Cheap flights from Chicago O'Hare Intl Airport to Naples from $344

The cheapest month to fly to Naples from Chicago O'Hare Intl Airport is in February. Flight prices, which tend to average around $549, 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 O'Hare Intl Airport during November instead. Flights to Naples in November, while not as cheap as those in February, still average around $590.

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 $871. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Chicago O'Hare Intl Airport to Naples for around $1,235.

Our data shows that the cheapest Chicago O'Hare Intl Airport 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 $872. In the afternoon is when there is more demand to fly to Naples, so prices are often more expensive at around $1,231 per ticket.

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

You are more likely to see cheaper flights to Naples from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Naples for around $802 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Naples from Chicago O'Hare Intl Airport for as low as $699 on momondo.

SWISS, TAP AIR PORTUGAL, and British Airways are the most popular carriers operating from Chicago O'Hare Intl to Naples

American Airlines, Turkish Airlines and British Airways are the top three most popular airlines that fly to Naples from Chicago O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 64% 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.

Historically, on average around 32% 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 174 minutes.

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

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday 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 32% of their flights experiencing any sort of delay.

Dublin (DUB) was the most common stop: 43% of momondo users choosing 1-stop flights on this route connected there.

Flights via Zurich (ZRH) offer the lowest average round-trip price of $737.

Flights connecting via Zurich (ZRH) have the shortest average one-way travel time: 11h 40m.

Zurich (ZRH) has the shortest average layover time for this route: 1h 24m.

As of May 2026, there are 3 flights per day flying from Chicago O'Hare Intl Airport to Naples. The most common time of day flights depart is 5:00PM, with 100% of flights taking off in the afternoon.

As of May 2026, there are 24 flights per week flying from Chicago O'Hare Intl Airport to Naples. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.