$162+ Cheap flights from Portland, ME to New Windsor (PWM - 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SWF
Nov 25 — Dec 21
Round-trip
1 adult, Economy
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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
Cheapest
Best
Last-minute
One-way
Cheapest flights from Portland to StewartExplore the most affordable flight options available from Portland to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 26, 2026.
Explore the most affordable flight options available from Portland to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/105:09 pm -
1 stop18h 30m
Thu 11/1210:56 am -
1 stop22h 12m
Deal found 10/25![Breeze Airways logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/27:12 pm -
1 stop14h 36m
Fri 12/411:03 am -
1 stop22h 05m
Deal found 10/22![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/35:09 pm -
1 stop18h 30m
Sat 11/712:39 pm -
2 stops20h 42m
Deal found 10/21![Breeze Airways logo]()
$424
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/35:09 pm -
1 stop18h 30m
Mon 11/95:49 pm -
2 stops39h 19m
Deal found 10/21![Multiple Airlines logo]()
$445
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/35:09 pm -
1 stop18h 30m
Sun 11/810:56 am -
1 stop22h 12m
Deal found 10/21![Breeze Airways logo]()
$447
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/115:09 pm -
2 stops17h 07m
Fri 11/135:30 pm -
1 stop15h 38m
Deal found 10/23![Multiple Airlines logo]()
$489
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/99:48 am -
1 stop24h 38m
Sun 12/1311:06 am -
1 stop22h 02m
Deal found 10/22![Breeze Airways logo]()
$520
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/912:28 pm -
2 stops21h 58m
Sun 12/1311:06 am -
1 stop22h 02m
Deal found 10/22![Multiple Airlines logo]()
$536
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/76:31 pm -
2 stops16h 39m
Thu 11/1210:56 am -
1 stop22h 12m
Deal found 10/23![Multiple Airlines logo]()
$543
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/35:09 pm -
1 stop18h 30m
Thu 11/510:56 am -
1 stop22h 12m
Deal found 10/21![Breeze Airways logo]()
$545
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 10/289:48 am -
1 stop24h 28m
Sat 10/3112:39 pm -
2 stops21h 42m
Deal found 10/21![Breeze Airways logo]()
$571
Best flights from Portland to StewartDiscover carefully curated flight deals from Portland to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 26, 2026.
Discover carefully curated flight deals from Portland to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/27:12 pm -
1 stop14h 36m
Fri 12/411:03 am -
1 stop22h 05m
Deal found 10/22![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/53:10 pm -
2 stops20h 26m
Sun 11/810:56 am -
1 stop22h 12m
Deal found 10/25![Breeze Airways logo]()
$740
This FlightHub deal was found by Cheapflights users on 10/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:35 pm -
3 stops18h 04m
Sun 12/611:06 am -
1 stop22h 02m
Deal found 10/24![Breeze Airways logo]()
$750
This Booking.com deal was found by Cheapflights users on 10/25. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/133:53 pm -
2 stops19h 46m
Sun 11/1510:56 am -
1 stop22h 12m
Deal found 10/25![Breeze Airways logo]()
$794
This FlightHub deal was found by Cheapflights users on 10/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/203:53 pm -
2 stops19h 46m
Sun 11/2210:56 am -
1 stop22h 12m
Deal found 10/25![Breeze Airways logo]()
$845
This Justfly.com deal was found by Cheapflights users on 10/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:53 pm -
2 stops19h 46m
Sun 11/810:56 am -
1 stop22h 12m
Deal found 10/22![Breeze Airways logo]()
$875
This KAYAK deal was found by Cheapflights users on 10/25. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:31 am -
2 stops24h 08m
Thu 11/1210:56 am -
1 stop22h 12m
Deal found 10/25![Breeze Airways logo]()
$883
This KAYAK deal was found by Cheapflights users on 10/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/211:03 am -
2 stops24h 36m
Thu 3/410:56 am -
1 stop22h 12m
Deal found 10/21![Breeze Airways logo]()
$888
Last-minute flights from Portland to StewartDiscover last-minute flight deals from Portland to Stewart. Data last updated October 26, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Stewart. Data last updated October 26, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 10/275:09 pm -
1 stop18h 30m
Fri 10/305:39 pm -
2 stops22h 45m
Deal found 10/21![Multiple Airlines logo]()
$616
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 10/289:48 am -
1 stop24h 28m
Sat 10/3112:39 pm -
2 stops21h 42m
Deal found 10/21![Breeze Airways logo]()
$571
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 10/319:48 am -
1 stop25h 28m
Wed 11/412:39 pm -
2 stops20h 42m
Deal found 10/24![Breeze Airways logo]()
$595
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/35:09 pm -
1 stop18h 30m
Sat 11/712:39 pm -
2 stops20h 42m
Deal found 10/21![Breeze Airways logo]()
