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Stewart

$176+ Cheap flights from Portland to New Windsor (PDX - 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 7/17. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SWF
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Portland to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2025.

Round-trip from

$385
(Mytrip)

One-way from

$176
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$427
From Portland to New Windsor Stewart
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One-way flight from Portland to New Windsor Stewart
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Highest demand for flights based on searches. 7% potential increase in price ($30 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 June 2025
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Find flight deals from Portland to Stewart

Cheapest flights from Portland to Stewart
Explore the most affordable flight options available from Portland to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/259:22 amPDX - SWF
2 stops28h 36mMultiple Airlines
Mon 7/287:56 pmSWF - PDX
3 stops40h 22mMultiple Airlines
Deal found 6/11$385
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/246:02 pmPDX - SWF
2 stops22h 04mAllegiant Air
Sun 7/2711:13 amSWF - PDX
2 stops23h 19mAllegiant Air
Deal found 6/10$422

Cheapflights Fare Finder

Customize your flight search to find flights from Portland 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 June 12, 2025.
Use the filters below to find and compare flights from Portland to New Windsor that are best for you.

Fly from

Portland

Fly to

Stewart

Route

Depart

Return

Price

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Fri 7/25

9:22 am-4:58 pm

2 stops28h 36m

New Windsor Stewart

Mon 7/28

7:56 pm-9:18 am

3 stops40h 22m

$385

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Thu 7/24

6:02 pm-7:06 pm

2 stops22h 04m

New Windsor Stewart

Sun 7/27

11:13 am-7:32 am

2 stops23h 19m

$422

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Thu 7/17

3:10 pm-7:06 pm

2 stops24h 56m

$176

PortlandNew Windsor

PDX - SWF

PDXSWF

Portland

Fri 7/18

9:22 am-4:58 pm

2 stops28h 36m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Best time to book a flight from Portland to Stewart

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

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

Currently, October is the cheapest month in which you can book a flight from Portland to New Windsor (average of $109). Flying from Portland to New Windsor in August is currently the most expensive (average of $219). 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 PDX to SWF?

Find hourly flight availability from Portland 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 June 12, 2025.

When flying from Portland to New Windsor, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 June 12, 2025.
Allegiant Air
7.3
Good
725 reviews

Boarding

7.6

Comfort

6.8

Entertainment

5.5

Overall

7.3

Food

5.9

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
7.3
Good
725 reviews
Allegiant Air
7.3
Good
725 reviews

Boarding

7.6

Comfort

6.8

Entertainment

5.5

Overall

7.3

Food

5.9

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 Portland to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland 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 Portland to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Portland to New Windsor (average of $109). Flying from Portland to New Windsor in August is currently the most expensive (average of $219). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Kingston

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