$375 Cheap Flights from Winnipeg (YWG) to Naples (NAP)

View $375 flight on Wed, Oct 1, 2025Opens in a new window

Popular airlines from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Naples Intl. Airport (NAP)

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Winnipeg to Naples (YWG-NAP)

Prices were available within the past 7 days and start at $375 for one-way flights and $844 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Lufthansa
Tue, Sep 16 - Thu, Sep 25
YWG
Winnipeg
NAP
Naples
$844 Roundtrip, found 2 days ago
$844
Roundtrip
found 2 days ago
Select Lufthansa flight, departing Tue, Sep 16 from Winnipeg to Naples, returning Thu, Sep 25, priced at $844 found 2 days ago
Lufthansa
Tue, Sep 16 - Thu, Sep 25
YWG
Winnipeg
NAP
Naples
$850 Roundtrip, found 2 days ago
$850
Roundtrip
found 2 days ago
Select Lufthansa flight, departing Tue, Sep 16 from Winnipeg to Naples, returning Thu, Sep 25, priced at $850 found 2 days ago
Air Canada
Tue, Sep 16 - Thu, Sep 25
YWG
Winnipeg
NAP
Naples
$855 Roundtrip, found 2 days ago
$855
Roundtrip
found 2 days ago
Select Air Canada flight, departing Tue, Sep 16 from Winnipeg to Naples, returning Thu, Sep 25, priced at $855 found 2 days ago
Air Canada
Tue, Sep 16 - Thu, Sep 25
YWG
Winnipeg
NAP
Naples
$861 Roundtrip, found 2 days ago
$861
Roundtrip
found 2 days ago
Select Air Canada flight, departing Tue, Sep 16 from Winnipeg to Naples, returning Thu, Sep 25, priced at $861 found 2 days ago
Air Canada
Tue, Sep 16 - Thu, Sep 25
YWG
Winnipeg
NAP
Naples
$866 Roundtrip, found 2 days ago
$866
Roundtrip
found 2 days ago
Select Air Canada flight, departing Tue, Sep 16 from Winnipeg to Naples, returning Thu, Sep 25, priced at $866 found 2 days ago
Air Canada
Tue, Sep 16 - Thu, Sep 25
YWG
Winnipeg
NAP
Naples
$872 Roundtrip, found 2 days ago
$872
Roundtrip
found 2 days ago
Select Air Canada flight, departing Tue, Sep 16 from Winnipeg to Naples, returning Thu, Sep 25, priced at $872 found 2 days ago
Air Canada
Tue, Sep 16 - Thu, Sep 25
YWG
Winnipeg
NAP
Naples
$877 Roundtrip, found 2 days ago
$877
Roundtrip
found 2 days ago
Select Air Canada flight, departing Tue, Sep 16 from Winnipeg to Naples, returning Thu, Sep 25, priced at $877 found 2 days ago
Lufthansa
Tue, Sep 16 - Thu, Sep 25
YWG
Winnipeg
NAP
Naples
$883 Roundtrip, found 2 days ago
$883
Roundtrip
found 2 days ago
Select Lufthansa flight, departing Tue, Sep 16 from Winnipeg to Naples, returning Thu, Sep 25, priced at $883 found 2 days ago
TAP Portugal
Tue, Sep 16 - Thu, Sep 25
YWG
Winnipeg
NAP
Naples
$1,830 Roundtrip, found 2 days ago
$1,830
Roundtrip
found 2 days ago
Select TAP Portugal flight, departing Tue, Sep 16 from Winnipeg to Naples, returning Thu, Sep 25, priced at $1,830 found 2 days ago
WestJet
Tue, Sep 16 - Thu, Sep 25
YWG
Winnipeg
NAP
Naples
$2,120 Roundtrip, found 2 days ago
$2,120
Roundtrip
found 2 days ago
Select WestJet flight, departing Tue, Sep 16 from Winnipeg to Naples, returning Thu, Sep 25, priced at $2,120 found 2 days ago
Flights from Winnipeg (YWG) to Naples (NAP)
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
Naples Intl.
Roundtrip price
$843
Distance
4919 mi

Winnipeg to Naples Flights

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

 

The best time to book a flight from Winnipeg to Naples

Sunday is one of the best days to book for cheap flights from Winnipeg 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 Winnipeg 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 Winnipeg to Naples in 2025. You can also book with separate airlines for your outbound and return journeys, from $375 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 Winnipeg 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 Winnipeg 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 Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Naples Intl. Airport (NAP) cost?
Discover the latest flight deals from YWG 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 YWG to NAP?
The cheapest flights from YWG 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 YWG to NAP?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from YWG to NAP. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Naples Intl. Airport (NAP)?
There are no daily nonstop flights departing from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Naples Intl. Airport (NAP). But you can choose flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be on your way in no time.
What day of the week has the most flights from YWG to NAP?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change 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 Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Naples Intl. Airport (NAP)?
Book a flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Naples Intl. Airport (NAP) that takes off before 3 PM to reduce the risk of cancellations and delays. Departures after this hour are on average 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 Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Naples Intl. Airport (NAP) last-minute?
Booking your flight from YWG to NAP shortly before your getaway is usually more expensive. But if there's some wiggle room with your departure dates and times, you could snag a cheap last-minute fare.
Is it cheaper to book a YWG to NAP flight and hotel package?
Booking a YWG to NAP flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Select from our impressive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Naples Intl. Airport (NAP)?
It's generally possible to reschedule or cancel your YWG to NAP flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more details on our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.