ISP - PWM

$280 Find Cheap Flights from Islip to Portland

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Islip to Portland departing on 2/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Portland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Islip to Portland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Islip to Portland, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$280
Southwest
Wed 2/4Wed 2/11
ISP - PWM • 1 stop
Cheapest one-way
Multiple Airlines
Wed 1/14
ISP - PWM • multi-stop
Top airlines
Southwest
Cheapest • from $280 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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We hope you love your trip to Portland!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Islip to Portland (ISP-PWM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Islip to Portland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Islip to Portland

Wed, Feb 4 - Wed, Feb 11
Southwest Logo
3:45 pm - 10:15 pm
ISP
-
PWM
6h 30m
1 stop
Southwest Logo
3:30 pm - 9:55 pm
PWM
-
ISP
6h 25m
1 stop
$280Southwest
Sun, Feb 8 - Wed, Feb 11
Southwest Logo
6:00 am - 12:10 pm
ISP
-
PWM
6h 10m
1 stop
Southwest Logo
3:30 pm - 9:55 pm
PWM
-
ISP
6h 25m
1 stop
$328Southwest
Wed, Jan 28 - Sun, Feb 1
Breeze Airways Logo
7:35 pm - 10:21 am
ISP
-
PWM
14h 46m
1 stop
Breeze Airways Logo
6:19 pm - 1:21 pm
PWM
-
ISP
19h 02m
2 stops
$355Breeze Airways
Sat, Jul 11 - Wed, Jul 15
Southwest Logo
2:45 pm - 9:00 pm
ISP
-
PWM
6h 15m
1 stop
Southwest Logo
5:30 am - 1:45 pm
PWM
-
ISP
8h 15m
1 stop
$363Southwest
Wed, Feb 4 - Wed, Feb 11
Southwest Logo
9:15 am - 10:15 pm
ISP
-
PWM
13h 00m
2 stops
Southwest Logo
3:30 pm - 9:55 pm
PWM
-
ISP
6h 25m
1 stop
$369Southwest
Fri, Feb 6 - Sun, Feb 8
Southwest Logo
4:05 pm - 10:45 pm
ISP
-
PWM
6h 40m
1 stop
Southwest Logo
5:45 am - 11:55 am
PWM
-
ISP
6h 10m
1 stop
$377Southwest
Fri, Feb 6 - Sun, Feb 8
Southwest Logo
12:35 pm - 10:45 pm
ISP
-
PWM
10h 10m
2 stops
Southwest Logo
3:30 pm - 9:55 pm
PWM
-
ISP
6h 25m
1 stop
$382Southwest
Sat, Jul 11 - Wed, Jul 15
Southwest Logo
2:45 pm - 9:00 pm
ISP
-
PWM
6h 15m
1 stop
Southwest Logo
10:30 am - 10:35 pm
PWM
-
ISP
12h 05m
2 stops
$393Southwest
Thu, Apr 9 - Sun, Apr 12
Southwest Logo
4:30 pm - 11:25 pm
ISP
-
PWM
6h 55m
1 stop
Southwest Logo
12:40 pm - 4:40 pm
PWM
-
ISP
4h 00m
1 stop
$407Southwest
Sun, Feb 8 - Wed, Feb 11
Southwest Logo
6:00 am - 12:10 pm
ISP
-
PWM
6h 10m
1 stop
Southwest Logo
5:45 am - 2:35 pm
PWM
-
ISP
8h 50m
2 stops
$459Southwest
Booking Insights

KAYAK's insights & trends for Islip to Portland flights

Get data-powered insights and trends into flights from Islip to Portland to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Islip to Portland?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Islip to Portland were found on Southwest ($280) and Breeze Airways ($355).

Which airlines fly non-stop between Islip and Portland?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Islip to Portland.

There is just one airline that flies from Islip to Portland direct and that is Southwest. The best round-trip deal found from Southwest for the route is $254.

Find deals

Good to know

Cheapest flight$280
Flight from Islip to Portland

When to book flights from Islip to Portland

Are your dates flexible? Find out the best times to travel from Islip to Portland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Islip to Portland

  • What is the cheapest flight from Islip to Portland?

    In the last 3 days, the lowest price for a flight from Islip to Portland was $280 for a round-trip ticket.

  • Do I need a passport to fly between Islip and Portland?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Islip to Portland?

    On your way to Portland, you’ll fly out from Islip Long Island. You’ll be landing at Portland.

  • Which aircraft models fly most regularly from Islip to Portland?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Islip to Portland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Islip to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Islip to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Islip is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Islip to Portland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Portland with an airline and back to Islip with another airline. Booking your flights between Islip and PWM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Islip to Portland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Portland from Islip up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Islip to Portland

 
See real verified KAYAK customer reviews for airlines flying from Islip to Portland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Islip to Portland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4258 reviews
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
8.0Comfort
Airline reviews

3 hour delay. Had to change plans and was still delayed.

2.0 MediocreAnonymous, Jan 2026
SFO - SAN
Read more Southwest reviews

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Everything you need to know for your flight from Islip to Portland

Information on your arrival and departure airports

Islip (ISP)
Portland (PWM)