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$337+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — PWM
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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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 December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Tue 12/168:29 pmISP - PWM
1 stop14h 07mMultiple Airlines
Thu 12/1811:58 amPWM - ISP
1 stop30h 30mMultiple Airlines
Deal found 12/9$441
This Southwest deal was found by Cheapflights users on 12/10. 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.
Mon 12/295:50 pmISP - PWM
1 stop6h 15mSouthwest
Thu 1/15:30 amPWM - ISP
1 stop6h 45mSouthwest
Deal found 12/10$443
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:20 pmISP - PWM
1 stop20h 46mMultiple Airlines
Mon 12/299:46 amPWM - ISP
1 stop25h 39mMultiple Airlines
Deal found 12/10$731
This Gotogate deal was found by Cheapflights users on 12/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:40 amISP - PWM
3 stops29h 45mBreeze Airways
Mon 12/299:46 amPWM - ISP
2 stops24h 12mBreeze Airways
Deal found 12/10$1,132

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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$337
(Southwest)

Popular in

April

Cheapest in

November

Average price

$223
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
Highest demand for flights based on searches. 3% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 12, 2025.
Use the filters below to find and compare flights from Islip to Portland that are best for you.

Fly from

Islip

Fly to

Portland

Route

Depart

Return

Price

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 1/30

6:00 am-12:10 pm

1 stop6h 10m

Portland

Sun 2/1

1:00 pm-4:35 pm

1 stop3h 35m

$337

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Sat 4/11

6:00 am-11:55 am

1 stop5h 55m

Portland

Mon 4/13

4:50 pm-11:30 pm

1 stop6h 40m

$357

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 4/10

12:30 pm-4:15 pm

1 stop3h 45m

Portland

Sun 4/12

12:40 pm-4:40 pm

1 stop4h 00m

$403

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Mon 12/29

5:50 pm-12:05 am

1 stop6h 15m

Portland

Thu 1/1

5:30 am-12:15 pm

1 stop6h 45m

$443

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Thu 12/25

12:20 pm-9:06 am

1 stop20h 46m

Portland

Mon 12/29

9:46 am-11:25 am

1 stop25h 39m

$731

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Thu 12/25

11:40 am-5:25 pm

3 stops29h 45m

Portland

Mon 12/29

9:46 am-9:58 am

2 stops24h 12m

$1,132

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Sat 4/11

7:00 am-11:47 pm

2 stops16h 47m

Portland

Mon 4/13

6:00 am-10:46 pm

2 stops16h 46m

$1,178

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

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 December.
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 Islip, New York-Portland, Maine flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Islip, New York-Portland, Maine flight deals on Cheapflights vs. eDreams >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 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 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.

Cheapflights Insights

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

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

Currently, April is the cheapest month in which you can book a flight from Islip, New York to Portland, Maine (average of $58). Flying from Islip, New York to Portland, Maine in February is currently the most expensive (average of $165). 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.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated December 12, 2025.
See what other customers who have flown with Southwest from Islip to Portland have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,253 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 $337, Southwest can have you in Portland, Maine from Islip, New York in 6h 10m. There are 243 mi between Islip, New York and Portland, Maine.

  • What is the cheapest airline to fly from Islip, New York to Portland, Maine round-trip?

    Currently priced at $254, Southwest will fly you from Islip, New York to Portland, Maine and back. In addition to Southwest, many other airlines offer competitively priced options for your trip.

  • 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.

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

    Currently, April is the cheapest month in which you can book a flight from Islip, New York to Portland, Maine (average of $58). Flying from Islip, New York to Portland, Maine in February is currently the most expensive (average of $165). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Brunswick
Auburn
Conway

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Top airline flying from Islip to Portland

Discover the top airline that operate flights from Islip to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$254Average$346FlexibilityNo cancel feeOn-time63%

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