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Islip

$401+ Cheap flights from Portland to Islip, NY (PDX - ISP)

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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ISP
May 12 — May 191
Tue 5/12
Tue 5/19
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 April 12, 2026.

This Southwest deal was found by Cheapflights users on 4/8. 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 4/2811:55 pm
PDX
-
ISP
2 stops10h 55m
Southwest
Mon 5/44:30 pm
ISP
-
PDX
2 stops10h 40m
Southwest
Deal found 4/8$401
This Southwest deal was found by Cheapflights users on 4/8. 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 5/66:40 am
PDX
-
ISP
2 stops12h 30m
Southwest
Wed 5/139:00 am
ISP
-
PDX
2 stops13h 15m
Southwest
Deal found 4/8$435
This Southwest deal was found by Cheapflights users on 4/11. 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 5/207:25 pm
PDX
-
ISP
2 stops13h 25m
Southwest
Sun 5/2410:20 am
ISP
-
PDX
2 stops15h 35m
Southwest
Deal found 4/11$447
This Southwest deal was found by Cheapflights users on 4/8. 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 9/2310:45 pm
PDX
-
ISP
1 stop7h 55m
Southwest
Sun 9/276:20 am
ISP
-
PDX
1 stop9h 25m
Southwest
Deal found 4/8$467
This Southwest deal was found by Cheapflights users on 4/10. 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.
Fri 7/177:40 pm
PDX
-
ISP
2 stops12h 55m
Southwest
Mon 7/2012:30 pm
ISP
-
PDX
2 stops12h 00m
Southwest
Deal found 4/10$483
This Southwest deal was found by Cheapflights users on 4/11. 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 5/295:10 am
PDX
-
ISP
2 stops8h 20m
Southwest
Sun 5/3111:50 am
ISP
-
PDX
2 stops14h 00m
Southwest
Deal found 4/11$537
This Southwest deal was found by Cheapflights users on 4/8. 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 4/236:10 am
PDX
-
ISP
2 stops13h 20m
Southwest
Mon 4/274:30 pm
ISP
-
PDX
2 stops11h 25m
Southwest
Deal found 4/8$597
This Expedia deal was found by Cheapflights users on 4/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:30 pm
PDX
-
ISP
2 stops16h 40m
Multiple Airlines
Fri 5/159:59 am
ISP
-
PDX
1 stop13h 48m
Multiple Airlines
Deal found 4/9$980

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 April 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$401
(Southwest)

Popular in

December

Cheapest in

February

Average price

$364
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
Highest demand for flights based on searches. 9% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 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 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 April 12, 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

Cheapest round-trip

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 4/29

5:40 am-6:30 pm

2 stops9h 50m

Islip Long Island

Thu 5/7

4:30 pm-12:55 am

2 stops11h 25m

$401

PortlandIslip

PDX - ISP

PDXISP

Portland

Tue 4/28

11:55 pm-1:50 pm

2 stops10h 55m

Islip Long Island

Mon 5/4

4:30 pm-12:10 am

2 stops10h 40m

$401

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 5/20

7:25 pm-11:50 am

2 stops13h 25m

Islip Long Island

Sun 5/24

10:20 am-10:55 pm

2 stops15h 35m

$447

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 9/23

10:45 pm-9:40 am

1 stop7h 55m

Islip Long Island

Sun 9/27

6:20 am-12:45 pm

1 stop9h 25m

$467
Quickest round-trip

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 9/23

10:45 pm-9:40 am

1 stop7h 55m

Islip Long Island

Mon 9/28

10:20 am-3:00 pm

1 stop7h 40m

$467

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/8

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 April.
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, March is the cheapest month in which you can book a flight from Portland to Islip, New York (average of $143). 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.

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 April 12, 2026.
Read through reviews of airlines operating flights from Portland to Islip, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,331 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

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
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

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 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 9h 50m. 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, March is the cheapest month in which you can book a flight from Portland to Islip, New York (average of $143). 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?

Book flights to Islip if you plan to visit one of these locations
Riverhead

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Top airline flying from Portland to Islip

Discover the top airline that operate flights from Portland to Islip. 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 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$361Average$437FlexibilityNo cancel feeOn-time63%

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