$146+ Cheap flights from Islip, NY to Portland, ME (ISP - 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — PWM
Oct 10 — Oct 171
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Islip 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 Islip to Portland
Cheapest
Best
Last-minute
One-way
Cheapest flights from Islip to PortlandExplore the most affordable flight options available from Islip to Portland. 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 Islip to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:40 pm -
1 stop6h 15m
Mon 10/265:20 am -
1 stop6h 25m
Deal found 9/8![Southwest logo]()
$279
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 11/312:00 pm -
1 stop28h 24m
Tue 11/105:09 pm -
1 stop18h 11m
Deal found 9/7![Breeze Airways logo]()
$281
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:40 pm -
1 stop6h 15m
Wed 10/75:40 am -
1 stop10h 05m
Deal found 9/9![Southwest logo]()
$284
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:05 am -
2 stops11h 15m
Thu 10/296:30 am -
2 stops10h 30m
Deal found 9/8![Southwest logo]()
$289
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:40 am -
1 stop5h 50m
Fri 10/305:20 am -
1 stop6h 25m
Deal found 9/9![Southwest logo]()
$299
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:00 am -
2 stops10h 30m
Thu 11/1211:10 am -
2 stops11h 35m
Deal found 9/8![Southwest logo]()
$319
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:25 pm -
1 stop4h 05m
Sun 11/85:10 pm -
1 stop6h 20m
Deal found 9/9![Southwest logo]()
$338
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:05 am -
1 stop3h 45m
Tue 11/105:15 am -
1 stop6h 30m
Deal found 9/7![Southwest logo]()
$339
Best flights from Islip to PortlandDiscover carefully curated flight deals from Islip to Portland 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 Islip to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:05 am -
1 stop6h 15m
Thu 10/295:20 am -
1 stop6h 25m
Deal found 9/8![Southwest logo]()
$279
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 10/96:55 pm -
1 stop14h 13m
Mon 10/123:53 pm -
2 stops19h 27m
Deal found 9/6![Multiple Airlines logo]()
$512
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:40 am -
1 stop5h 50m
Fri 10/305:20 am -
1 stop6h 25m
Deal found 9/9![Southwest logo]()
$299
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:25 pm -
1 stop4h 05m
Sun 11/85:10 pm -
1 stop6h 20m
Deal found 9/9![Southwest logo]()
$338
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:30 am -
2 stops8h 15m
Tue 11/1010:25 am -
2 stops10h 40m
Deal found 9/7![Southwest logo]()
$388
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:00 am -
2 stops10h 55m
Mon 10/266:30 am -
2 stops10h 30m
Deal found 9/8![Southwest logo]()
$447
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:40 pm -
1 stop6h 15m
Mon 10/195:20 am -
1 stop9h 10m
Deal found 9/9![Southwest logo]()
$450
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2210:55 am -
2 stops11h 15m
Sat 9/265:40 am -
1 stop6h 25m
Deal found 9/7![Southwest logo]()
$474
Last-minute flights from Islip to PortlandDiscover last-minute flight deals from Islip to Portland. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Islip to Portland. Data last updated September 10, 2026 and is based on user searches.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/284:05 pm -
1 stop6h 25m
Wed 9/305:45 am -
1 stop4h 30m
Deal found 9/8![Southwest logo]()
$374
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:40 pm -
1 stop6h 15m
Wed 10/75:40 am -
1 stop10h 05m
Deal found 9/9![Southwest logo]()
$284
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:40 pm -
1 stop6h 15m
Mon 10/265:20 am -
1 stop6h 25m
Deal found 9/8![Southwest logo]()
$279
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:40 pm -
1 stop6h 15m
Sun 10/255:40 am -
1 stop4h 40m
Deal found 9/9![Southwest logo]()
$408
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:05 am -
2 stops11h 15m
Thu 10/296:30 am -
2 stops10h 30m
Deal found 9/8![Southwest logo]()
$289
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:40 am -
1 stop5h 50m
Fri 10/305:20 am -
1 stop6h 25m
Deal found 9/9![Southwest logo]()
$299
One-way flights from Islip to PortlandSearch for one-way flight options from Islip to Portland. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
Search for one-way flight options from Islip 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 9/7. 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 10/2012:00 pm -
1 stop28h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Breeze Airways logo]()
$146
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:40 am -
1 stop4h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$179
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.
