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$457+ Cheap flights from Islip, NY to Portland (ISP - PDX)

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 3/22. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — PDX
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap flight deals from Islip to Portland

Cheapest flights from Islip to Portland
Explore the most affordable flight options available from Islip to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.

This Southwest deal was found by Cheapflights users on 1/25. 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 3/2211:45 am
ISP
-
PDX
2 stops13h 15m
Southwest
Fri 3/2710:25 am
PDX
-
ISP
2 stops10h 30m
Southwest
Deal found 1/25$457
This Southwest deal was found by Cheapflights users on 1/27. 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 6/1212:30 pm
ISP
-
PDX
2 stops12h 00m
Southwest
Tue 6/169:20 pm
PDX
-
ISP
1 stop7h 45m
Southwest
Deal found 1/27$472
This Southwest deal was found by Cheapflights users on 1/26. 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 2/1012:40 pm
ISP
-
PDX
2 stops12h 25m
Southwest
Sat 2/146:55 am
PDX
-
ISP
2 stops12h 50m
Southwest
Deal found 1/26$577
This Southwest deal was found by Cheapflights users on 1/26. 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.
Mon 2/161:10 pm
ISP
-
PDX
2 stops13h 55m
Southwest
Fri 2/208:50 am
PDX
-
ISP
2 stops11h 40m
Southwest
Deal found 1/26$848
This Expedia deal was found by Cheapflights users on 1/25. 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.
Sun 3/229:59 am
ISP
-
PDX
1 stop12h 49m
Multiple Airlines
Fri 3/277:00 am
PDX
-
ISP
1 stop8h 44m
Multiple Airlines
Deal found 1/25$1,054
This Expedia deal was found by Cheapflights users on 1/27. 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 2/119:59 am
ISP
-
PDX
2 stops17h 10m
Multiple Airlines
Sun 2/157:15 am
PDX
-
ISP
1 stop8h 29m
Multiple Airlines
Deal found 1/27$1,225
This Expedia deal was found by Cheapflights users on 1/26. 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.
Mon 2/169:59 am
ISP
-
PDX
1 stop13h 01m
Multiple Airlines
Fri 2/207:15 am
PDX
-
ISP
1 stop8h 29m
Multiple Airlines
Deal found 1/26$1,304

Find flight deals from Islip to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) to Portland (PDX). 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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$457
(Southwest)

Popular in

December

Cheapest in

February

Average price

$397
Provider with most accurate pricing for Islip Long Island-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Islip Long Island-Portland flights.
Search Deals
From Islip Long Island to Portland
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Islip to Portland 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 January 28, 2026.
Use the filters below to find and compare flights from Islip to Portland that are best for you.

Fly from

Islip

Fly to

Portland

Route

Depart

Return

Price

IslipPortland

ISP - PDX

ISPPDX

Islip Long Island

Sun 3/22

11:45 am-10:00 pm

2 stops13h 15m

Portland

Fri 3/27

10:25 am-11:55 pm

2 stops10h 30m

$457

IslipPortland

ISP - PDX

ISPPDX

Islip Long Island

Fri 6/12

12:30 pm-9:30 pm

2 stops12h 00m

Portland

Tue 6/16

9:20 pm-8:05 am

1 stop7h 45m

$472

IslipPortland

ISP - PDX

ISPPDX

Islip Long Island

Tue 2/10

12:40 pm-10:05 pm

2 stops12h 25m

Portland

Sat 2/14

6:55 am-10:45 pm

2 stops12h 50m

$577

IslipPortland

ISP - PDX

ISPPDX

Islip Long Island

Wed 2/11

12:40 pm-10:35 pm

2 stops12h 55m

Portland

Sun 2/15

6:45 am-10:40 pm

2 stops12h 55m

$577

IslipPortland

ISP - PDX

ISPPDX

Islip Long Island

Mon 2/16

1:10 pm-12:05 am

2 stops13h 55m

Portland

Fri 2/20

8:50 am-11:30 pm

2 stops11h 40m

$848

IslipPortland

ISP - PDX

ISPPDX

Islip Long Island

Sun 3/22

9:59 am-7:48 pm

1 stop12h 49m

Portland

Fri 3/27

7:00 am-6:44 pm

1 stop8h 44m

$1,054

IslipPortland

ISP - PDX

ISPPDX

Islip Long Island

Wed 2/11

9:59 am-12:09 am

2 stops17h 10m

Portland

Sun 2/15

7:15 am-6:44 pm

1 stop8h 29m

$1,225

IslipPortland

ISP - PDX

ISPPDX

Islip Long Island

Mon 2/16

9:59 am-8:00 pm

1 stop13h 01m

Portland

Fri 2/20

7:15 am-6:44 pm

1 stop8h 29m

$1,304

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

  • Most accurate provider: When it comes to deals on Islip, New York-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Islip, New York-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Islip, New York-Portland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Islip, New York-Portland 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 Islip, New York-Portland 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 Islip to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Islip 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 Islip to Portland

What is the cheapest month to book a flight from Islip, New York to Portland?

Currently, February is the cheapest month in which you can book a flight from Islip, New York to Portland (average of $141). Flying from Islip, New York to Portland in November is currently the most expensive (average of $273). 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 Islip to Portland. 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 Islip, New York to Portland?

    A quick flight from Islip, New York to Portland can take about 13h 15m. Southwest provides one of the quickest options available for as low as $457. There are 2474 mi between Islip, New York and Portland.

  • Can I find deals for flights from Islip to Portland that include hotel bookings?

    Yes. In addition to deals on Islip to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Islip to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Islip to Portland.

  • Can I find deals for business class flights from Islip to Portland?

    Yes. Cheapflights offers flight deals from Islip to Portland 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 Islip, New York to Portland?

    Currently, February is the cheapest month in which you can book a flight from Islip, New York to Portland (average of $141). Flying from Islip, New York to Portland in November is currently the most expensive (average of $273). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Seaside
Clackamas
Lincoln City
Longview
Lake Oswego
Beaverton
Hillsboro
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Tillamook
Pacific City
Gresham

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