 27mMultiple Airlines
Deal found 9/14$258
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 9/247:15 amPDX - SWF
3 stops48h 48mMultiple Airlines
Deal found 9/13$264
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/245:12 pmMFR - SWF
3 stops44h 43mMultiple Airlines
Deal found 9/13$282

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 September 15, 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 12/11

11:45 am-6:40 pm

2 stops27h 55m

$176

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Wed 10/15

12:43 pm-10:41 am

3 stops42h 58m

$185

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sun 11/2

3:26 pm-11:44 am

3 stops17h 18m

$186

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 11/1

12:52 pm-12:11 pm

3 stops44h 19m

$188

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 10/25

12:43 pm-11:03 am

2 stops19h 20m

$195

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 11/15

12:52 pm-11:03 am

2 stops19h 11m

$212

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Fri 10/31

3:26 pm-12:03 pm

3 stops41h 37m

$232

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 10/4

7:15 am-6:21 pm

2 stops32h 06m

$243

BoiseNew Windsor

BOI - SWF

BOISWF

Boise Air Term. Gowen Fld

Fri 9/26

12:22 pm-11:03 am

3 stops44h 41m

$257

BoiseNew Windsor

BOI - SWF

BOISWF

Boise Air Term. Gowen Fld

Fri 10/3

9:54 pm-6:21 pm

3 stops42h 27m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 19 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, October is the cheapest month in which you can book a flight from Oregon to New Windsor (average of $109). Flying from Oregon to New Windsor in December is currently the most expensive (average of $202). 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 September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to New Windsor as you normally would.

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 Medford - New Windsor Stewart or Portland - New Windsor Stewart, Boise Air Term. Gowen Fld - 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, October is the cheapest month in which you can book a flight from Oregon to New Windsor (average of $109). Flying from Oregon to New Windsor in December is currently the most expensive (average of $202). 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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