$180+ Cheap flights from New Windsor to Portland, ME (SWF - PWM)
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.
SWF — PWM
Nov 24 — Dec 11
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
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Last-minute
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Cheapest flights from Stewart to PortlandExplore the most affordable flight options available from Stewart to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
Explore the most affordable flight options available from Stewart to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 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 11/1112:39 pm -
2 stops20h 42m
Tue 11/175:09 pm -
1 stop18h 30m
Deal found 10/22![Breeze Airways logo]()
$355
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 11/712:39 pm -
2 stops20h 42m
Tue 11/105:09 pm -
1 stop18h 30m
Deal found 10/24![Breeze Airways logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/1412:39 pm -
2 stops20h 42m
Tue 11/175:09 pm -
1 stop18h 30m
Deal found 10/19![Breeze Airways logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/1910:56 am -
1 stop22h 12m
Wed 12/212:28 pm -
2 stops29h 31m
Deal found 10/20![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/1910:56 am -
1 stop22h 12m
Tue 12/15:09 pm -
1 stop18h 30m
Deal found 10/20![Breeze Airways logo]()
$452
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 -
1 stop22h 02m
Wed 12/97:12 pm -
1 stop14h 36m
Deal found 10/20![Multiple Airlines logo]()
$453
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.
Fri 11/612:16 pm -
2 stops29h 35m
Tue 11/105:09 pm -
1 stop18h 30m
Deal found 10/23![Breeze Airways logo]()
$457
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/810:56 am -
1 stop22h 12m
Tue 11/105:09 pm -
1 stop18h 30m
Deal found 10/19![Breeze Airways logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/2210:56 am -
1 stop22h 12m
Wed 12/212:28 pm -
2 stops29h 31m
Deal found 10/20![Multiple Airlines logo]()
$464
Best flights from Stewart to PortlandDiscover carefully curated flight deals from Stewart to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
Discover carefully curated flight deals from Stewart to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
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 11/712:39 pm -
2 stops20h 42m
Tue 11/105:09 pm -
1 stop18h 30m
Deal found 10/24![Breeze Airways logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/2210:56 am -
1 stop22h 12m
Wed 12/212:28 pm -
2 stops29h 31m
Deal found 10/20![Multiple Airlines logo]()
$464
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.
Sun 12/611:06 am -
1 stop22h 02m
Wed 12/97:12 pm -
1 stop14h 36m
Deal found 10/21![Multiple Airlines logo]()
$469
This Booking.com deal was found by Cheapflights users on 10/20. 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.
Sun 11/1510:56 am -
1 stop22h 12m
Wed 11/189:48 am -
1 stop24h 28m
Deal found 10/20![Breeze Airways logo]()
$768
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:39 pm -
2 stops20h 42m
Fri 11/133:53 pm -
2 stops19h 46m
Deal found 10/23![Breeze Airways logo]()
$798
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/710:56 am -
1 stop22h 12m
Fri 1/85:00 pm -
3 stops18h 39m
Deal found 10/23![Breeze Airways logo]()
$819
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 11/712:39 pm -
2 stops20h 42m
Wed 11/119:48 am -
1 stop24h 28m
Deal found 10/24![Breeze Airways logo]()
$833
This Booking.com deal was found by Cheapflights users on 10/20. 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.
Thu 1/710:56 am -
1 stop22h 12m
Sat 1/99:48 am -
1 stop24h 28m
Deal found 10/20![Breeze Airways logo]()
$838
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1112:16 pm -
2 stops20h 52m
Sun 12/1310:31 am -
2 stops25h 05m
Deal found 10/23![Breeze Airways logo]()
$858
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.
Thu 11/1910:56 am -
1 stop22h 12m
Fri 11/205:35 pm -
3 stops18h 04m
Deal found 10/21![Breeze Airways logo]()
$899
This KAYAK deal was found by Cheapflights users on 10/20. 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.
Wed 12/912:39 pm -
2 stops21h 12m
Sun 12/1310:31 am -
2 stops25h 05m
Deal found 10/20![Breeze Airways logo]()
$938
Last-minute flights from Stewart to PortlandDiscover last-minute flight deals from Stewart to Portland. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Portland. Data last updated October 25, 2026 and is based on user searches.
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.
