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

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

Flights from Naples (APF) to Chicago (MDW)
Origin airport
Naples Municipal
Destination airport
Midway Intl.
Distance
1132 mi

Naples to Chicago Flights

The cheapest times to fly from Naples to Chicago

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

 

The best time to book a flight from Naples to Chicago

Sunday is one of the best days to book for cheap flights from Naples to Chicago: 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 Naples to Chicago

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 Naples to Chicago 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 Naples to Chicago 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 Naples to Chicago 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 Naples Municipal Airport (APF) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight or cheap return flight from Naples Municipal Airport (APF) to Midway Intl. Airport (MDW) 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 Naples Municipal Airport (APF) to Midway Intl. Airport (MDW)?
is the most affordable month to fly from APF to MDW. Traveling during an off-peak travel window is often the key to scoring lower fares.
Which airlines fly direct from Naples Municipal Airport (APF) to Midway Intl. Airport (MDW)?
You can't catch a nonstop flight to Midway Intl. Airport (MDW) from Naples, FL (APF-Naples Municipal). However, you can arrive in Chicago without any layovers by departing from Southwest Florida Intl. Airport (RSW).
What is the cheapest airline that flies from Naples Municipal Airport (APF) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare different airlines and find the cheapest carrier that'll take you from APF to MDW. Then, sort your results by "Price (lowest to highest)" to score a great deal.
How many flights per day from Naples Municipal Airport (APF) to Midway Intl. Airport (MDW)?
There are no daily direct flights available from Naples Municipal Airport (APF) to Midway Intl. Airport (MDW). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from APF to MDW?
Typically you'll find the most flight options available on a Friday. Tuesdays are often the quietest.* But this can change based on the season, carrier 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 Naples Municipal Airport (APF) to Midway Intl. Airport (MDW)?
To touch down at Midway Intl. Airport (MDW) without delays, opt for a flight that leaves Naples Municipal Airport (APF) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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 Naples Municipal Airport (APF) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from APF to MDW shortly before your journey is typically more expensive. But if there's some wiggle room with your departure times and dates, you could score a cheap last-minute fare.
Is it cheaper to book an APF to MDW flight and hotel package?
Opting for an APF to MDW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Choose from our wide range of stays and then add activities, flights and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Naples Municipal Airport (APF) to Midway Intl. Airport (MDW)?
Typically, you're able to reschedule or cancel your APF to MDW flight. However, there may be additional fees, especially if you booked over 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you need more information, head to our Customer Service portal.

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*Available to One Key members.