$452 Cheap Flights from Madison (MSN) to Naples (NAP)

View $452 flight on Sat, Jan 17, 2026Opens in a new window

Popular airlines from Dane County Regional Airport (MSN) to Naples Intl. Airport (NAP)

Cheap Flights from Madison to Naples (MSN-NAP)

Prices were available within the past 7 days and start at $452 for one-way flights and $576 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Jan 19 - Wed, Jan 28
MSN
Madison
NAP
Naples
$576 Roundtrip, found 6 days ago
$576
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Jan 19 from Madison to Naples, returning Wed, Jan 28, priced at $576 found 6 days ago
British Airways
Wed, Jan 14 - Thu, Jan 22
MSN
Madison
NAP
Naples
$581 Roundtrip, found 6 days ago
$581
Roundtrip
found 6 days ago
Select British Airways flight, departing Wed, Jan 14 from Madison to Naples, returning Thu, Jan 22, priced at $581 found 6 days ago
British Airways
Tue, Jan 20 - Mon, Jan 26
MSN
Madison
NAP
Naples
$589 Roundtrip, found 8 hours ago
$589
Roundtrip
found 8 hours ago
Select British Airways flight, departing Tue, Jan 20 from Madison to Naples, returning Mon, Jan 26, priced at $589 found 8 hours ago
Delta
Wed, Jan 14 - Wed, Jan 28
MSN
Madison
NAP
Naples
$594 Roundtrip, found 6 days ago
$594
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 14 from Madison to Naples, returning Wed, Jan 28, priced at $594 found 6 days ago
British Airways
Tue, Jan 20 - Mon, Jan 26
MSN
Madison
NAP
Naples
$594 Roundtrip, found 8 hours ago
$594
Roundtrip
found 8 hours ago
Select British Airways flight, departing Tue, Jan 20 from Madison to Naples, returning Mon, Jan 26, priced at $594 found 8 hours ago
British Airways
Tue, Jan 20 - Mon, Jan 26
MSN
Madison
NAP
Naples
$600 Roundtrip, found 8 hours ago
$600
Roundtrip
found 8 hours ago
Select British Airways flight, departing Tue, Jan 20 from Madison to Naples, returning Mon, Jan 26, priced at $600 found 8 hours ago
British Airways
Tue, Jan 20 - Mon, Jan 26
MSN
Madison
NAP
Naples
$605 Roundtrip, found 8 hours ago
$605
Roundtrip
found 8 hours ago
Select British Airways flight, departing Tue, Jan 20 from Madison to Naples, returning Mon, Jan 26, priced at $605 found 8 hours ago
Iberia
Tue, Jan 20 - Mon, Jan 26
MSN
Madison
NAP
Naples
$698 Roundtrip, found 8 hours ago
$698
Roundtrip
found 8 hours ago
Select Iberia flight, departing Tue, Jan 20 from Madison to Naples, returning Mon, Jan 26, priced at $698 found 8 hours ago
American Airlines
Fri, Oct 17 - Mon, Oct 20
MSN
Madison
NAP
Naples
$758 Roundtrip, found 3 days ago
$758
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Oct 17 from Madison to Naples, returning Mon, Oct 20, priced at $758 found 3 days ago
Lufthansa
Tue, Jan 20 - Mon, Jan 26
MSN
Madison
NAP
Naples
$869 Roundtrip, found 8 hours ago
$869
Roundtrip
found 8 hours ago
Select Lufthansa flight, departing Tue, Jan 20 from Madison to Naples, returning Mon, Jan 26, priced at $869 found 8 hours 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 $660
NAP
Naples Intl.
CheapestClosest
Average driving time to city center10 min
Flights from $660
Flights from Madison (MSN) to Naples (NAP)
Origin airport
Dane County Regional
Destination airport
Naples Intl.
Airlines serving
Air France, American Airlines, British Airways, Delta, Iberia, KLM, Lufthansa, United
Roundtrip price
$576
Distance
4939 mi

Madison to Naples Flights

The cheapest times to fly from Madison 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 Madison to Naples are during the month of January. You can find some of the cheapest flights from Madison to Naples with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Madison to Naples

Sunday is one of the best days to book for cheap flights from Madison 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 Madison 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 Madison to Naples in 2025. You can also book with separate airlines for your outbound and return journeys, from $452 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 Madison 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 Madison 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 Dane County Regional Airport (MSN) to Naples Intl. Airport (NAP) cost?
Get a cheap one-way flight from $452 or cheap return flight from $576 from Dane County Regional Airport (MSN) to Naples Intl. Airport (NAP) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Dane County Regional Airport (MSN) to Naples Intl. Airport (NAP)?
January is the most affordable month to fly from MSN to NAP. Timing your trip outside of the busy season is often the key to finding a great deal.
What is the cheapest airline that flies from Dane County Regional Airport (MSN) to Naples Intl. Airport (NAP)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll take you from MSN to NAP. Then, sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Dane County Regional Airport (MSN) to Naples Intl. Airport (NAP)?
There aren't any daily nonstop flights from Dane County Regional Airport (MSN) to Naples Intl. Airport (NAP). But you can opt for flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from MSN to NAP?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Dane County Regional Airport (MSN) to Naples Intl. Airport (NAP)?
To avoid potential delays on the Dane County Regional Airport (MSN) to Naples Intl. Airport (NAP) route, aim to fly before 3 PM. Later departures are 22% more likely to be canceled.**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 Dane County Regional Airport (MSN) to Naples Intl. Airport (NAP) last-minute?
Waiting until right before your break to book your flight from MSN to NAP often results in higher prices. While you may come across some last-minute deals, there's no guarantee. Be flexible with your travel plans for the best chance of landing a bargain.
Is it cheaper to book a MSN to NAP flight and hotel package?
You'll generally save money by securing a MSN 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 easy to manage it all in one convenient place. Once you've chosen your ideal accommodations and flights, you can add extras such as activities, car rentals and tours.
Can I cancel or change the date of my flight from Dane County Regional Airport (MSN) to Naples Intl. Airport (NAP)?
If you booked your MSN to NAP flight in the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the fare type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you'd like more information.

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*Available to One Key members.