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Islip

$224+ Cheap flights from Portland to Islip, NY (PDX - 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ISP
Mar 29 — Apr 51
Sun 3/29
Sun 4/5
1 adult, Economy
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Cheap 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 February 27, 2026.

This Southwest deal was found by Cheapflights users on 2/24. 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.
Tue 6/28:50 am
PDX
-
ISP
2 stops10h 20m
Southwest
Tue 6/99:00 am
ISP
-
PDX
1 stop9h 25m
Southwest
Deal found 2/24$452
This Southwest deal was found by Cheapflights users on 2/25. 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.
Fri 5/18:35 am
PDX
-
ISP
2 stops11h 55m
Southwest
Sun 5/105:25 pm
ISP
-
PDX
2 stops9h 40m
Southwest
Deal found 2/25$457
This Southwest deal was found by Cheapflights users on 2/25. 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.
Sun 6/711:30 pm
PDX
-
ISP
2 stops12h 00m
Southwest
Sat 6/133:30 pm
ISP
-
PDX
2 stops11h 25m
Southwest
Deal found 2/25$467
This Southwest deal was found by Cheapflights users on 2/23. 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.
Wed 3/116:30 am
PDX
-
ISP
2 stops13h 20m
Southwest
Sun 3/1511:45 am
ISP
-
PDX
2 stops13h 15m
Southwest
Deal found 2/23$577
This Travelocity deal was found by Cheapflights users on 2/24. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:37 am
PDX
-
ISP
1 stop8h 08m
Multiple Airlines
Tue 6/912:30 pm
ISP
-
PDX
1 stop11h 17m
Multiple Airlines
Deal found 2/24$1,024
This Expedia deal was found by Cheapflights users on 2/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:15 am
PDX
-
ISP
1 stop8h 29m
Multiple Airlines
Sun 3/159:59 am
ISP
-
PDX
1 stop13h 01m
Multiple Airlines
Deal found 2/23$1,244
This Expedia deal was found by Cheapflights users on 2/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:30 pm
PDX
-
ISP
2 stops11h 35m
Multiple Airlines
Sun 5/109:59 am
ISP
-
PDX
1 stop13h 26m
Multiple Airlines
Deal found 2/25$1,260

Find flight deals from Portland to Islip

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) 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 February 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$452
(Southwest)

One-way from

$224
(Southwest)

Popular in

December

Cheapest in

February

Average price

$337
Provider with most accurate pricing for Portland-Islip Long Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Islip Long Island flights.
Search Deals
From Portland to Islip Long Island
Search Deals
One-way flight from Portland to Islip Long Island
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 27, 2026.
Use the filters below to find and compare flights from Portland to Islip that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandIslip

PDX - ISP

PDXISP

Portland

Sun 6/7

9:20 pm-8:20 am

1 stop8h 00m

Islip Long Island

Sat 6/13

3:30 pm-11:55 pm

2 stops11h 25m

$452

PortlandIslip

PDX - ISP

PDXISP

Portland

Tue 6/2

6:30 am-10:10 pm

2 stops12h 40m

Islip Long Island

Tue 6/9

4:40 pm-11:50 pm

2 stops10h 10m

$457

PortlandIslip

PDX - ISP

PDXISP

Portland

Fri 5/1

8:35 am-11:30 pm

2 stops11h 55m

Islip Long Island

Sun 5/10

5:25 pm-12:05 am

2 stops9h 40m

$457

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 3/11

6:30 am-10:50 pm

2 stops13h 20m

Islip Long Island

Sun 3/15

11:45 am-10:00 pm

2 stops13h 15m

$577

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 3/11

7:15 am-6:44 pm

1 stop8h 29m

Islip Long Island

Sun 3/15

9:59 am-8:00 pm

1 stop13h 01m

$1,244

PortlandIslip

PDX - ISP

PDXISP

Portland

Fri 5/1

8:30 pm-11:05 am

2 stops11h 35m

Islip Long Island

Sun 5/10

9:59 am-8:25 pm

1 stop13h 26m

$1,260

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 6/17

9:20 pm-8:20 am

1 stop8h 00m

$224

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 6/17

12:23 pm-6:06 pm

3 stops26h 43m

$391

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/23

Sorted by cheapest first

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 February.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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-Islip, New York flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Islip, New York flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Islip, New York flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-Islip, New York 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 Portland-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 to Islip, New York?

Currently, May is the cheapest month in which you can book a flight from Portland to Islip, New York (average of $158). Flying from Portland to Islip, New York in October is currently the most expensive (average of $257). 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 to Islip, New York?

    Departing from Portland to Islip, New York will take you 10h 20m. Airlines will cover a distance of 2474 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 to Islip, New York?

    Currently, May is the cheapest month in which you can book a flight from Portland to Islip, New York (average of $158). Flying from Portland to Islip, New York in October is currently the most expensive (average of $257). 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?

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