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Islip

$413+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ISP
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 (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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$413
(Southwest)

Popular in

December

Cheapest in

January

Average price

$377
Provider with most accurate pricing for Portland-Islip Long Island flight deals.
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Provider most trusted by Cheapflights users for Portland-Islip Long Island flights.
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From Portland to Islip Long Island
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This Southwest deal was found by Cheapflights users on 10/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/108:00 amPDX - ISP
2 stops11h 05mSouthwest
Sun 12/145:50 amISP - PDX
2 stops12h 15mSouthwest
Deal found 10/29$413
This Southwest deal was found by Cheapflights users on 10/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:00 amPDX - ISP
2 stops11h 05mSouthwest
Thu 1/112:55 pmISP - PDX
2 stops12h 40mSouthwest
Deal found 10/29$423
This Expedia deal was found by Cheapflights users on 10/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:04 amPDX - ISP
1 stop9h 41mMultiple Airlines
Sun 12/1412:40 pmISP - PDX
2 stops14h 14mMultiple Airlines
Deal found 10/29$959
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Wed 12/249:42 pmPDX - ISP
1 stop15h 33mMultiple Airlines
Wed 12/3112:40 pmISP - PDX
1 stop23h 48mMultiple Airlines
Deal found 10/30$1,030
This Expedia deal was found by Cheapflights users on 10/30. 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 12/249:42 pmPDX - ISP
1 stop10h 22mMultiple Airlines
Thu 1/19:59 amISP - PDX
1 stop13h 37mMultiple Airlines
Deal found 10/30$1,069
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:30 pmPDX - ISP
2 stops18h 45mMultiple Airlines
Mon 11/177:30 amISP - PDX
2 stops13h 00mMultiple Airlines
Deal found 10/29$1,170

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 October 30, 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

PDX - ISP

PDXISP

Portland

Wed 12/10

8:00 am-10:05 pm

2 stops11h 05m

Islip Long Island

Sun 12/14

5:50 am-3:05 pm

2 stops12h 15m

$413

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 12/24

8:00 am-10:05 pm

2 stops11h 05m

Islip Long Island

Thu 1/1

12:55 pm-10:35 pm

2 stops12h 40m

$423

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 12/24

8:00 am-10:05 pm

2 stops11h 05m

Islip Long Island

Wed 12/31

12:55 pm-10:00 pm

2 stops12h 05m

$423

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 12/10

7:04 am-7:45 pm

1 stop9h 41m

Islip Long Island

Sun 12/14

12:40 pm-11:54 pm

2 stops14h 14m

$959

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 12/24

9:42 pm-4:15 pm

1 stop15h 33m

Islip Long Island

Wed 12/31

12:40 pm-9:28 am

1 stop23h 48m

$1,030

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 12/24

9:42 pm-11:04 am

1 stop10h 22m

Islip Long Island

Thu 1/1

9:59 am-8:36 pm

1 stop13h 37m

$1,069

PortlandIslip

PDX - ISP

PDXISP

Portland

Thu 11/13

6:30 pm-4:15 pm

2 stops18h 45m

Islip Long Island

Mon 11/17

7:30 am-5:30 pm

2 stops13h 00m

$1,170

PortlandIslip

PDX - ISP

PDXISP

Portland

Tue 1/6

8:32 pm-11:04 am

2 stops11h 32m

$468

PortlandIslip

PDX - ISP

PDXISP

Portland

Fri 12/12

8:44 pm-11:04 am

2 stops11h 20m

$507

PortlandIslip

PDX - ISP

PDXISP

Portland

Mon 1/5

8:32 pm-11:04 am

2 stops11h 32m

$507

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 17 results
1
2

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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
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 Portland-Islip, New York flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland-Islip, New York flight deals on Cheapflights vs. eDreams >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 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 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, February is the cheapest month in which you can book a flight from Portland to Islip, New York (average of $104). Flying from Portland to Islip, New York in October is currently the most expensive (average of $254). 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 October 30, 2025.
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
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 11h 05m. Airlines will cover a distance of 2474 mi.

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

    Currently priced at $361, Southwest will fly you from Portland to Islip, New York and back. In addition to Southwest, many other airlines offer competitively priced options for your trip.

  • 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, February is the cheapest month in which you can book a flight from Portland to Islip, New York (average of $104). Flying from Portland to Islip, New York in October is currently the most expensive (average of $254). 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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Alternative routes for Portland to Islip

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$361Average$437FlexibilityNo cancel feeOn-time63%

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