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Stewart

$193+ 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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SWF
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$527
(Mytrip)

One-way from

$193
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$398
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. 6% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Mytrip deal was found by Cheapflights users on 7/30. 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 8/147:52 pmPDX - SWF
3 stops19h 55mMultiple Airlines
Mon 8/187:37 pmSWF - PDX
3 stops25h 09mMultiple Airlines
Deal found 7/30$527

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 July 31, 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 8/14

7:52 pm-6:47 pm

3 stops19h 55m

New Windsor Stewart

Mon 8/18

7:37 pm-5:46 pm

3 stops25h 09m

$527

BoiseNew Windsor

BOI - SWF

BOISWF

Boise Air Term. Gowen Fld

Thu 8/21

6:06 pm-4:46 pm

2 stops20h 40m

$193

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Sat 11/15

11:44 am-5:24 pm

2 stops26h 40m

$203

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Fri 8/8

4:37 pm-5:01 pm

2 stops21h 24m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 August is currently the most expensive (average of $206). 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 July 31, 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.

Reviews of airlines servicing Stewart

Get insights into the airlines that provide service to Stewart. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Stewart. Reviews last updated July 31, 2025.
Get a feel of what it's like to fly with Allegiant Air from Oregon to New Windsor by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Allegiant Air
7.2
Good
702 reviews

Overall

7.2

Boarding

7.6

Food

5.9

Entertainment

5.5

Comfort

6.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.
Allegiant Air
7.2
Good
702 reviews
Allegiant Air
7.2
Good
702 reviews

Overall

7.2

Boarding

7.6

Food

5.9

Entertainment

5.5

Comfort

6.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.

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 Boise Air Term. Gowen Fld - New Windsor Stewart or Medford - New Windsor Stewart, Portland - 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 August is currently the most expensive (average of $206). 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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