Cheap flights from Chicago to Naples from $255

The cheapest month to fly to Naples from Chicago is in February. Flight prices, which tend to average around $614, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of February, then book flights to Naples from Chicago during March instead. Flights to Naples in March, while not as cheap as those in February, still average around $618.

Our data shows that Monday is the least expensive day to fly to Naples. Tickets to fly out on this day can be as low as $1,058. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Naples for around $1,257.

Our data shows that the cheapest Chicago to Naples flights are usually those with departure times in the afternoon. Our users have found flights to Naples in the afternoon for as low as $1,189. In the evening is when there is more demand to fly to Naples, so prices are often more expensive at around $1,415 per ticket.

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

You are more likely to see cheaper flights to Naples from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Naples for around $886 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Naples from Chicago for as low as $772 on momondo.

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

British Airways, Lufthansa, and KLM are the most popular carriers operating from Chicago to Naples

American Airlines, Iberia and Turkish Airlines are the top three most popular airlines that fly to Naples from Chicago according to our data. American Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Naples. Keep in mind that there are 9 different airlines that fly to Naples on a routine basis, so you have a few additional options to choose from.

Historically, on average around 31% of flights between Chicago and Naples have experienced a delay on any given week. The average delay length over the past 12 months has been 158 minutes.

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Thursday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 31% of their flights experiencing any sort of delay.

Istanbul (IST) was the most common stop: 53% of momondo users choosing 1-stop flights on this route connected there.

Flights via Dublin (DUB) offer the lowest average round-trip price of $697.

Flights connecting via Zurich (ZRH) have the shortest average one-way travel time: 11h 25m.

Zurich (ZRH) has the shortest average layover time for this route: 1h 18m.

2 flights are operational daily from Chicago to Naples as of October 2026. The most popular departure time for this route is 5:00PM, with 100% of flights per day taking off in the afternoon.

As of October 2026, there are 20 flights per week flying from Chicago to Naples. The most common day of the week flights depart is Mon, with 20% of flights taking off on this day.