$171+ Cheap flights from Portland to New Windsor (PDX - SWF)
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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Portland to Stewart 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 Portland to Stewart
One-way flights from Portland to StewartSearch for one-way flight options from Portland to Stewart. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
Search for one-way flight options from Portland to Stewart. 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 9/7. 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.
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.
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.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
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.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
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.
Find 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 September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Popular in | December |
Cheapest in | February |
Average price | $394 |
Cheapflights Fare Finder
Use the filters below to find and compare flights from Portland to New Windsor that are best for you.
Fly from
Fly to
Route
Depart
Return
PortlandNew Windsor
PDX Portland - SWF New Windsor Stewart
PDXSWF
Portland
Sun 11/1
12:07 pm-6:11 pm
2 stops27h 04m
New Windsor Stewart
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
PortlandNew Windsor
PDX Portland - SWF New Windsor Stewart
PDXSWF
Portland
Tue 10/13
11:49 am-11:39 am
3 stops20h 50m
New Windsor Stewart
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
PortlandNew Windsor
PDX Portland - SWF New Windsor Stewart
PDXSWF
Portland
Fri 9/18
12:38 pm-11:39 am
3 stops20h 01m
New Windsor Stewart
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
PortlandNew Windsor
PDX Portland - SWF New Windsor Stewart
PDXSWF
Portland
Thu 10/1
12:38 pm-11:39 am
3 stops44h 01m
New Windsor Stewart
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
PortlandNew Windsor
PDX Portland - SWF New Windsor Stewart
PDXSWF
Portland
Sun 10/4
12:38 pm-6:23 pm
2 stops26h 45m
New Windsor Stewart
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
PortlandNew Windsor
PDX Portland - SWF New Windsor Stewart
PDXSWF
Portland
Thu 9/24
12:38 pm-10:08 am
3 stops18h 30m
New Windsor Stewart
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
PortlandNew Windsor
PDX Portland - SWF New Windsor Stewart
PDXSWF
Portland
Thu 10/15
11:06 am-11:39 am
3 stops45h 33m
New Windsor Stewart
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
PortlandNew Windsor
PDX Portland - SWF New Windsor Stewart
PDXSWF
Portland
Sat 9/19
12:24 pm-10:16 am
2 stops18h 52m
New Windsor Stewart
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
PortlandNew Windsor
PDX Portland - SWF New Windsor Stewart
PDXSWF
Portland
Sun 9/13
12:24 pm-11:36 am
3 stops20h 12m
New Windsor Stewart
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
PortlandNew Windsor
PDX Portland - SWF New Windsor Stewart
PDXSWF
Portland
Mon 11/2
12:31 pm-11:39 am
3 stops44h 08m
New Windsor Stewart
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
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.
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.