Cheap flights from Naples to Chicago from $367

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as $712. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Naples because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,620.

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

There are 2 cabin classes available to choose from on Naples to Chicago O'Hare Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Naples to Chicago O'Hare Intl Airport.

Historically, on average around 22% of flights between Naples and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 237 minutes.

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

Sunday 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 22% of their flights experiencing any sort of delay.

Rome (FCO) was the most common stop: 33% of momondo users choosing 1-stop flights on this route connected there.

Flights via Copenhagen (CPH) offer the lowest average round-trip price of $776.

Flights connecting via Rome (FCO) have the shortest average one-way travel time: 13h 35m.

Rome (FCO) has the shortest average layover time for this route: 2h 05m.

As of August 2026, 4 flights take off from Naples and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 3:00PM, with 100% of daily flights taking off in the afternoon.

28 flights are operational weekly from Naples to Chicago O'Hare Intl Airport as of August 2026. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.