Fri 11/612:16 pm -
2 stops29h 35m
Tue 11/105:09 pm -
1 stop18h 30m
Deal found 10/23![Breeze Airways logo]()
$457
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 11/712:39 pm -
2 stops20h 42m
Tue 11/105:09 pm -
1 stop18h 30m
Deal found 10/24![Breeze Airways logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/810:56 am -
1 stop22h 12m
Tue 11/105:09 pm -
1 stop18h 30m
Deal found 10/19![Breeze Airways logo]()
$463
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 11/1112:39 pm -
2 stops20h 42m
Tue 11/175:09 pm -
1 stop18h 30m
Deal found 10/22![Breeze Airways logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/1412:39 pm -
2 stops20h 42m
Tue 11/175:09 pm -
1 stop18h 30m
Deal found 10/19![Breeze Airways logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/1910:56 am -
1 stop22h 12m
Wed 12/212:28 pm -
2 stops29h 31m
Deal found 10/20![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/1910:56 am -
1 stop22h 12m
Tue 12/15:09 pm -
1 stop18h 30m
Deal found 10/20![Breeze Airways logo]()
$452
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/2210:56 am -
1 stop22h 12m
Wed 12/212:28 pm -
2 stops29h 31m
Deal found 10/20![Multiple Airlines logo]()
$464
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/2210:56 am -
1 stop22h 12m
Tue 12/15:09 pm -
1 stop18h 30m
Deal found 10/20![Breeze Airways logo]()
$479
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 25, 2026.
Search for one-way flight options from Stewart to Portland. Find affordable one-way fares based on user searches. Data last updated October 25, 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.
Mon 11/167:04 pm -
3 stops45h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$180
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.
Thu 11/1210:56 am -
1 stop22h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Breeze Airways logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/1512:00 pm -
3 stops52h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$215
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 11/1812:39 pm -
3 stops25h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Breeze Airways logo]()
$220
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 11/97:04 pm -
2 stops21h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$233
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 11/912:16 pm -
3 stops28h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Breeze Airways logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 10/3112:39 pm -
2 stops21h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Breeze Airways logo]()
$243
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 11/65:30 pm -
1 stop15h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$246
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 (PWM). 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 25, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $355 (Kiwi.com) |
One-way from | $180 (Kiwi.com) |
Popular in | September |
Cheapest in | May |
Average price | $338 |
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 October 25, 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 - PWM Portland
SWFPWM
New Windsor Stewart
Mon 11/9
12:16 pm-4:24 pm
3 stops28h 08m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
New WindsorPortland
SWF New Windsor Stewart - PWM Portland
SWFPWM
New Windsor Stewart
Fri 11/6
5:30 pm-9:08 am
1 stop15h 38m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$246
New WindsorPortland
SWF New Windsor Stewart - PWM Portland
SWFPWM
New Windsor Stewart
Fri 11/20
11:29 am-9:08 am
1 stop21h 39m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$266
New WindsorPortland
SWF New Windsor Stewart - PWM Portland
SWFPWM
New Windsor Stewart
Sat 10/31
12:39 pm-10:21 am
2 stops21h 42m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$282
New WindsorPortland
SWF New Windsor Stewart - PWM Portland
SWFPWM
New Windsor Stewart
Sun 11/8
10:56 am-9:08 am
1 stop22h 12m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$294
New WindsorPortland
SWF New Windsor Stewart - PWM Portland
SWFPWM
New Windsor Stewart
Sat 1/2
12:39 pm-9:08 am
2 stops44h 29m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$303
New WindsorPortland
SWF New Windsor Stewart - PWM Portland
SWFPWM
New Windsor Stewart
Thu 11/12
10:56 am-4:55 pm
2 stops29h 59m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$326
New WindsorPortland
SWF New Windsor Stewart - PWM Portland
SWFPWM
New Windsor Stewart
Sun 11/15
5:37 pm-4:55 pm
2 stops23h 18m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$356
New WindsorPortland
SWF New Windsor Stewart - PWM Portland
SWFPWM
New Windsor Stewart
Tue 11/24
10:59 am-4:24 pm
2 stops29h 25m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$361
New WindsorPortland
SWF New Windsor Stewart - PWM Portland
SWFPWM
New Windsor Stewart
Fri 10/30
12:16 pm-4:24 pm
3 stops28h 08m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$390
Showing 1-10 of 22 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on New Windsor-Portland, Maine 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, Maine flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from New Windsor-Portland, Maine flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on New Windsor-Portland, Maine 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, Maine 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-PWM
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 locationsLewiston
North Conway
Brunswick
Conway
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