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Islip

$154+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ISP
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$317
(Southwest)

One-way from

$154
(Southwest)

Popular in

February

Cheapest in

September

Average price

$217
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 ($45 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 July 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 July 29, 2025.

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.
Sat 9/138:15 amPWM - ISP
1 stop3h 50mSouthwest
Sat 9/203:40 pmISP - PWM
1 stop6h 20mSouthwest
Deal found 7/27$317
This KAYAK deal was found by Cheapflights users on 7/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/185:33 pmPWM - ISP
1 stop24h 55mBreeze Airways
Sun 9/217:36 pmISP - PWM
2 stops21h 49mBreeze Airways
Deal found 7/29$573
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/121:50 pmPWM - ISP
2 stops23h 42mMultiple Airlines
Sat 8/167:30 amISP - PWM
3 stops28h 21mMultiple Airlines
Deal found 7/28$1,187

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 29, 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

Sat 9/13

8:15 am-12:05 pm

1 stop3h 50m

Islip Long Island

Sat 9/20

3:40 pm-10:00 pm

1 stop6h 20m

$317

PortlandIslip

PWM - ISP

PWMISP

Portland

Thu 9/18

5:33 pm-6:28 pm

1 stop24h 55m

Islip Long Island

Sun 9/21

7:36 pm-5:25 pm

2 stops21h 49m

$573

PortlandIslip

PWM - ISP

PWMISP

Portland

Tue 8/12

1:50 pm-1:32 pm

2 stops23h 42m

Islip Long Island

Sat 8/16

7:30 am-11:51 am

3 stops28h 21m

$1,187

PortlandIslip

PWM - ISP

PWMISP

Portland

Tue 8/26

9:05 am-3:10 pm

1 stop6h 05m

$154

PortlandIslip

PWM - ISP

PWMISP

Portland

Sat 9/27

4:41 pm-6:56 pm

1 stop26h 15m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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, January is the cheapest month in which you can book a flight from Portland, Maine to Islip, New York (average of $108). Flying from Portland, Maine to Islip, New York 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.

Reviews of airlines servicing Islip

Get insights into the airlines that provide service to Islip. 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 Islip. Reviews last updated July 29, 2025.
Read reviews from past customers who have flown Southwest and Breeze Airways from Portland to Islip. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Breeze Airways
8.0
Very good
190 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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, January is the cheapest month in which you can book a flight from Portland, Maine to Islip, New York (average of $108). Flying from Portland, Maine to Islip, New York 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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