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).

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.

Most accurate provider : When it comes to deals on New Windsor-Portland flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on New Windsor-Portland flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from New Windsor-Portland flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on New Windsor-Portland flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Windsor-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

$131+ Cheap Flights from New Windsor to Portland

Q: E

Most trusted provider : When it comes to deals on New Windsor-Portland flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Windsor-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Q: 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.

Q: 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.

Q: 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.

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Find cheap flights from Stewart to Portland with Cheapflights

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Cheap flight deals from Stewart to Portland

One-way

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 October 10, 2026.

Mon 11/167:04 pm -

2 stops19h 03m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 10/8

$131

Wed 11/1812:39 pm -

3 stops25h 28m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 10/6

$163

Sat 10/3112:39 pm -

3 stops26h 33m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 10/9

$181

Sun 11/1512:00 pm -

3 stops50h 07m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 10/7

$191

Mon 11/912:16 pm -

3 stops25h 51m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 10/7

$192

Find flight deals from Stewart to Portland

Most accurate provider	Expedia 1 star
Most trusted provider	Expedia 3 stars
Popular in	December
Cheapest in	February
Average price	$437

Provider with most accurate pricing for New Windsor Stewart-Portland flight deals.

Search Deals

Provider most trusted by Cheapflights users for New Windsor Stewart-Portland flights.

Search Deals

Highest demand for flights based on searches. 9% potential increase in price ($46 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in October 2026

Search Deals

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

New WindsorPortland

SWF New Windsor Stewart - PDX Portland

SWFPDX

New Windsor Stewart

Mon 11/16

7:04 pm-11:07 am

2 stops19h 03m

Portland

Wed 12/31

12:00 am-3:00 am

Nonstop0h 00m

$131

New WindsorPortland

SWF New Windsor Stewart - PDX Portland

SWFPDX

New Windsor Stewart

Sun 11/15

12:00 pm-11:07 am

3 stops50h 07m

Portland

Wed 12/31

12:00 am-3:00 am

Nonstop0h 00m

$181

New WindsorPortland

SWF New Windsor Stewart - PDX Portland

SWFPDX

New Windsor Stewart

Sun 10/25

11:58 am-11:07 am

3 stops50h 09m

Portland

Wed 12/31

12:00 am-3:00 am

Nonstop0h 00m

$217

New WindsorPortland

SWF New Windsor Stewart - PDX Portland

SWFPDX

New Windsor Stewart

Mon 11/2

12:16 pm-11:07 am

3 stops25h 51m

Portland

Wed 12/31

12:00 am-3:00 am

Nonstop0h 00m

$226

New WindsorPortland

SWF New Windsor Stewart - PDX Portland

SWFPDX

New Windsor Stewart

Fri 10/30

5:39 pm-12:12 pm

2 stops45h 33m

Portland

Wed 12/31

12:00 am-3:00 am

Nonstop0h 00m

$256

New WindsorPortland

SWF New Windsor Stewart - PDX Portland

SWFPDX

New Windsor Stewart

Sat 10/24

12:39 pm-10:54 am

3 stops25h 15m

Portland

Wed 12/31

12:00 am-3:00 am

Nonstop0h 00m

$267

New WindsorPortland

SWF New Windsor Stewart - PDX Portland

SWFPDX

New Windsor Stewart

Thu 11/19

6:48 pm-9:32 am

3 stops41h 44m

Portland

Wed 12/31

12:00 am-3:00 am

Nonstop0h 00m

$307

New WindsorPortland

SWF New Windsor Stewart - PDX Portland

SWFPDX

New Windsor Stewart

Mon 10/26

7:01 pm-11:07 am

2 stops19h 06m

Portland

Wed 12/31

12:00 am-3:00 am

Nonstop0h 00m

$323

New WindsorPortland

SWF New Windsor Stewart - PDX Portland

SWFPDX

New Windsor Stewart

Wed 11/4

12:39 pm-11:07 am

2 stops25h 28m

Portland

Wed 12/31

12:00 am-3:00 am

Nonstop0h 00m

$334

New WindsorPortland

SWF New Windsor Stewart - PDX Portland

SWFPDX

New Windsor Stewart

Fri 10/16

8:48 pm-10:54 am

2 stops41h 06m

Portland

Wed 12/31

12:00 am-3:00 am

Nonstop0h 00m

$337

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/8

Sorted by cheapest first

Most accurate provider: When it comes to deals on New Windsor-Portland flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on New Windsor-Portland flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from New Windsor-Portland flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on New Windsor-Portland flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Windsor-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

SWF-PDX

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.

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.

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This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/16. 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

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 October 10, 2026.

Search for one-way flight options from Stewart to Portland. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.

Find flight deals from Stewart to Portland

Most accurate provider

Most trusted provider

Popular in

Cheapest in

Average price

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.

Related info for your journey

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?

Traveling to a place near Portland?

Browse thousands of different options on Cheapflights for your next trip

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

Alternative routes for Stewart to Portland

See prices for flight routes from nearby airports that may be better suited for you.

Complete your trip

Complete your trip to Portland by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Stewart to Portland by cabin class

Find flights from Stewart to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Stewart and Portland flights

Browse other Stewart and Portland flight options. Last updated on October 10, 2026.

Popular flight searches

Check out other popular destinations found by fellow travelers in 2026

Other flights to Portland

Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 10, 2026.

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$131+ Cheap flights from New Windsor to Portland (SWF - PDX)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/16. 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

One-way flights from Stewart to PortlandSearch for one-way flight options from Stewart to Portland. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.

Search for one-way flight options from Stewart to Portland. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.

Find flight deals from Stewart to Portland

Most accurate provider

Most trusted provider

Popular in

Cheapest in

Average price

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.

Related info for your journey

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?

Traveling to a place near Portland?

Browse thousands of different options on Cheapflights for your next trip

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

Alternative routes for Stewart to Portland

See prices for flight routes from nearby airports that may be better suited for you.

Complete your trip

Complete your trip to Portland by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Stewart to Portland by cabin class

Find flights from Stewart to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Stewart and Portland flights

Browse other Stewart and Portland flight options. Last updated on October 10, 2026.

Popular flight searches

Check out other popular destinations found by fellow travelers in 2026

Other flights to Portland

Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 10, 2026.

100% Free

Book with Flexibility

Travel Smart

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 October 10, 2026.