$204+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PDX
Oct 10 — Oct 171
Round-trip
1 adult, Economy
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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
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 September 10, 2026.
Search for one-way flight options from Stewart to Portland. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Wed 11/1812:39 pm -
3 stops25h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Sun 12/611:06 am -
2 stops32h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Sat 11/712:39 pm -
3 stops25h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/27:01 pm -
2 stops19h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 12/512:39 pm -
3 stops55h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 9/1212:39 pm -
3 stops26h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/1912:39 pm -
3 stops26h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$249
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 September 10, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Popular in | December |
Cheapest in | February |
Average price | $436 |
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 7,457,451 searches. Data last updated September 10, 2026.
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
Cheapest round-trip
New WindsorPortland
SWF New Windsor Stewart - PDX Portland
SWFPDX
New Windsor Stewart
Sat 11/7
12:39 pm-11:12 am
3 stops25h 33m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$214
Quickest round-trip
New WindsorPortland
SWF New Windsor Stewart - PDX Portland
SWFPDX
New Windsor Stewart
Mon 11/2
7:01 pm-11:07 am
2 stops19h 06m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$232
New WindsorPortland
SWF New Windsor Stewart - PDX Portland
SWFPDX
New Windsor Stewart
Sat 12/5
12:39 pm-3:40 pm
2 stops30h 01m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$255
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
$255
New WindsorPortland
SWF New Windsor Stewart - PDX Portland
SWFPDX
New Windsor Stewart
Wed 11/18
12:39 pm-11:07 am
2 stops25h 28m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$255
New WindsorPortland
SWF New Windsor Stewart - PDX Portland
SWFPDX
New Windsor Stewart
Wed 11/11
12:39 pm-11:36 am
3 stops25h 57m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$276
New WindsorPortland
SWF New Windsor Stewart - PDX Portland
SWFPDX
New Windsor Stewart
Thu 11/12
11:00 am-11:36 am
3 stops27h 36m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$278
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
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.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsBeaverton
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