Sun 10/256:25 pm -
2 stops22h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$255
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.
Mon 9/1411:52 am -
1 stop28h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Breeze Airways logo]()
$256
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.
Thu 9/175:43 pm -
1 stop15h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$291
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 9/135:43 pm -
1 stop15h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$321
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.
Mon 9/145:43 pm -
2 stops22h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$325
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.
Thu 9/177:45 pm -
2 stops21h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Breeze Airways logo]()
$343
Find flight deals from Islip to Portland
Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) 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 September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $279 (Southwest) |
One-way from | $146 (Kiwi.com) |
Popular in | March |
Cheapest in | May |
Average price | $300 |
Cheapflights Fare Finder
Customize your flight search to find flights from Islip 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 Islip to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
IslipPortland
ISP Islip Long Island - PWM Portland
ISPPWM
Islip Long Island
Tue 10/20
1:38 pm-9:08 am
2 stops19h 30m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$164
Quickest round-trip
IslipPortland
ISP Islip Long Island - PWM Portland
ISPPWM
Islip Long Island
Sun 10/25
5:40 am-9:40 am
1 stop4h 00m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
IslipPortland
ISP Islip Long Island - PWM Portland
ISPPWM
Islip Long Island
Sun 10/25
6:25 pm-4:55 pm
2 stops22h 30m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$255
IslipPortland
ISP Islip Long Island - PWM Portland
ISPPWM
Islip Long Island
Mon 9/14
11:52 am-4:24 pm
1 stop28h 32m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$256
IslipPortland
ISP Islip Long Island - PWM Portland
ISPPWM
Islip Long Island
Tue 10/27
6:05 am-12:20 pm
1 stop6h 15m
Portland
Thu 10/29
5:20 am-11:45 am
1 stop6h 25m
$279
IslipPortland
ISP Islip Long Island - PWM Portland
ISPPWM
Islip Long Island
Tue 10/27
9:40 am-3:30 pm
1 stop5h 50m
Portland
Fri 10/30
5:20 am-11:45 am
1 stop6h 25m
$299
IslipPortland
ISP Islip Long Island - PWM Portland
ISPPWM
Islip Long Island
Mon 9/14
5:43 pm-4:24 pm
2 stops22h 41m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$325
IslipPortland
ISP Islip Long Island - PWM Portland
ISPPWM
Islip Long Island
Fri 11/6
12:25 pm-4:30 pm
1 stop4h 05m
Portland
Sun 11/8
5:10 pm-11:30 pm
1 stop6h 20m
$338
IslipPortland
ISP Islip Long Island - PWM Portland
ISPPWM
Islip Long Island
Wed 9/23
12:00 pm-4:24 pm
1 stop4h 24m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$354
IslipPortland
ISP Islip Long Island - PWM Portland
ISPPWM
Islip Long Island
Sun 9/13
7:45 pm-4:55 pm
2 stops21h 10m
Portland
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$361
Showing 1-10 of 18 resultsSorted by cheapest first
Compare providers for flights from Islip to Portland
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Islip to Portland in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Islip, New York-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Islip, New York-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Islip, New York-Portland, Maine flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Islip, New York-Portland, Maine flights, Cheapflights users trust FlightHub the most. FlightHub 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 Islip, New York-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 Islip to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Islip with our price prediction graph.
ISP-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 Islip 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 locationsNorth Conway
Lewiston
Brunswick
Conway
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Islip
Popular flights
Portland flight routes