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$185+ 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 12/19. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PDX
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find 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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/198:11 pmSWF - PDX
2 stops42h 32mMultiple Airlines
Deal found 10/28$185
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/209:45 amSWF - PDX
2 stops28h 58mMultiple Airlines
Deal found 10/28$191
This Mytrip deal was found by Cheapflights users on 10/29. 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.
Mon 12/812:27 pmSWF - MFR
2 stops25h 07mMultiple Airlines
Deal found 10/29$192
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/209:45 amSWF - EUG
2 stops31h 31mMultiple Airlines
Deal found 10/28$257
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:23 pmSWF - PDX
3 stops25h 55mMultiple Airlines
Deal found 10/27$375
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/1811:09 amSWF - EUG
3 stops50h 08mAllegiant Air
Deal found 10/28$417
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/66:14 pmSWF - PDX
3 stops44h 42mMultiple Airlines
Deal found 10/28$526

Cheap flight deals from Stewart to Oregon

Keep the following information in mind while searching for Stewart to Oregon flight deals. Data was last updated October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Popular in

December

Cheapest in

January

Average price

$377
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. 6% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 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 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 October 30, 2025.
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

Fri 12/19

8:11 pm-11:43 am

2 stops42h 32m

$185

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Sat 12/20

9:45 am-11:43 am

2 stops28h 58m

$191

New WindsorMedford

SWF - MFR

SWFMFR

New Windsor Stewart

Mon 12/8

12:27 pm-10:34 am

2 stops25h 07m

$192

New WindsorEugene

SWF - EUG

SWFEUG

New Windsor Stewart

Sat 12/20

9:45 am-2:16 pm

2 stops31h 31m

$257

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Mon 12/22

8:25 pm-5:14 pm

3 stops23h 49m

$353

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Thu 11/20

6:23 pm-5:18 pm

3 stops25h 55m

$375

New WindsorEugene

SWF - EUG

SWFEUG

New Windsor Stewart

Thu 12/18

11:09 am-10:17 am

3 stops50h 08m

$417

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Thu 11/6

6:14 pm-11:56 am

3 stops44h 42m

$526

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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, March is the cheapest month in which you can book a flight from New Windsor to Oregon (average of $128). Flying from New Windsor to Oregon in November is currently the most expensive (average of $264). 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, March is the cheapest month in which you can book a flight from New Windsor to Oregon (average of $128). Flying from New Windsor to Oregon in November is currently the most expensive (average of $264). 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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