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

Popular airlines from Chicago Midway Airport (MDW) to Naples, FL (APF-Naples Municipal)

Alternative airports near Naples

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

Select flight to Southwest Florida Intl. RSW. Cheapest option available. Average driving time to city center is 39 minutes. Flights from $419
RSW
Southwest Florida Intl.
Cheapest
Average driving time to city center39 min
Flights from $419

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Naples Municipal Airport (APF) cost?
Lock in a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Naples Municipal Airport (APF) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Naples Municipal Airport (APF)?
The cheapest month to fly from MDW to APF is , when there's less demand. Off-peak season is usually when you'll find cheap fares for travel between these airports.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Naples Municipal Airport (APF)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest MDW to APF flight.
How many flights per day from Midway Intl. Airport (MDW) to Naples Municipal Airport (APF)?
There are no daily direct flights departing from Midway Intl. Airport (MDW) to Naples Municipal Airport (APF). But you can opt for flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be cruising above the clouds before you know it.
What day of the week has the most flights from MDW to APF?
Typically you'll find the most flight options available on a Friday. Tuesdays are often the quietest.* However, this can vary based on the airline, season 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 Midway Intl. Airport (MDW) to Naples Municipal Airport (APF)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Naples Municipal Airport (APF) route, travel before 3 PM. Departures after this hour have a 22% higher chance of being 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.
What airports do you fly into for Naples from Midway Intl. Airport (MDW)?
If you're departing on a direct flight from Midway Intl. Airport (MDW) to Naples, you can land at either Southwest Florida Intl. Airport (RSW) or Charlotte County Airport (PGD).
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Naples Municipal Airport (APF) last-minute?
Holding off until right before your break to book a flight from MDW to APF often results in higher prices. While it's possible to find some last-minute deals, they're not always guaranteed. Be flexible with your travel plans for a better chance of landing a bargain.
Is it cheaper to book a MDW to APF flight and hotel package?
You'll generally save money by securing a MDW to APF 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 everything in one place. After choosing your ideal flights and accommodations, consider other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Naples Municipal Airport (APF)?
It's generally possible to reschedule or cancel your MDW to APF flight. However, if it's been more than 24 hours since booking, additional fees may apply. Check 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.

Travel information

Origin airport
Midway Intl.
Destination airport
Naples Municipal
Distance
1132 mi

Book with confidence

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.

 

Chicago to Naples Flights

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*Available to One Key members.