HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$334+ 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 12/22. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PDX
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Portland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 December 8, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/6. 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.
Mon 12/227:10 pmSWF - PDX
3 stops46h 50mMultiple Airlines
Deal found 12/6$334
This Kiwi.com deal was found by Cheapflights users on 12/8. 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 5/225:53 pmSWF - PDX
2 stops47h 01mAllegiant Air
Deal found 12/8$355
This Kiwi.com deal was found by Cheapflights users on 12/8. 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.
Tue 12/2311:43 amSWF - PDX
3 stops50h 54mMultiple Airlines
Deal found 12/8$386
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 stops24h 57mMultiple Airlines
Deal found 12/6$398
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 12/1811:43 amSWF - PDX
2 stops38h 10mMultiple Airlines
Deal found 12/6$412
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 12/207:50 pmSWF - PDX
3 stops51h 00mMultiple Airlines
Deal found 12/6$416

Find flight deals from Stewart to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Portland (PDX). 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 December 8, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Popular in

December

Cheapest in

January

Average price

$567
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. 8% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Portland 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 December 8, 2025.
Use the filters below to find and compare flights from New Windsor to Portland that are best for you.

Fly from

Stewart

Fly to

Portland

Route

Depart

Return

Price

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Mon 12/22

7:10 pm-3:00 pm

3 stops46h 50m

$334

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Fri 5/22

5:53 pm-1:54 pm

2 stops47h 01m

$355

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Fri 12/19

8:11 pm-6:08 pm

2 stops24h 57m

$398

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Tue 12/23

6:28 pm-1:24 pm

3 stops45h 56m

$412

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Thu 12/18

11:43 am-10:53 pm

2 stops38h 10m

$412

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Sat 12/20

7:50 pm-7:50 pm

3 stops51h 00m

$416

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Compare providers for flights from Stewart to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart to Portland in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New Windsor-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Portland flight deals on Cheapflights vs. FlightHub >95% 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.
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, March is the cheapest month in which you can book a flight from New Windsor to Portland (average of $128). Flying from New Windsor to Portland in November is currently the most expensive (average of $261). 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 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?

    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, March is the cheapest month in which you can book a flight from New Windsor to Portland (average of $128). Flying from New Windsor to Portland in November is currently the most expensive (average of $261). 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
Vancouver
Seaside
Clackamas
Lincoln City
Lake Oswego
Beaverton
McMinnville
Hillsboro
Troutdale
Cannon Beach
Long Beach
Longview
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Gresham

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.
John F Kennedy Intl to Portland flights
Newark to Portland flights
LaGuardia to Portland flights
John F Kennedy Intl to Boise flights
Newark to Boise flights
John F Kennedy Intl to Eugene flights
Newark to Eugene flights
LaGuardia to Boise flights
Syracuse to Portland flights
LaGuardia to Eugene flights
John F Kennedy Intl to Redmond flights
Newark to Redmond flights
LaGuardia to Redmond flights
Albany to Portland flights
Albany to Boise flights
Rochester to Portland flights
Syracuse to Eugene flights
John F Kennedy Intl to Medford flights
Syracuse to Boise flights
Buffalo to Portland flights
Newark to Medford flights
Albany to Eugene flights
White Plains to Portland flights
LaGuardia to Medford flights
Newark to North Bend flights
Buffalo to Eugene flights
Ithaca to Redmond flights
Buffalo to Medford flights
Buffalo to Boise flights
Rochester to Boise flights
Syracuse to Medford flights
White Plains to Eugene flights
Ithaca to Portland flights
Rochester to Eugene flights
Syracuse to Redmond flights
Buffalo to Redmond flights
Albany to Redmond flights
Elmira to Portland flights
Albany to Medford flights
Rochester to Medford flights
John F Kennedy Intl to Yakima flights
White Plains to Boise flights
Elmira to Redmond flights
Binghamton to Medford flights
Rochester to Redmond flights
Niagara Falls to Portland flights
Newark to Yakima flights
LaGuardia to Yakima flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.