HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$137+ Cheap flights from Islip, NY to Portland, ME (ISP - PWM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — PWM
Aug 23 — Aug 301
Sun 8/23
Sun 8/30
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 flights from Islip to Portland
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 July 24, 2026.

This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:10 am
ISP
-
PWM
1 stop3h 40m
Southwest
Thu 9/175:55 am
PWM
-
ISP
1 stop3h 45m
Southwest
Deal found 7/21$273
This Southwest deal was found by Cheapflights users on 7/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:05 pm
ISP
-
PWM
1 stop6h 25m
Southwest
Sat 9/125:40 am
PWM
-
ISP
1 stop6h 25m
Southwest
Deal found 7/23$278
This Southwest deal was found by Cheapflights users on 7/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:05 am
ISP
-
PWM
1 stop3h 50m
Southwest
Sat 9/125:40 am
PWM
-
ISP
1 stop6h 25m
Southwest
Deal found 7/24$279
This Southwest deal was found by Cheapflights users on 7/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:05 am
ISP
-
PWM
1 stop3h 50m
Southwest
Tue 8/255:45 am
PWM
-
ISP
1 stop4h 30m
Southwest
Deal found 7/20$289
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/214:05 pm
ISP
-
PWM
1 stop6h 20m
Southwest
Tue 8/255:45 am
PWM
-
ISP
1 stop4h 30m
Southwest
Deal found 7/21$310
This Southwest deal was found by Cheapflights users on 7/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:05 am
ISP
-
PWM
1 stop3h 50m
Southwest
Sat 8/227:25 am
PWM
-
ISP
1 stop4h 40m
Southwest
Deal found 7/20$318

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 July 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$273
(Southwest)

One-way from

$137
(Southwest)

Popular in

March

Cheapest in

September

Average price

$296
Provider with most accurate pricing for Islip Long Island-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Islip Long Island-Portland flights.
Search Deals
From Islip Long Island to Portland
Search Deals
One-way flight from Islip Long Island to Portland
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 2,558,603 searches. Data last updated July 24, 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

Price

Cheapest round-trip
Quickest round-trip

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Mon 9/14

6:10 am-9:50 am

1 stop3h 40m

Portland

Thu 9/17

5:55 am-9:40 am

1 stop3h 45m

$273

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 9/11

4:05 pm-10:30 pm

1 stop6h 25m

Portland

Sat 9/12

5:40 am-12:05 pm

1 stop6h 25m

$278

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Tue 9/8

6:05 am-9:55 am

1 stop3h 50m

Portland

Sat 9/12

5:40 am-12:05 pm

1 stop6h 25m

$279

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Wed 8/19

6:05 am-9:55 am

1 stop3h 50m

Portland

Tue 8/25

5:45 am-10:15 am

1 stop4h 30m

$289

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 8/21

4:05 pm-10:25 pm

1 stop6h 20m

Portland

Tue 8/25

5:45 am-10:15 am

1 stop4h 30m

$310

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Thu 10/15

5:40 pm-11:55 pm

1 stop6h 15m

Portland

Sun 10/18

5:40 am-10:20 am

1 stop4h 40m

$315

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Wed 8/19

6:05 am-9:55 am

1 stop3h 50m

Portland

Sat 8/22

7:25 am-12:05 pm

1 stop4h 40m

$318
Cheapest one-way
Quickest one-way

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Wed 8/19

3:20 pm-9:10 pm

1 stop5h 50m

$137

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Tue 8/11

12:55 pm-10:05 pm

2 stops9h 10m

$150

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Sun 8/16

6:20 am-4:35 pm

2 stops10h 15m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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.

  • How long is the flight from Islip, New York to Portland, Maine?

    For as low as $273, Southwest can have you in Portland, Maine from Islip, New York in 3h 40m. There are 243 mi between Islip, New York and Portland, Maine.

  • Can I find deals for flights from Islip to Portland that include hotel bookings?

    Yes. In addition to deals on Islip to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Islip to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Islip to Portland.

  • Can I find deals for business class flights from Islip to Portland?

    Yes. Cheapflights offers flight deals from Islip to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights