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$244+ 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ISP
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$331
(Kiwi.com)

One-way from

$244
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$196
Provider with most accurate pricing for Portland-Islip Long Island flight deals.
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Provider most trusted by Cheapflights users for Portland-Islip Long Island flights.
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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. 14% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/109:46 amPWM - ISP
1 stop9h 20mMultiple Airlines
Fri 11/144:58 pmISP - PWM
1 stop17h 38mMultiple Airlines
Deal found 10/26$331
This Southwest deal was found by Cheapflights users on 10/25. 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 11/65:25 pmPWM - ISP
1 stop6h 25mSouthwest
Mon 11/105:50 amISP - PWM
1 stop5h 20mSouthwest
Deal found 10/25$482
This Gotogate deal was found by Cheapflights users on 10/26. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/102:36 pmPWM - ISP
3 stops19h 22mBreeze Airways
Fri 11/147:08 pmISP - PWM
2 stops15h 33mBreeze Airways
Deal found 10/26$729
This FlightHub deal was found by Cheapflights users on 10/28. 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.
Thu 11/2010:49 amPWM - ISP
1 stop7h 06mBreeze Airways
Sun 11/2311:40 amISP - PWM
2 stops21h 26mBreeze Airways
Deal found 10/28$769
This FlightHub deal was found by Cheapflights users on 10/26. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:40 pmPWM - ISP
1 stop24h 48mBreeze Airways
Mon 11/107:08 pmISP - PWM
1 stop22h 41mBreeze Airways
Deal found 10/26$792

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 October 28, 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

Mon 11/10

9:46 am-7:06 pm

1 stop9h 20m

Islip Long Island

Fri 11/14

4:58 pm-10:36 am

1 stop17h 38m

$331

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

$612

PortlandIslip

PWM - ISP

PWMISP

Portland

Mon 11/10

2:36 pm-9:58 am

3 stops19h 22m

Islip Long Island

Fri 11/14

7:08 pm-10:41 am

2 stops15h 33m

$729

PortlandIslip

PWM - ISP

PWMISP

Portland

Thu 11/20

10:49 am-5:55 pm

1 stop7h 06m

Islip Long Island

Sun 11/23

11:40 am-9:06 am

2 stops21h 26m

$769

PortlandIslip

PWM - ISP

PWMISP

Portland

Tue 11/25

11:50 am-11:10 pm

2 stops11h 20m

Islip Long Island

Sat 11/29

5:30 am-11:40 am

1 stop6h 10m

$907

PortlandIslip

PWM - ISP

PWMISP

Portland

Thu 11/6

3:15 pm-8:07 pm

3 stops28h 52m

$244

PortlandIslip

PWM - ISP

PWMISP

Portland

Thu 11/6

5:25 pm-11:50 pm

1 stop6h 25m

$269

PortlandIslip

PWM - ISP

PWMISP

Portland

Thu 11/6

5:40 pm-8:07 pm

2 stops26h 27m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland, Maine-Islip, New York flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

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, New York?

Currently, October is the cheapest month in which you can book a flight from Portland, Maine to Islip, New York (average of $55). Flying from Portland, Maine to Islip, New York in February is currently the most expensive (average of $117). 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, New York?

    There are many flights that can get you from Portland, Maine to Islip, New York in 16h 47m. Fly via Breeze Airways 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.

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

    Currently, October is the cheapest month in which you can book a flight from Portland, Maine to Islip, New York (average of $55). Flying from Portland, Maine to Islip, New York in February is currently the most expensive (average of $117). 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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