HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$133+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — PWM
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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.

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 October 28, 2025.

This Southwest deal was found by Cheapflights users on 10/25. 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.
Mon 12/225:50 pmISP - PWM
1 stop6h 15mSouthwest
Mon 12/295:30 pmPWM - ISP
1 stop6h 25mSouthwest
Deal found 10/25$367
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/67:36 pmISP - PWM
2 stops21h 49mMultiple Airlines
Mon 11/109:46 amPWM - ISP
1 stop9h 20mMultiple Airlines
Deal found 10/27$383
This Southwest deal was found by Cheapflights users on 10/27. 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.
Wed 11/125:40 amISP - PWM
1 stop6h 30mSouthwest
Sat 11/153:15 pmPWM - ISP
1 stop6h 30mSouthwest
Deal found 10/27$419
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/277:08 pmISP - PWM
1 stop22h 41mMultiple Airlines
Mon 11/36:05 pmPWM - ISP
2 stops40h 32mMultiple Airlines
Deal found 10/26$431
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/298:45 pmISP - PWM
1 stop20h 15mMultiple Airlines
Fri 10/319:46 amPWM - ISP
1 stop24h 51mMultiple Airlines
Deal found 10/25$493
This Southwest deal was found by Cheapflights users on 10/27. 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 11/711:05 amISP - PWM
1 stop5h 45mSouthwest
Sun 11/95:25 pmPWM - ISP
1 stop6h 25mSouthwest
Deal found 10/27$537
This Southwest deal was found by Cheapflights users on 10/27. 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.
Thu 11/63:25 pmISP - PWM
2 stops8h 55mSouthwest
Mon 11/1011:50 amPWM - ISP
2 stops10h 45mSouthwest
Deal found 10/27$557

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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$367
(Southwest)

One-way from

$133
(Southwest)

Popular in

November

Cheapest in

May

Average price

$237
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
One-way flight from Islip Long Island to Portland
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($89 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 28, 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

Mon 12/22

5:50 pm-12:05 am

1 stop6h 15m

Portland

Mon 12/29

5:30 pm-11:55 pm

1 stop6h 25m

$367

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Thu 11/6

7:36 pm-5:25 pm

2 stops21h 49m

Portland

Mon 11/10

9:46 am-7:06 pm

1 stop9h 20m

$383

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Wed 11/12

5:40 am-12:10 pm

1 stop6h 30m

Portland

Sat 11/15

3:15 pm-9:45 pm

1 stop6h 30m

$419

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 11/7

11:05 am-4:50 pm

1 stop5h 45m

Portland

Sun 11/9

5:25 pm-11:50 pm

1 stop6h 25m

$537

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Thu 11/6

3:25 pm-12:20 am

2 stops8h 55m

Portland

Mon 11/10

11:50 am-10:35 pm

2 stops10h 45m

$557

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Wed 11/12

8:45 pm-2:30 pm

3 stops17h 45m

Portland

Sat 11/15

6:18 pm-11:00 am

2 stops16h 42m

$634

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Sat 11/1

6:05 am-9:55 am

1 stop3h 50m

Portland

Sat 11/8

3:15 pm-9:45 pm

1 stop6h 30m

$637

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Wed 12/3

3:55 pm-10:15 pm

1 stop6h 20m

$133

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Sun 11/16

9:27 pm-9:06 am

1 stop11h 39m

$141

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Sun 11/16

11:40 am-9:06 am

2 stops21h 26m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 11 results
1
2

Compare providers for flights from Islip to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Islip to Portland in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

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

Currently, April is the cheapest month in which you can book a flight from Islip, New York to Portland, Maine (average of $58). Flying from Islip, New York to Portland, Maine in February is currently the most expensive (average of $124). 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 October 28, 2025.
See what other customers who have flown with Southwest 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
4,240 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

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 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, Maine?

    For as low as $367, Southwest can have you in Portland, Maine from Islip, New York in 6h 15m. There are 243 mi between Islip, New York and Portland, Maine.

  • What is the cheapest airline to fly from Islip, New York to Portland, Maine round-trip?

    Currently priced at $254, 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. Southwest is currently priced 35% 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, April is the cheapest month in which you can book a flight from Islip, New York to Portland, Maine (average of $58). Flying from Islip, New York to Portland, Maine in February is currently the most expensive (average of $124). 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
North Conway
Brunswick
Auburn
Conway

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.
LaGuardia to Boston flights
John F Kennedy Intl to Boston flights
Newark to Boston flights
Islip to Boston flights
LaGuardia to Portland flights
Buffalo to Boston flights
Newark to Portland flights
John F Kennedy Intl to Portland flights
Rochester to Boston flights
Stewart to Boston flights
Syracuse to Boston flights
LaGuardia to Bangor flights
John F Kennedy Intl to Bangor flights
Saranac Lake to Boston flights
Newark to Bangor flights
White Plains to Portland flights
White Plains to Boston flights
Rochester to Portland flights
Albany to Boston flights
Buffalo to Portland flights
Ithaca to Boston flights
Syracuse to Portland flights
Albany to Portland flights
John F Kennedy Intl to Bar Harbor flights
Syracuse to Bangor flights
Stewart to Portland flights
John F Kennedy Intl to Augusta flights
Buffalo to Bangor flights
Albany to Bangor flights
White Plains to Bangor flights
Rutland to Boston flights
Rochester to Bangor flights
Elmira to Boston flights
Newark to Bar Harbor flights
Buffalo to Rockland flights
Stewart to Bangor flights
Newark to Augusta flights
Binghamton to Portland flights
White Plains to Augusta flights
White Plains to Bar Harbor flights
Niagara Falls to Boston flights
Watertown to Boston flights
John F Kennedy Intl to Rockland flights
Ithaca to Bangor flights
Ithaca to Portland flights
Binghamton to Boston flights
LaGuardia to Augusta flights
Islip to Bangor flights
LaGuardia to Bar Harbor 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 October 28, 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.