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$308+ Cheap flights from Portland, ME to Islip (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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ISP
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$406
(Kiwi.com)

One-way from

$308
(KAYAK)

Popular in

February

Cheapest in

September

Average price

$146
From Portland to Islip Long Island
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One-way flight from Portland to Islip Long Island
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Highest demand for flights based on searches. 17% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/269:46 amPWM - ISP
1 stop25h 09mMultiple Airlines
Tue 9/3011:25 amISP - PWM
1 stop23h 21mMultiple Airlines
Deal found 9/11$406
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/255:50 amPWM - ISP
1 stop6h 10mSouthwest
Fri 9/263:05 pmISP - PWM
1 stop4h 55mSouthwest
Deal found 9/10$526
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/129:46 amPWM - ISP
1 stop25h 09mMultiple Airlines
Sun 9/1411:25 amISP - PWM
1 stop21h 41mMultiple Airlines
Deal found 9/11$660
This Southwest deal was found by Cheapflights users on 9/11. 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 9/123:30 pmPWM - ISP
2 stops7h 25mSouthwest
Sun 9/147:45 amISP - PWM
2 stops11h 25mSouthwest
Deal found 9/11$697
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/262:36 pmPWM - ISP
3 stops28h 16mBreeze Airways
Mon 9/297:08 pmISP - PWM
1 stop17h 10mBreeze Airways
Deal found 9/10$722

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 September 11, 2025.
Use the filters below to find and compare flights from Portland to Islip that are best for you.

Fly from

Portland

Fly to

Islip

Route

Depart

Return

Price

PortlandIslip

PWM - ISP

PWMISP

Portland

Fri 9/26

9:46 am-10:55 am

1 stop25h 09m

Islip Long Island

Tue 9/30

11:25 am-10:46 am

1 stop23h 21m

$406

PortlandIslip

PWM - ISP

PWMISP

Portland

Thu 9/25

5:50 am-12:00 pm

1 stop6h 10m

Islip Long Island

Fri 9/26

3:05 pm-8:00 pm

1 stop4h 55m

$526

PortlandIslip

PWM - ISP

PWMISP

Portland

Wed 2/25

6:18 pm-11:05 am

2 stops16h 47m

Islip Long Island

Sat 2/28

6:49 pm-11:21 am

1 stop16h 32m

$658

PortlandIslip

PWM - ISP

PWMISP

Portland

Fri 9/26

2:36 pm-6:52 pm

3 stops28h 16m

Islip Long Island

Mon 9/29

7:08 pm-12:18 pm

1 stop17h 10m

$722

PortlandIslip

PWM - ISP

PWMISP

Portland

Wed 9/17

4:41 pm-6:56 pm

1 stop26h 15m

$308

PortlandIslip

PWM - ISP

PWMISP

Portland

Thu 9/18

5:40 pm-6:28 pm

1 stop24h 48m

$324

PortlandIslip

PWM - ISP

PWMISP

Portland

Mon 10/13

5:45 am-2:35 pm

2 stops8h 50m

$335

PortlandIslip

PWM - ISP

PWMISP

Portland

Sun 10/12

5:40 pm-6:28 pm

1 stop24h 48m

$467

PortlandIslip

PWM - ISP

PWMISP

Portland

Mon 10/13

2:36 pm-9:58 am

3 stops19h 22m

$527

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

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.

Cheapflights Insights

Everything you need to know about your flight from Portland to Islip

What is the cheapest month to book a flight from Portland, Maine to Islip?

Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Islip (average of $108). Flying from Portland, Maine to Islip in November is currently the most expensive (average of $213). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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?

    Airlines like Southwest fly from Portland, Maine to Islip in about 6h 10m. The time it takes to get you to your destination can typically vary by up to . The distance between Portland, Maine and Islip 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.

  • What is the cheapest month to book a flight from Portland, Maine to Islip?

    Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Islip (average of $108). Flying from Portland, Maine to Islip in November is currently the most expensive (average of $213). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Islip?

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

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