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Stewart

$147+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SWF
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$446
(Mytrip)

One-way from

$147
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$377
Provider with most accurate pricing for Portland-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Portland-New York (NYC) flights.
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From Oregon to New Windsor Stewart
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One-way flight from Oregon to New Windsor Stewart
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Highest demand for flights based on searches. 7% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Oregon to Stewart

Cheapest flights from Oregon to Stewart
Explore the most affordable flight options available from Oregon to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:07 pmMFR - SWF
3 stops16h 30mMultiple Airlines
Mon 12/812:27 pmSWF - MFR
2 stops25h 07mMultiple Airlines
Deal found 10/30$446

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 October 30, 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

MedfordNew Windsor

MFR - SWF

MFRSWF

Medford

Thu 12/4

4:07 pm-11:37 am

3 stops16h 30m

New Windsor Stewart

Mon 12/8

12:27 pm-10:34 am

2 stops25h 07m

$446

BoiseNew Windsor

BOI - SWF

BOISWF

Boise Air Term. Gowen Fld

Thu 1/15

12:54 pm-11:31 am

3 stops20h 37m

$147

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 12/13

9:48 am-11:37 am

3 stops46h 49m

$186

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Thu 12/18

2:29 pm-6:06 pm

2 stops24h 37m

$191

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Thu 12/11

12:51 pm-11:44 am

3 stops19h 53m

$203

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Fri 12/5

12:55 pm-11:03 am

3 stops43h 08m

$219

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

Fri 12/12

12:55 pm-11:03 am

3 stops43h 08m

$231

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 11/22

2:30 pm-10:07 am

3 stops40h 37m

$240

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sun 11/16

3:26 pm-10:26 am

3 stops40h 00m

$242

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 18 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 $104). Flying from Oregon 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 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 October 30, 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 at noon tend to be the most expensive. A flight in the evening could potentially save you up to 51% 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 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, February is the cheapest month in which you can book a flight from Oregon to New Windsor (average of $104). Flying from Oregon 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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