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$154+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — PWM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$298
(Southwest)

One-way from

$154
(Southwest)

Popular in

October

Cheapest in

July

Average price

$411
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. 38% potential increase in price ($217 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($37 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/10. 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.
Tue 7/84:40 pmISP - PWM
1 stop6h 45mSouthwest
Tue 7/155:30 amPWM - ISP
1 stop6h 30mSouthwest
Deal found 6/10$298
This KAYAK deal was found by Cheapflights users on 6/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/262:25 pmISP - PWM
1 stop23h 16mBreeze Airways
Sun 9/285:33 pmPWM - ISP
1 stop24h 55mBreeze Airways
Deal found 6/10$562
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/203:59 pmISP - PWM
3 stops19h 54mMultiple Airlines
Sun 6/2212:46 pmPWM - ISP
3 stops21h 10mMultiple Airlines
Deal found 6/10$1,183

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 June 12, 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

Tue 7/8

4:40 pm-11:25 pm

1 stop6h 45m

Portland

Tue 7/15

5:30 am-12:00 pm

1 stop6h 30m

$298

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 9/26

2:25 pm-1:41 pm

1 stop23h 16m

Portland

Sun 9/28

5:33 pm-6:28 pm

1 stop24h 55m

$562

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Mon 7/28

6:00 am-10:45 am

1 stop4h 45m

$154

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Fri 7/11

10:44 am-9:43 am

2 stops22h 59m

$385

IslipPortland

ISP - PWM

ISPPWM

Islip Long Island

Thu 7/3

7:39 pm-11:57 am

3 stops40h 18m

$520

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Read reviews from past customers who have flown Breeze Airways and Southwest from Islip to Portland. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Entertainment

6.6

Overall

8.1

Boarding

8.3

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
178 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Entertainment

6.6

Overall

8.1

Boarding

8.3

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,287 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Entertainment

6.6

Overall

8.1

Boarding

8.3

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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 $298, 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 $562. Southwest is currently priced 15% 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 Islip?

Book flights to Islip if you plan to visit one of these locations
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

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Alternative routes for Islip to Portland

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Top 2 airlines flying from Islip to Portland

Discover the top 2 airlines 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$95Average$125FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$254Average$336FlexibilityNo cancel feeOn-time63%

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