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$148+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — PWM
May 24 — May 311
Sun 5/24
Sun 5/31
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 April 24, 2026.

This Southwest deal was found by Cheapflights users on 4/23. 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.
Thu 6/45:50 pm
ISP
-
PWM
1 stop6h 15m
Southwest
Mon 6/85:35 am
PWM
-
ISP
1 stop6h 15m
Southwest
Deal found 4/23$288
This Southwest deal was found by Cheapflights users on 4/22. 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.
Sat 6/202:45 pm
ISP
-
PWM
1 stop6h 15m
Southwest
Tue 6/235:30 am
PWM
-
ISP
1 stop8h 15m
Southwest
Deal found 4/22$352
This Southwest deal was found by Cheapflights users on 4/23. 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.
Sat 7/112:45 pm
ISP
-
PWM
1 stop6h 15m
Southwest
Wed 7/155:30 am
PWM
-
ISP
1 stop8h 15m
Southwest
Deal found 4/23$362
This Southwest deal was found by Cheapflights users on 4/23. 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 5/84:30 pm
ISP
-
PWM
1 stop6h 55m
Southwest
Tue 5/126:10 am
PWM
-
ISP
1 stop5h 45m
Southwest
Deal found 4/23$377
This Southwest deal was found by Cheapflights users on 4/24. 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.
Fri 6/55:20 am
ISP
-
PWM
2 stops11h 25m
Southwest
Mon 6/85:35 am
PWM
-
ISP
1 stop6h 15m
Southwest
Deal found 4/24$382
This Southwest deal was found by Cheapflights users on 4/23. 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 8/214:05 pm
ISP
-
PWM
1 stop6h 20m
Southwest
Sun 8/236:10 am
PWM
-
ISP
1 stop3h 45m
Southwest
Deal found 4/23$388
This Southwest deal was found by Cheapflights users on 4/23. 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 8/144:05 pm
ISP
-
PWM
1 stop6h 20m
Southwest
Mon 8/175:55 am
PWM
-
ISP
1 stop6h 40m
Southwest
Deal found 4/23$403
This Southwest deal was found by Cheapflights users on 4/24. 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.
Wed 7/84:40 pm
ISP
-
PWM
1 stop6h 15m
Southwest
Sun 7/125:30 am
PWM
-
ISP
1 stop6h 15m
Southwest
Deal found 4/24$407
This Southwest deal was found by Cheapflights users on 4/22. 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 6/225:50 pm
ISP
-
PWM
1 stop6h 15m
Southwest
Thu 6/253:10 pm
PWM
-
ISP
1 stop8h 25m
Southwest
Deal found 4/22$412
This Southwest deal was found by Cheapflights users on 4/22. 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 6/1512:30 pm
ISP
-
PWM
2 stops9h 40m
Southwest
Tue 6/165:30 am
PWM
-
ISP
1 stop8h 15m
Southwest
Deal found 4/22$418

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 April 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$288
(Southwest)

One-way from

$148
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$238
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. 8% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 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

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Thu 6/4

5:50 pm-12:05 am

1 stop6h 15m

Portland

Mon 6/8

5:35 am-11:50 am

1 stop6h 15m

$288

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Sat 6/20

2:45 pm-9:00 pm

1 stop6h 15m

Portland

Tue 6/23

5:30 am-1:45 pm

1 stop8h 15m

$352
Quickest round-trip

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 6/5

12:30 pm-4:45 pm

1 stop4h 15m

Portland

Mon 6/8

5:20 pm-11:35 pm

1 stop6h 15m

$377

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 5/8

4:30 pm-11:25 pm

1 stop6h 55m

Portland

Tue 5/12

6:10 am-11:55 am

1 stop5h 45m

$377

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 8/21

12:35 pm-9:30 pm

2 stops8h 55m

Portland

Sun 8/23

6:10 am-9:55 am

1 stop3h 45m

$403

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 7/24

5:50 pm-12:05 am

1 stop6h 15m

Portland

Sun 7/26

5:30 am-11:45 am

1 stop6h 15m

$407

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Mon 6/15

12:30 pm-10:10 pm

2 stops9h 40m

Portland

Tue 6/16

5:30 am-1:45 pm

1 stop8h 15m

$418

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 8/14

12:35 pm-9:30 pm

2 stops8h 55m

Portland

Mon 8/17

5:55 am-12:35 pm

1 stop6h 40m

$418
Cheapest one-way

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Thu 7/9

5:50 pm-12:05 am

1 stop6h 15m

$174
Quickest one-way

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Tue 7/21

2:55 pm-6:30 pm

1 stop3h 35m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 16 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 April.
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.

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 April 24, 2026.
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
8.0
Very good
4,334 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,334 reviews
Southwest
8.0
Very good
4,334 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 $288, Southwest can have you in Portland, Maine from Islip, New York in 6h 15m. 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 $336, 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.

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
Lewiston
Conway

Browse thousands of different options on Cheapflights for your next trip

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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 April 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$336Average$472FlexibilityNo cancel feeOn-time63%

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