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$163+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ISP
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$985
(Expedia)

One-way from

$163
(Cheapflightsfares)

Popular in

December

Cheapest in

January

Average price

$397
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. 7% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This Expedia deal was found by Cheapflights users on 8/12. 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.
Tue 8/196:51 amPDX - ISP
2 stops14h 08mFrontier
Tue 8/266:05 amISP - PDX
2 stops19h 34mFrontier
Deal found 8/12$396
This Southwest deal was found by Cheapflights users on 8/12. 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 8/199:05 pmPDX - ISP
1 stop11h 50mSouthwest
Tue 8/266:05 amISP - PDX
1 stop10h 45mSouthwest
Deal found 8/12$692
This Expedia deal was found by Cheapflights users on 8/13. 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.
Tue 8/199:37 pmPDX - ISP
1 stop10h 21mMultiple Airlines
Tue 8/266:05 amISP - PDX
2 stops19h 34mMultiple Airlines
Deal found 8/13$930
This Expedia deal was found by Cheapflights users on 8/12. 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 8/276:51 amPDX - ISP
2 stops13h 50mMultiple Airlines
Sun 8/312:19 pmISP - PDX
1 stop9h 31mMultiple Airlines
Deal found 8/12$985

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 August 14, 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 8/27

6:51 am-11:41 pm

2 stops13h 50m

Islip Long Island

Sun 8/31

2:19 pm-8:50 pm

1 stop9h 31m

$985

PortlandIslip

PDX - ISP

PDXISP

Portland

Mon 11/3

8:45 pm-10:58 am

2 stops11h 13m

Islip Long Island

Fri 11/7

2:19 pm-8:07 pm

1 stop8h 48m

$999

PortlandIslip

PDX - ISP

PDXISP

Portland

Wed 12/31

6:14 am-8:01 pm

2 stops10h 47m

Islip Long Island

Wed 1/7

2:19 pm-8:15 pm

1 stop8h 56m

$1,059

PortlandIslip

PDX - ISP

PDXISP

Portland

Sun 9/28

9:30 pm-10:58 am

2 stops10h 28m

Islip Long Island

Fri 10/3

4:33 pm-12:15 am

2 stops10h 42m

$1,074

PortlandIslip

PDX - ISP

PDXISP

Portland

Sun 10/12

8:50 pm-10:58 am

2 stops11h 08m

Islip Long Island

Fri 10/17

2:19 pm-8:15 pm

1 stop8h 56m

$1,099

PortlandIslip

PDX - ISP

PDXISP

Portland

Mon 9/8

9:30 pm-10:58 am

2 stops10h 28m

Islip Long Island

Wed 9/10

4:33 pm-12:15 am

2 stops10h 42m

$1,104

PortlandIslip

PDX - ISP

PDXISP

Portland

Sun 9/21

8:37 pm-10:58 am

2 stops11h 21m

Islip Long Island

Tue 9/23

4:33 pm-12:15 am

2 stops10h 42m

$1,104

PortlandIslip

PDX - ISP

PDXISP

Portland

Tue 9/30

9:30 pm-10:58 am

2 stops10h 28m

Islip Long Island

Fri 10/3

4:33 pm-12:15 am

2 stops10h 42m

$1,124

PortlandIslip

PDX - ISP

PDXISP

Portland

Sun 11/23

8:38 pm-10:58 am

2 stops11h 20m

Islip Long Island

Tue 11/25

2:19 pm-8:49 pm

1 stop9h 30m

$1,149

PortlandIslip

PDX - ISP

PDXISP

Portland

Mon 9/15

8:37 pm-10:58 am

2 stops11h 21m

Islip Long Island

Thu 9/18

4:33 pm-12:15 am

2 stops10h 42m

$1,154

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 19 results
1
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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, January is the cheapest month in which you can book a flight from Portland to Islip, New York (average of $108). Flying from Portland 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 August 14, 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
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • 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, January is the cheapest month in which you can book a flight from Portland to Islip, New York (average of $108). Flying from Portland 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
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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$361Average$437FlexibilityNo cancel feeOn-time63%

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