Cheap flights from Illinois to Naples from $317

The cheapest month to fly to Naples from Illinois is in May. Flight prices, which tend to average around $371, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of May, then book flights to Naples from Illinois during April instead. Flights to Naples in April, while not as cheap as those in May, still average around $398.

Our data shows that Sunday is the least expensive day to fly to Naples. Tickets to fly out on this day can be as low as $886. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Illinois to Naples for around $1,235.

Our data shows that the cheapest Illinois to Naples flights are usually those with departure times in the evening. Our users have found flights to Naples in the evening for as low as $886. In the afternoon is when there is more demand to fly to Naples, so prices are often more expensive at around $1,234 per ticket.

Fly from Chicago O'Hare Intl to Naples for the best Illinois - Naples flight prices

You are more likely to see cheaper flights to Naples from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Naples for around $820 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Naples from Illinois for as low as $737 on momondo.

There are 3 cabin classes available to choose from on Illinois to Naples flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

TAP AIR PORTUGAL, Delta, and Air Canada are the most popular carriers operating from Illinois to Naples

American Airlines, Turkish Airlines and British Airways are the top three most popular airlines that fly to Naples from Illinois according to our data. American Airlines is the first choice among our users, with 56% of people opting to fly with this airline when traveling to Naples. Keep in mind that there are 11 different airlines that fly to Naples on a routine basis, so you have a few additional options to choose from.

As of June 2026, there are 3 flights per day flying from Illinois to Naples. The most common time of day flights depart is 5:00PM, with 100% of flights taking off in the afternoon.

24 flights are operational weekly from Illinois to Naples as of June 2026. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.