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$190+ Cheap flights from New Windsor (SWF) to Oregon

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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PDX
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
1 adult, Economy
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Cheap flight deals from Stewart to Oregon

One-way flights from Stewart to Oregon
Search for one-way flight options from Stewart to Oregon. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/111:52 am
SWF
-
PDX
3 stops36h 31m
Multiple Airlines
Deal found 2/10$190
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 5/2110:28 am
SWF
-
PDX
3 stops26h 20m
Multiple Airlines
Deal found 2/10$257
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 6/276:45 pm
SWF
-
PDX
2 stops22h 03m
Allegiant Air
Deal found 2/12$375
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 6/218:04 pm
SWF
-
PDX
3 stops28h 05m
Multiple Airlines
Deal found 2/11$451
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 6/288:04 pm
SWF
-
PDX
2 stops41h 39m
Allegiant Air
Deal found 2/10$463
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 6/288:04 pm
SWF
-
PDX
3 stops28h 05m
Multiple Airlines
Deal found 2/10$471
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 2/218:24 pm
SWF
-
PDX
3 stops24h 44m
Allegiant Air
Deal found 2/12$714

Find flight deals from Stewart to Oregon

Keep the following information in mind while searching for Stewart to Oregon flight deals. Data was last updated February 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

December

Cheapest in

February

Average price

$338
Provider with most accurate pricing for New York (NYC)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Portland flights.
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Oregon 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 February 13, 2026.
Use the filters below to find and compare flights from New Windsor to Oregon that are best for you.

Fly from

Stewart

Fly to

Oregon

Route

Depart

Return

Price

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Sun 3/1

11:52 am-9:23 pm

3 stops36h 31m

$190

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Thu 5/21

10:28 am-9:48 am

3 stops26h 20m

$257

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Sat 6/27

6:45 pm-1:48 pm

2 stops22h 03m

$375

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Sun 6/21

8:04 pm-9:09 pm

3 stops28h 05m

$451

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Sun 6/28

8:04 pm-10:43 am

2 stops41h 39m

$463

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Sun 6/28

8:04 pm-9:09 pm

3 stops28h 05m

$471

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Sat 2/21

8:24 pm-6:08 pm

3 stops24h 44m

$714

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Best time to book a flight from Stewart to Oregon

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

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

Currently, May is the cheapest month in which you can book a flight from New Windsor to Oregon (average of $147). Flying from New Windsor to Oregon in December is currently the most expensive (average of $258). 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.

Related info for your journey

Find useful and relevant information for your journey from Stewart to Oregon. 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 from for flights from New Windsor to Oregon?

    For a flight from New Windsor to Oregon, you will be flying from Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city.

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

    The most popular route from New Windsor to Oregon is New Windsor Stewart - Portland. You may also consider New Windsor Stewart - Eugene or New Windsor Stewart - Medford.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from New Windsor to Oregon (average of $147). Flying from New Windsor to Oregon in December is currently the most expensive (average of $258). 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.

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