$463 Cheap Flights from Portland (PWM) to Naples (NAP)

View $463 flight on Wed, Oct 15, 2025Opens in a new window

Popular airlines from Portland Intl. Jetport Airport (PWM) to Naples Intl. Airport (NAP)

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Cheap Flights from Portland to Naples (PWM-NAP)

Prices were available within the past 7 days and start at $463 for one-way flights and $593 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Oct 22 - Wed, Nov 12
PWM
Portland
NAP
Naples
$593 Roundtrip, found 2 days ago
$593
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Oct 22 from Portland to Naples, returning Wed, Nov 12, priced at $593 found 2 days ago
United
Tue, Oct 14 - Mon, Nov 3
PWM
Portland
NAP
Naples
$604 Roundtrip, found 1 day ago
$604
Roundtrip
found 1 day ago
Select United flight, departing Tue, Oct 14 from Portland to Naples, returning Mon, Nov 3, priced at $604 found 1 day ago
United
Wed, Oct 22 - Tue, Nov 11
PWM
Portland
NAP
Naples
$604 Roundtrip, found 2 days ago
$604
Roundtrip
found 2 days ago
Select United flight, departing Wed, Oct 22 from Portland to Naples, returning Tue, Nov 11, priced at $604 found 2 days ago
United
Mon, Oct 13 - Mon, Nov 3
PWM
Portland
NAP
Naples
$609 Roundtrip, found 1 day ago
$609
Roundtrip
found 1 day ago
Select United flight, departing Mon, Oct 13 from Portland to Naples, returning Mon, Nov 3, priced at $609 found 1 day ago
Delta
Sun, Nov 16 - Wed, Dec 3
PWM
Portland
NAP
Naples
$611 Roundtrip, found 2 days ago
$611
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Nov 16 from Portland to Naples, returning Wed, Dec 3, priced at $611 found 2 days ago
United
Mon, Dec 1 - Mon, Dec 15
PWM
Portland
NAP
Naples
$625 Roundtrip, found 2 days ago
$625
Roundtrip
found 2 days ago
Select United flight, departing Mon, Dec 1 from Portland to Naples, returning Mon, Dec 15, priced at $625 found 2 days ago
United
Mon, Dec 29 - Wed, Jan 14
PWM
Portland
NAP
Naples
$627 Roundtrip, found 3 days ago
$627
Roundtrip
found 3 days ago
Select United flight, departing Mon, Dec 29 from Portland to Naples, returning Wed, Jan 14, priced at $627 found 3 days ago
Air France
Sun, Nov 2 - Tue, Nov 11
PWM
Portland
NAP
Naples
$638 Roundtrip, found 1 day ago
$638
Roundtrip
found 1 day ago
Select Air France flight, departing Sun, Nov 2 from Portland to Naples, returning Tue, Nov 11, priced at $638 found 1 day ago
Air Canada
Wed, Oct 22 - Mon, Nov 10
PWM
Portland
NAP
Naples
$642 Roundtrip, found 1 day ago
$642
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Oct 22 from Portland to Naples, returning Mon, Nov 10, priced at $642 found 1 day ago
KLM
Mon, Dec 1 - Tue, Dec 16
PWM
Portland
NAP
Naples
$681 Roundtrip, found 2 days ago
$681
Roundtrip
found 2 days ago
Select KLM flight, departing Mon, Dec 1 from Portland to Naples, returning Tue, Dec 16, priced at $681 found 2 days ago

Alternative airports near Naples

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Naples Intl. NAP. Cheapest and Closest option available. Average driving time to city center is 10 minutes. Flights from $1,249
NAP
Naples Intl.
CheapestClosest
Average driving time to city center10 min
Flights from $1,249
Flights from Portland (PWM) to Naples (NAP)
Origin airport
Portland Intl. Jetport
Destination airport
Naples Intl.
Airlines serving
Air Canada, Air France, American Airlines, Austrian Airlines, Delta, KLM, TAP Portugal, Turkish Airlines, United
Roundtrip price
$593
Distance
4130 mi

Portland to Naples Flights

The cheapest times to fly from Portland to Naples

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Portland to Naples are during the month of October. You can find some of the cheapest flights from Portland to Naples with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Portland to Naples

Sunday is one of the best days to book for cheap flights from Portland to Naples: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Portland to Naples

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Portland to Naples in 2025. You can also book with separate airlines for your outbound and return journeys, from $463 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Portland to Naples flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Portland to Naples airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Portland Intl. Jetport Airport (PWM) to Naples Intl. Airport (NAP) cost?
Discover the latest flight deals from PWM to NAP by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from PWM to NAP?
The cheapest flights from PWM to NAP are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from PWM to NAP?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from PWM to NAP. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Portland Intl. Jetport Airport (PWM) to Naples Intl. Airport (NAP)?
You'll need to take a flight with a layover when traveling from Portland Intl. Jetport Airport (PWM) to Naples Intl. Airport (NAP). Direct flights don't operate daily on this route. However, just filter your search to include one or two stops to find the best option for your trip.
What day of the week has the most flights from PWM to NAP?
Typically you'll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* But this can change depending on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Portland Intl. Jetport Airport (PWM) to Naples Intl. Airport (NAP)?
To avoid potential delays on the Portland Intl. Jetport Airport (PWM) to Naples Intl. Airport (NAP) route, travel before 3 PM. Later flights have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Portland Intl. Jetport Airport (PWM) to Naples Intl. Airport (NAP) last-minute?
Last-minute fares from PWM to NAP are generally more expensive. To secure the cheapest rates, start looking for flights early. That being said, if you're flexible with your travel dates, you may land a cheap fare just before your departure.
Is it cheaper to book a PWM to NAP flight and hotel package?
You'll generally save money by securing a PWM to NAP flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. After choosing your preferred flights and accommodations, consider adding extras such as activities, tours and car rentals.
Can I cancel or change the date of my flight from Portland Intl. Jetport Airport (PWM) to Naples Intl. Airport (NAP)?
If you reserved your PWM to NAP flight within the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of fare you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more information.

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*Available to One Key members.