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$164+ Cheap flights from Islip 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 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — PWM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$216
(Southwest)

One-way from

$164
(Southwest)

Popular in

October

Cheapest in

August

Average price

$367
From Islip Long Island to Portland
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One-way flight from Islip Long Island to Portland
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Highest demand for flights based on searches. 31% potential increase in price ($185 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($32 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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 11/83:40 pmISP - PWM
1 stop6h 15mSouthwest
Sat 11/153:15 pmPWM - ISP
1 stop6h 30mSouthwest
Deal found 9/10$216
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Fri 9/267:08 pmISP - PWM
2 stops18h 33mBreeze Airways
Tue 9/301:18 pmPWM - ISP
1 stop30h 47mBreeze Airways
Deal found 9/11$319
This Southwest deal was found by Cheapflights users on 9/10. 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 11/215:50 amISP - PWM
1 stop5h 20mSouthwest
Sun 11/235:25 pmPWM - ISP
1 stop6h 25mSouthwest
Deal found 9/10$327
This Southwest deal was found by Cheapflights users on 9/11. 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 10/74:55 pmISP - PWM
1 stop5h 35mSouthwest
Wed 10/87:40 amPWM - ISP
1 stop4h 45mSouthwest
Deal found 9/11$367
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/169:37 pmISP - PWM
1 stop11h 29mMultiple Airlines
Sun 10/195:40 pmPWM - ISP
1 stop24h 48mMultiple Airlines
Deal found 9/11$398
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/247:32 pmISP - PWM
1 stop21h 28mBreeze Airways
Tue 9/301:18 pmPWM - ISP
1 stop30h 47mBreeze Airways
Deal found 9/11$408
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/157:08 pmISP - PWM
1 stop17h 10mBreeze Airways
Wed 9/174:41 pmPWM - ISP
1 stop26h 15mBreeze Airways
Deal found 9/11$421
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Fri 9/265:05 pmISP - PWM
1 stop21h 21mMultiple Airlines
Tue 9/301:18 pmPWM - ISP
1 stop30h 47mMultiple Airlines
Deal found 9/11$437

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 September 11, 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 11/8

3:40 pm-9:55 pm

1 stop6h 15m

Portland

Sat 11/15

3:15 pm-9:45 pm

1 stop6h 30m

$216

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 9/26

7:08 pm-1:41 pm

2 stops18h 33m

Portland

Tue 9/30

1:18 pm-8:05 pm

1 stop30h 47m

$319

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 11/21

5:50 am-11:10 am

1 stop5h 20m

Portland

Sun 11/23

5:25 pm-11:50 pm

1 stop6h 25m

$327

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Tue 10/7

4:55 pm-10:30 pm

1 stop5h 35m

Portland

Wed 10/8

7:40 am-12:25 pm

1 stop4h 45m

$367

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Wed 9/24

7:32 pm-5:00 pm

1 stop21h 28m

Portland

Tue 9/30

1:18 pm-8:05 pm

1 stop30h 47m

$408

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 9/26

5:05 pm-2:26 pm

1 stop21h 21m

Portland

Tue 9/30

1:18 pm-8:05 pm

1 stop30h 47m

$437

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Wed 10/8

6:00 am-11:15 am

1 stop5h 15m

Portland

Thu 10/9

11:45 am-4:50 pm

1 stop5h 05m

$492

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Wed 11/26

5:50 pm-12:05 am

1 stop6h 15m

$164

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Wed 10/8

6:00 am-11:15 am

1 stop5h 15m

$210

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Wed 10/8

8:45 pm-2:30 pm

3 stops17h 45m

$355

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 11 results
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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 to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Islip to Portland, Maine (average of $296). Flying from Islip 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.

How much does it cost to fly round-trip from Islip to Portland, Maine?

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 September 11, 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
4,248 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

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 to Portland, Maine?

    For as low as $216, Southwest can have you in Portland, Maine from Islip in 6h 15m. Airlines will cover a distance of 243 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Currently priced at $280, Southwest will fly you from Islip to Portland, Maine and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Southwest is priced at 30% lower than the current average price of a flight leaving 3 months from now.

  • 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 to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Islip to Portland, Maine (average of $296). Flying from Islip 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

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Alternative routes for Islip to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$280Average$396FlexibilityNo cancel feeOn-time63%

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