Cheap flights from Naples to Chicago from $399

The month of November is, on average, the cheapest month to fly to Chicago from Naples, with most prices found around $481. If you’re not able to fly to Chicago in November, then September is your next best option. Flight prices from Naples to Chicago during September average around $554.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $741. This is often the case because there is less demand to fly during this day of the week. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Naples to Chicago for around $892.

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

Historically, on average around 23% 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 222 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.

Thursday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday 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 23% of their flights experiencing any sort of delay.

Copenhagen (CPH) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Copenhagen (CPH) offer the lowest average round-trip price of $628.

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.

4 flights are operational daily from Naples to Chicago as of May 2026. The most popular departure time for this route is 3:00PM, with 100% of flights per day taking off in the afternoon.

As of May 2026, there are 28 flights per week flying from Naples to Chicago. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.