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Islip

$226+ Cheap flights from Portland to Islip (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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ISP
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$647
(Southwest)

One-way from

$226
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$367
From Portland to Islip Long Island
Search Deals
One-way flight from Portland to Islip Long Island
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Highest demand for flights based on searches. 7% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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 10/37:35 pmPDX - ISP
2 stops12h 35mSouthwest
Sun 10/511:20 amISP - PDX
2 stops12h 15mSouthwest
Deal found 9/15$647
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/310:30 amPDX - ISP
1 stop21h 25mMultiple Airlines
Sun 10/511:25 amISP - PDX
1 stop12h 25mMultiple Airlines
Deal found 9/16$677
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/229:30 pmPDX - ISP
2 stops10h 28mMultiple Airlines
Thu 9/252:19 pmISP - PDX
1 stop9h 31mMultiple Airlines
Deal found 9/15$854
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/239:30 pmPDX - ISP
2 stops10h 28mMultiple Airlines
Wed 9/242:19 pmISP - PDX
1 stop9h 31mMultiple Airlines
Deal found 9/14$892
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/229:30 pmPDX - ISP
2 stops10h 28mMultiple Airlines
Wed 9/242:19 pmISP - PDX
1 stop9h 31mMultiple Airlines
Deal found 9/15$896
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:30 pmPDX - ISP
2 stops10h 28mMultiple Airlines
Mon 9/294:33 pmISP - PDX
2 stops10h 42mMultiple Airlines
Deal found 9/16$899
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/229:30 pmPDX - ISP
2 stops10h 28mMultiple Airlines
Fri 9/262:19 pmISP - PDX
1 stop9h 31mMultiple Airlines
Deal found 9/16$924
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/198:37 pmPDX - ISP
2 stops11h 21mMultiple Airlines
Sat 9/274:33 pmISP - PDX
2 stops10h 42mMultiple Airlines
Deal found 9/15$927
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/198:37 pmPDX - ISP
2 stops11h 21mMultiple Airlines
Tue 9/302:19 pmISP - PDX
1 stop9h 31mMultiple Airlines
Deal found 9/16$931
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/248:37 pmPDX - ISP
2 stops11h 21mMultiple Airlines
Wed 10/12:19 pmISP - PDX
1 stop9h 31mMultiple Airlines
Deal found 9/16$945

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 September 17, 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

Fri 10/3

7:35 pm-11:10 am

2 stops12h 35m

Islip Long Island

Sun 10/5

11:20 am-8:35 pm

2 stops12h 15m

$647

PortlandIslip

PDX - ISP

PDXISP

Portland

Fri 10/3

10:30 am-10:55 am

1 stop21h 25m

Islip Long Island

Sun 10/5

11:25 am-8:50 pm

1 stop12h 25m

$677

PortlandIslip

PDX - ISP

PDXISP

Portland

Sat 9/27

6:05 am-8:01 pm

2 stops10h 56m

Islip Long Island

Tue 9/30

4:33 pm-12:15 am

2 stops10h 42m

$1,163

PortlandIslip

PDX - ISP

PDXISP

Portland

Tue 10/7

8:50 pm-10:58 am

2 stops11h 08m

Islip Long Island

Wed 10/8

2:19 pm-8:15 pm

1 stop8h 56m

$1,217

PortlandIslip

PDX - ISP

PDXISP

Portland

Thu 10/2

5:58 pm-3:21 pm

2 stops18h 23m

Islip Long Island

Mon 10/6

7:30 am-4:58 pm

2 stops12h 28m

$1,224

PortlandIslip

PDX - ISP

PDXISP

Portland

Fri 10/17

7:35 pm-11:10 am

2 stops12h 35m

$229

PortlandIslip

PDX - ISP

PDXISP

Portland

Sun 12/7

8:39 pm-11:04 am

2 stops11h 25m

$487

PortlandIslip

PDX - ISP

PDXISP

Portland

Thu 12/11

8:39 pm-11:04 am

2 stops11h 25m

$487

PortlandIslip

PDX - ISP

PDXISP

Portland

Fri 11/14

8:45 pm-11:04 am

2 stops11h 19m

$487

PortlandIslip

PDX - ISP

PDXISP

Portland

Mon 12/8

8:39 pm-11:04 am

2 stops11h 25m

$487

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 15 results
1
2

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?

Currently, January is the cheapest month in which you can book a flight from Portland to Islip (average of $108). Flying from Portland to Islip 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 September 17, 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
4,242 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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?

    There are many flights that can get you from Portland to Islip in 12h 35m. Fly via Southwest to get the fastest option. The distance between Portland and Islip is about 2474 mi.

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

    Cheapflights users have booked flights from Portland to Islip round-trip from $361.

  • 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?

    Currently, January is the cheapest month in which you can book a flight from Portland to Islip (average of $108). Flying from Portland to Islip 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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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$361Average$414FlexibilityNo cancel feeOn-time63%

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