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Islip

$140+ Cheap flights from Portland, ME to Islip, NY (PWM - ISP)

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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ISP
Aug 27 — Sep 31
Thu 8/27
Thu 9/3
1 adult, Economy
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Cheap flight deals from Portland to Islip

Cheapest flights from Portland to Islip
Explore the most affordable flight options available from Portland to Islip. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2026.

This Southwest deal was found by Cheapflights users on 7/27. 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 9/35:55 am
PWM
-
ISP
1 stop3h 45m
Southwest
Tue 9/83:20 pm
ISP
-
PWM
1 stop5h 55m
Southwest
Deal found 7/27$279
This Southwest deal was found by Cheapflights users on 7/27. 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 8/215:55 am
PWM
-
ISP
1 stop3h 45m
Southwest
Mon 8/244:05 pm
ISP
-
PWM
1 stop6h 20m
Southwest
Deal found 7/27$304
This Southwest deal was found by Cheapflights users on 7/27. 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 9/295:45 am
PWM
-
ISP
2 stops9h 10m
Southwest
Fri 10/25:40 pm
ISP
-
PWM
1 stop6h 15m
Southwest
Deal found 7/27$309
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.
Thu 9/243:40 pm
PWM
-
ISP
1 stop6h 30m
Southwest
Sun 9/274:35 pm
ISP
-
PWM
1 stop6h 25m
Southwest
Deal found 7/24$318
This Southwest deal was found by Cheapflights users on 7/26. 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 9/115:55 am
PWM
-
ISP
1 stop3h 45m
Southwest
Sun 9/134:35 pm
ISP
-
PWM
1 stop6h 25m
Southwest
Deal found 7/26$320
This Southwest deal was found by Cheapflights users on 7/27. 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 8/215:55 am
PWM
-
ISP
1 stop3h 45m
Southwest
Sun 8/2310:20 am
ISP
-
PWM
1 stop5h 20m
Southwest
Deal found 7/27$363

Find flight deals from Portland to Islip

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Islip (ISP). 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 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$279
(Southwest)

One-way from

$140
(Southwest)

Popular in

March

Cheapest in

October

Average price

$250
Provider with most accurate pricing for Portland-Islip Long Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Islip Long Island flights.
Search Deals
From Portland to Islip Long Island
Search Deals
One-way flight from Portland to Islip Long Island
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 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 Portland to Islip 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 28, 2026.
Use the filters below to find and compare flights from Portland to Islip that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

PortlandIslip

PWM - ISP

PWMISP

Portland

Thu 9/3

5:55 am-9:40 am

1 stop3h 45m

Islip Long Island

Tue 9/8

3:20 pm-9:15 pm

1 stop5h 55m

$279

PortlandIslip

PWM - ISP

PWMISP

Portland

Tue 9/29

5:45 am-2:55 pm

2 stops9h 10m

Islip Long Island

Fri 10/2

5:40 pm-11:55 pm

1 stop6h 15m

$309

PortlandIslip

PWM - ISP

PWMISP

Portland

Thu 9/24

3:40 pm-10:10 pm

1 stop6h 30m

Islip Long Island

Sun 9/27

4:35 pm-11:00 pm

1 stop6h 25m

$318

PortlandIslip

PWM - ISP

PWMISP

Portland

Fri 9/11

5:55 am-9:40 am

1 stop3h 45m

Islip Long Island

Sun 9/13

4:35 pm-11:00 pm

1 stop6h 25m

$320

PortlandIslip

PWM - ISP

PWMISP

Portland

Fri 8/21

10:30 am-9:30 pm

2 stops11h 00m

Islip Long Island

Mon 8/24

4:05 pm-10:25 pm

1 stop6h 20m

$364

PortlandIslip

PWM - ISP

PWMISP

Portland

Mon 8/24

7:40 am-4:25 pm

2 stops8h 45m

Islip Long Island

Fri 8/28

4:05 pm-10:25 pm

1 stop6h 20m

$404

PortlandIslip

PWM - ISP

PWMISP

Portland

Wed 8/26

11:07 am-9:53 am

1 stop22h 46m

Islip Long Island

Sun 8/30

7:09 pm-9:12 am

1 stop14h 03m

$526
Cheapest one-way
Quickest one-way

PortlandIslip

PWM - ISP

PWMISP

Portland

Thu 8/20

5:55 am-9:40 am

1 stop3h 45m

$140

PortlandIslip

PWM - ISP

PWMISP

Portland

Fri 12/18

10:30 am-4:20 pm

1 stop5h 50m

$199

PortlandIslip

PWM - ISP

PWMISP

Portland

Fri 8/14

5:55 am-9:40 am

1 stop3h 45m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

Compare providers for flights from Portland to Islip

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 Portland to Islip 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 Portland, Maine-Islip, New York flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Islip, New York flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Islip, New York flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-Islip, New York 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 Portland, Maine-Islip, New York 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 Portland to Islip

Have a flexible travel schedule? Discover the best time to fly to Islip from Portland 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 Portland to Islip. 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 Portland, Maine to Islip, New York?

    There are many flights that can get you from Portland, Maine to Islip, New York in 3h 45m. Fly via Southwest to get the fastest option. The distance between Portland, Maine and Islip, New York is about 243 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland to Islip 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 Islip?

Book flights to Islip if you plan to visit one of these locations
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