In terms of precipitation, rainfall in Portland ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Portland when rainfall is around 0.7 in.

If weather is an important factor for your trip to Portland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

How far in advance should I book a flight from New Windsor to Portland?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 56 days in advance, which can save you up to 52% on flights from New Windsor to Portland compared to booking the week you need them. Waiting 56 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $487. For sooner than that we have options available in the next 3 days from $587.

What is the cheapest month to fly from New Windsor to Portland?

Flights from New Windsor to Portland lean towards being more expensive in December. Prices are generally better when you fly from New Windsor to Portland in January, with the cheapest ticket starting at $148.

What is the cheapest time of day to fly from SWF to PDX?

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

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

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

How can I find direct flights from Stewart to Portland?

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

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

Yes. Cheapflights offers flight deals from Stewart to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$195+ Flights from New Windsor to Portland

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1. Tell us where you want to go

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Cheap flight deals from Stewart to Portland

Round-trip from	$634 (Mytrip)
One-way from	$201 (Mytrip)
Popular in	December
Cheapest in	January
Average price	$487

From New Windsor Stewart to Portland

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One-way flight from New Windsor Stewart to Portland

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Highest demand for flights based on searches. 4% potential increase in price ($19 potential increase over avg. RT price).

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Cheapest flight prices on average. 3% potential price decrease ($16 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 Stewart to Portland

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

Mon 7/147:56 pmSWF - PDX

3 stops40h 22mMultiple Airlines

Thu 7/173:10 pmPDX - SWF

2 stops24h 56mMultiple Airlines

Deal found 6/30

$436

Best flights from Stewart to Portland
Discover carefully curated flight deals from Stewart to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 30, 2025.

Tue 7/1512:36 pmSWF - PDX

2 stops23h 42mMultiple Airlines

Sat 7/193:10 pmPDX - SWF

3 stops23h 42mMultiple Airlines

Deal found 6/30

$634

Last-minute flights from Stewart to Portland
Discover last-minute flight deals from Stewart to Portland. Data last updated June 30, 2025 and is based on user searches.

Mon 7/77:56 pmSWF - PDX

3 stops24h 48mMultiple Airlines

Thu 7/106:02 pmPDX - SWF

2 stops22h 04mMultiple Airlines

Deal found 6/30

$671

Mon 7/147:56 pmSWF - PDX

3 stops40h 22mMultiple Airlines

Thu 7/173:10 pmPDX - SWF

2 stops24h 56mMultiple Airlines

Deal found 6/30

$436

One-way flights from Stewart to Portland
Search for one-way flight options from Stewart to Portland. Find affordable one-way fares based on user searches. Data last updated June 30, 2025.

Mon 7/217:56 pmSWF - PDX

3 stops40h 22mMultiple Airlines

Deal found 6/30

$201

Sun 8/178:33 pmSWF - PDX

2 stops21h 58mAllegiant Air

Deal found 6/29

$204

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Mon 7/14

7:56 pm-9:18 am

3 stops40h 22m

Portland

Thu 7/17

3:10 pm-7:06 pm

2 stops24h 56m

$436

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Fri 8/1

7:56 pm-9:18 am

3 stops40h 22m

$195

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Sun 8/17

8:33 pm-3:31 pm

2 stops21h 58m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Best time to book a flight from Stewart to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland 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 Portland

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

Currently, November is the cheapest month in which you can book a flight from New Windsor to Portland (average of $277). Flying from New Windsor to Portland in March is currently the most expensive (average of $369). 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.

Reviews of airlines servicing Portland

Peruse reviews from past customers who have flown with Allegiant Air from New Windsor to Portland to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Allegiant Air

7.2

Good

710 reviews

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

710 reviews

Allegiant Air

7.2

Good

710 reviews

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

Can I find deals for flights from Stewart to Portland that include hotel bookings?
Yes. In addition to deals on Stewart to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Stewart to Portland?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Portland.
Can I find deals for business class flights from Stewart to Portland?
Yes. Cheapflights offers flight deals from Stewart to Portland 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 Portland?
Currently, November is the cheapest month in which you can book a flight from New Windsor to Portland (average of $277). Flying from New Windsor to Portland in March is currently the most expensive (average of $369). 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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$195+ Cheap flights from New Windsor to Portland (SWF - PDX)

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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Stewart to Portland with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Stewart to Portland

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Stewart to Portland

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

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

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to Portland that are best for you.

Best time to book a flight from Stewart to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Stewart with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from New Windsor to Portland

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

Reviews of airlines servicing Portland

Peruse reviews from past customers who have flown with Allegiant Air from New Windsor to Portland to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Stewart to Portland. 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 Stewart to Portland that include hotel bookings?

How can I find direct flights from Stewart to Portland?

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

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

Traveling to a place near New Windsor?

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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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