Cheap Flights from Chicago (PWK) to Naples (APF)

Popular airlines from Chicago, IL (PWK-Chicago Executive) to Naples, FL (APF-Naples Municipal)

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Flights from Chicago (PWK) to Naples (APF)
Origin airport
Chicago Executive
Destination airport
Naples Municipal
Distance
1156 mi

Chicago to Naples Flights

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

 

The best time to book a flight from Chicago to Naples

Sunday is one of the best days to book for cheap flights from Chicago 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 Chicago 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 Chicago to Naples in 2025. You can also book with separate airlines for your outbound and return journeys, from 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 Chicago 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 Chicago 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 Chicago Executive Airport (PWK) to Naples Municipal Airport (APF) cost?
Discover the latest flight deals from PWK to APF 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 PWK to APF?
The cheapest flights from PWK to APF 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 PWK to APF?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from PWK to APF. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Chicago Executive Airport (PWK) to Naples Municipal Airport (APF)?
Nonstop flights from Chicago Executive Airport (PWK) to Naples Municipal Airport (APF) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel details and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from PWK to APF?
Generally you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* However, this can vary based 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 Chicago Executive Airport (PWK) to Naples Municipal Airport (APF)?
Select a flight from Chicago Executive Airport (PWK) to Naples Municipal Airport (APF) that takes off before 3 PM to reduce the risk of cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**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 Chicago Executive Airport (PWK) to Naples Municipal Airport (APF) last-minute?
Holding off until just before your trip to book a flight from PWK to APF often results in higher prices. While you may find some last-minute discounts, they're not always guaranteed. Keep your travel schedule open for the best chance of getting a bargain.
Is it cheaper to book a PWK to APF flight and hotel package?
Securing a PWK to APF flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Select from our extensive range of accommodations and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago Executive Airport (PWK) to Naples Municipal Airport (APF)?
If you booked your PWK to APF flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

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*Available to One Key members.