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

Popular airlines from Naples, FL (APF-Naples Municipal) to Chicago O'Hare Intl. Airport (ORD)

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Frequently asked questions

How much does a flight from Naples Municipal Airport (APF) to O'Hare Intl. Airport (ORD) cost?
Lock in a cheap one-way flight or cheap return flight from Naples Municipal Airport (APF) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Naples Municipal Airport (APF) to O'Hare Intl. Airport (ORD)?
is the most affordable month to fly from APF to ORD. Timing your trip outside of the busy season is often the key to scoring lower fares.
Which airlines fly direct from Naples Municipal Airport (APF) to O'Hare Intl. Airport (ORD)?
While Naples, FL (APF-Naples Municipal) has no direct flights to O'Hare Intl. Airport (ORD), other airports have nonstop options. Departing from Southwest Florida Intl. Airport (RSW) will get you to Chicago without any detours.
What is the cheapest airline that flies from Naples Municipal Airport (APF) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest APF to ORD flight.
How many flights per day from Naples Municipal Airport (APF) to O'Hare Intl. Airport (ORD)?
Direct flights from Naples Municipal Airport (APF) to O'Hare Intl. Airport (ORD) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from APF to ORD?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Remember that flight schedules can vary based on a range of factors, such as the carrier and season.*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 O'Hare Intl. Airport (ORD)?
To arrive at O'Hare Intl. Airport (ORD) on schedule, opt for a flight that takes off from Naples Municipal Airport (APF) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**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 O'Hare Intl. Airport (ORD) last-minute?
Booking your flight from APF to ORD right before your getaway is typically more expensive. However, 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 ORD flight and hotel package?
You'll generally save money by securing an APF to ORD flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After selecting your preferred accommodations and flights, you can add extras like car rentals, tours and activities.
Can I cancel or change the date of my flight from Naples Municipal Airport (APF) to O'Hare Intl. Airport (ORD)?
In most instances, you can cancel or reschedule your APF to ORD flight. However, there may be additional fees, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's policies and fees on flight changes, or if you'd like more information, visit our Customer Service portal.

Travel information

Origin airport
Naples Municipal
Destination airport
O'Hare Intl.
Distance
1147 mi

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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 2026. 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.

 

Naples to Chicago Flights

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*Available to One Key members.