HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$179+ Cheap flights from Islip, NY to Portland, ME (ISP - PWM)

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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — PWM
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Islip to Portland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 (PWM). 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 July 29, 2025.

Round-trip from

$252
(Southwest)

One-way from

$179
(Southwest)

Popular in

October

Cheapest in

August

Average price

$247
From Islip Long Island to Portland
Search Deals
One-way flight from Islip Long Island to Portland
Search Deals
Highest demand for flights based on searches. 34% potential increase in price ($197 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find 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 July 29, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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.
Sat 8/303:40 pmISP - PWM
1 stop6h 20mSouthwest
Sun 8/316:10 amPWM - ISP
1 stop6h 40mSouthwest
Deal found 7/28$252
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/191:55 pmISP - PWM
2 stops29h 32mBreeze Airways
Tue 8/261:50 pmPWM - ISP
2 stops28h 55mBreeze Airways
Deal found 7/29$566

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 July 29, 2025.
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 - PWM

ISPPWM

Islip Long Island

Sat 8/30

3:40 pm-10:00 pm

1 stop6h 20m

Portland

Sun 8/31

6:10 am-12:50 pm

1 stop6h 40m

$252

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Tue 8/19

1:55 pm-7:27 pm

2 stops29h 32m

Portland

Tue 8/26

1:50 pm-6:45 pm

2 stops28h 55m

$566

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Tue 8/19

5:30 am-4:20 pm

2 stops10h 50m

$179

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Tue 8/12

1:55 pm-7:27 pm

2 stops29h 32m

$296

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 8/1

10:36 am-11:35 am

3 stops24h 59m

$734

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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, Maine?

Currently, January is the cheapest month in which you can book a flight from Islip, New York to Portland, Maine (average of $296). Flying from Islip, New York to Portland, Maine in July is currently the most expensive (average of $394). 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 Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated July 29, 2025.
See what other customers who have flown with Southwest and Breeze Airways from Islip to Portland have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Breeze Airways
8.0
Very good
190 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • What are the cheapest airlines flying from Islip, New York to Portland, Maine round-trip?

    Currently priced at $252, Southwest will fly you from Islip, New York to Portland, Maine and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Breeze Airways for as low as $566. Southwest is currently priced 31% below the average price you’ll pay for this route.

  • 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, Maine?

    Currently, January is the cheapest month in which you can book a flight from Islip, New York to Portland, Maine (average of $296). Flying from Islip, New York to Portland, Maine in July is currently the most expensive (average of $394). 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
Brunswick
North Conway
Auburn
Conway
Lewiston

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Islip to Portland

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Boston flights
LaGuardia to Boston flights
John F Kennedy Intl to Boston flights
John F Kennedy Intl to Portland flights
Newark to Portland flights
LaGuardia to Portland flights
Newark to Bangor flights
Islip to Boston flights
John F Kennedy Intl to Bangor flights
Buffalo to Boston flights
Stewart to Portland flights
LaGuardia to Bangor flights
Rochester to Boston flights
White Plains to Boston flights
Syracuse to Boston flights
John F Kennedy Intl to Bar Harbor flights
Stewart to Boston flights
Rochester to Portland flights
Buffalo to Portland flights
Newark to Bar Harbor flights
John F Kennedy Intl to Augusta flights
Syracuse to Portland flights
Buffalo to Bangor flights
Albany to Boston flights
White Plains to Portland flights
LaGuardia to Bar Harbor flights
White Plains to Augusta flights
Albany to Portland flights
Syracuse to Bangor flights
John F Kennedy Intl to Rockland flights
Newark to Augusta flights
Rochester to Bangor flights
White Plains to Bangor flights
Albany to Bangor flights
Ithaca to Boston flights
Binghamton to Boston flights
LaGuardia to Augusta flights
White Plains to Bar Harbor flights
Saranac Lake to Boston flights
Rutland to Boston flights
Newark to Rockland flights
Ithaca to Portland flights
Stewart to Bangor flights
Islip to Bangor flights
Elmira to Boston flights
LaGuardia to Rockland flights
Watertown to Bangor flights
Plattsburgh to Boston flights
Watertown to Boston flights

Top airline flying from Islip to Portland

Discover the top airline that operate flights from Islip to Portland. 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$254Average$346FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.