$424
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/35:09 pm -
1 stop18h 30m
Mon 11/95:49 pm -
2 stops39h 19m
Deal found 10/21![Multiple Airlines logo]()
$445
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/35:09 pm -
1 stop18h 30m
Sun 11/810:56 am -
1 stop22h 12m
Deal found 10/21![Breeze Airways logo]()
$447
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/35:09 pm -
1 stop18h 30m
Thu 11/510:56 am -
1 stop22h 12m
Deal found 10/21![Breeze Airways logo]()
$545
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/63:53 pm -
2 stops19h 46m
Sun 11/810:56 am -
1 stop22h 12m
Deal found 10/21![Breeze Airways logo]()
$605
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/76:31 pm -
2 stops16h 39m
Thu 11/1210:56 am -
1 stop22h 12m
Deal found 10/23![Multiple Airlines logo]()
$543
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/105:09 pm -
1 stop18h 30m
Thu 11/1210:56 am -
1 stop22h 12m
Deal found 10/25![Breeze Airways logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/115:09 pm -
2 stops17h 07m
Fri 11/135:30 pm -
1 stop15h 38m
Deal found 10/23![Multiple Airlines logo]()
$489
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 October 26, 2026.
Search for one-way flight options from Portland to Stewart. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/105:09 pm -
1 stop18h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Breeze Airways logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/35:09 pm -
1 stop18h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Breeze Airways logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/133:53 pm -
2 stops19h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Breeze Airways logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 1/185:00 pm -
3 stops42h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Breeze Airways logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 12/75:35 pm -
3 stops42h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 3/206:31 pm -
2 stops14h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/1711:31 am -
2 stops24h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Breeze Airways logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 10/315:09 pm -
2 stops18h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Breeze Airways logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/115:09 pm -
2 stops17h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/175:09 pm -
3 stops41h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$247
Find flight deals from Portland to Stewart
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) 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 October 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $364 (Kiwi.com) |
One-way from | $162 (Kiwi.com) |
Popular in | August |
Cheapest in | May |
Average price | $320 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Stewart 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 October 26, 2026.
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
Cheapest round-trip
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Mon 1/11
5:00 pm-11:39 am
3 stops42h 39m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$196
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Sat 10/31
5:09 pm-11:16 am
2 stops18h 07m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$235
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Wed 11/11
5:09 pm-10:16 am
2 stops17h 07m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$235
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Tue 12/15
10:01 am-11:39 am
2 stops25h 38m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$278
Quickest round-trip
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Sat 11/14
6:31 pm-11:10 am
2 stops16h 39m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Sat 12/19
9:48 am-10:26 am
1 stop24h 38m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$317
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Fri 11/6
3:53 pm-11:39 am
2 stops19h 46m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$317
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Sun 2/7
10:01 am-10:57 am
3 stops24h 56m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$317
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Wed 12/2
7:12 pm-9:48 am
1 stop14h 36m
New Windsor Stewart
Fri 12/4
11:03 am-9:08 am
1 stop22h 05m
$413
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Thu 11/5
3:10 pm-11:36 am
2 stops20h 26m
New Windsor Stewart
Sun 11/8
10:56 am-9:08 am
1 stop22h 12m
$740
Showing 1-10 of 16 resultsSorted by cheapest first
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.
PWM-SWF
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 Portland to Stewart. 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 New Windsor?
Book flights to New Windsor if you plan to visit one of these locationsKingston
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