$159+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SWF
Oct 10 — Oct 171
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
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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
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Best
Last-minute
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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 September 10, 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 September 10, 2026.
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.
Sun 11/13:10 pm -
2 stops20h 26m
Thu 11/510:56 am -
1 stop22h 12m
Deal found 9/6![Breeze Airways logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 11/13:10 pm -
2 stops20h 26m
Fri 11/65:30 pm -
1 stop15h 38m
Deal found 9/10![Multiple Airlines logo]()
$441
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.
Tue 10/65:09 pm -
1 stop18h 30m
Sat 10/1012:39 pm -
2 stops20h 42m
Deal found 9/7![Breeze Airways logo]()
$471
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.
Sat 9/266:31 pm -
1 stop15h 52m
Mon 9/2811:21 am -
2 stops29h 03m
Deal found 9/7![Multiple Airlines logo]()
$474
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.
Tue 9/225:09 pm -
1 stop18h 30m
Sat 9/2612:39 pm -
2 stops20h 42m
Deal found 9/7![Breeze Airways logo]()
$496
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 12/97:12 pm -
1 stop14h 36m
Thu 12/1711:06 am -
1 stop22h 02m
Deal found 9/9![Multiple Airlines logo]()
$498
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.
Wed 9/306:31 pm -
2 stops15h 07m
Sun 10/410:56 am -
1 stop22h 12m
Deal found 9/6![Multiple Airlines logo]()
$502
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.
Wed 10/146:31 pm -
2 stops14h 57m
Fri 10/168:48 pm -
1 stop12h 20m
Deal found 9/8![Multiple Airlines logo]()
$520
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.
Wed 9/235:09 pm -
2 stops17h 07m
Fri 9/2510:48 am -
1 stop6h 07m
Deal found 9/7![Breeze Airways logo]()
$529
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.
Fri 9/253:53 pm -
2 stops19h 46m
Sun 9/2710:56 am -
1 stop22h 12m
Deal found 9/7![Breeze Airways logo]()
$537
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 September 10, 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 September 10, 2026.
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.
Sun 11/13:10 pm -
2 stops20h 26m
Thu 11/510:56 am -
1 stop22h 12m
Deal found 9/6![Breeze Airways logo]()
$422
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.
Tue 9/225:09 pm -
1 stop18h 30m
Sat 9/2612:39 pm -
2 stops20h 42m
Deal found 9/7![Breeze Airways logo]()
$496
This CheapOair 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 CheapOair 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 9/7![Breeze Airways logo]()
$624
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.
Tue 9/155:09 pm -
1 stop18h 30m
Thu 9/1710:56 am -
1 stop22h 12m
Deal found 9/8![Breeze Airways logo]()
$644
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:09 pm -
1 stop18h 30m
Thu 11/1910:56 am -
1 stop22h 12m
Deal found 9/10![Breeze Airways logo]()
$658
This Booking.com deal was found by Cheapflights users on 9/10. 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 10/163:53 pm -
2 stops19h 46m
Sun 10/1810:56 am -
1 stop22h 12m
Deal found 9/10![Breeze Airways logo]()
$664
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.
Sun 10/47:00 am -
2 stops28h 36m
Sun 10/1110:56 am -
1 stop22h 12m
Deal found 9/6![Breeze Airways logo]()
$665
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.
Fri 9/253:53 pm -
2 stops19h 46m
Sun 9/2710:56 am -
1 stop22h 12m
Deal found 9/8![Breeze Airways logo]()
$681
Last-minute flights from Portland to StewartDiscover last-minute flight deals from Portland to Stewart. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Stewart. Data last updated September 10, 2026 and is based on user searches.
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.
Wed 9/165:09 pm -
2 stops17h 07m
Fri 9/1811:06 am -
1 stop23h 22m
Deal found 9/8![Multiple Airlines logo]()
$588
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.
Tue 9/225:09 pm -
1 stop18h 30m
Sat 9/2612:39 pm -
2 stops20h 42m
Deal found 9/7![Breeze Airways logo]()
$496
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.
Wed 9/235:09 pm -
2 stops17h 07m
Fri 9/2510:48 am -
1 stop6h 07m
Deal found 9/7![Breeze Airways logo]()
$529
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.
Fri 9/253:53 pm -
2 stops19h 46m
Sun 9/2710:56 am -
1 stop22h 12m
Deal found 9/7![Breeze Airways logo]()
$537
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.
Sat 9/266:31 pm -
1 stop15h 52m
Mon 9/2811:21 am -
2 stops29h 03m
Deal found 9/7![Multiple Airlines logo]()
$474
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.
Tue 9/295:09 pm -
1 stop18h 30m
Thu 10/110:56 am -
1 stop22h 12m
Deal found 9/7![Breeze Airways logo]()
$556
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.
Wed 9/306:31 pm -
2 stops15h 07m
Sun 10/410:56 am -
1 stop22h 12m
Deal found 9/6![Multiple Airlines logo]()
$502
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.
Tue 10/65:09 pm -
1 stop18h 30m
Sat 10/1012:39 pm -
2 stops20h 42m
Deal found 9/7![Breeze Airways logo]()
$471
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.
Wed 10/79:48 am -
1 stop24h 28m
Sat 10/1012:39 pm -
2 stops8h 45m
Deal found 9/8![Breeze Airways logo]()
$555
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/135:09 pm -
1 stop18h 30m
Sat 10/1712:39 pm -
2 stops20h 42m
Deal found 9/10![Breeze Airways logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/135:09 pm -
1 stop18h 30m
Sun 10/1810:56 am -
1 stop22h 12m
Deal found 9/10![Breeze Airways logo]()
$595
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.
Wed 10/146:31 pm -
2 stops14h 57m
Fri 10/168:48 pm -
1 stop12h 20m
Deal found 9/8![Multiple Airlines logo]()
$520
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 9/8. 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.
Wed 10/286:31 pm -
2 stops15h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/303:53 pm -
2 stops19h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Breeze Airways logo]()
$161
This Kissandfly.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 Kissandfly.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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Breeze Airways logo]()
$168
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.
Fri 10/23:53 pm -
3 stops19h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Breeze Airways logo]()
$189
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.
Fri 11/133:53 pm -
2 stops19h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Breeze Airways logo]()
$197
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.
Fri 11/63:53 pm -
2 stops19h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Breeze Airways logo]()
$201
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.
Fri 10/233:53 pm -
2 stops19h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Breeze Airways logo]()
$207
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 September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $422 (Kiwi.com) |
One-way from | $159 (Kiwi.com) |
Popular in | March |
Cheapest in | October |
Average price | $248 |
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 September 10, 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
Fri 10/2
3:53 pm-11:39 am
3 stops19h 46m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
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
$201
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Wed 10/28
6:31 pm-4:09 pm
1 stop21h 38m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$224
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Tue 10/6
5:09 pm-11:39 am
1 stop18h 30m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$256
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Tue 10/27
11:31 am-11:39 am
2 stops24h 08m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$270
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Sat 9/26
7:00 am-10:16 am
3 stops27h 16m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$288
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Wed 10/7
9:48 am-10:16 am
1 stop24h 28m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$311
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Wed 10/7
7:00 am-10:16 am
2 stops27h 16m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$315
Quickest round-trip
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Sat 9/19
6:31 pm-10:23 am
1 stop15h 52m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$318
PortlandNew Windsor
PWM Portland - SWF New Windsor Stewart
PWMSWF
Portland
Thu 10/1
3:05 pm-11:36 am
2 stops20h 31m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$320
Showing 1-10 of 19 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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