$372 Find Cheap Flights from Naples to Chicago - Compare and Save

If your flying dates are flexible, you should consider flying to Chicago on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from Naples to Chicago. For your return ticket, we recommend flying on a Sunday and avoiding Wednesdays for the best deals.

The cheapest month for flights from Naples to Chicago O'Hare Intl Airport is February, where tickets cost $0 (return) on average. On the other hand, the most expensive months are September and July, where the average cost of round-trip tickets is $1,036 and $1,011 respectively.

Weekly flights between Naples and Chicago historically see delays in approximately 21% of cases, with the average delay over the past year being 224 minutes.

Typically, flights leaving in the early afternoon tend to face fewer delays, whereas flights in the morning have historically encountered delays more often.

Statistically, Thursday is the day of the week with the fewest delays on this flight route, while Friday has typically experienced more delays than other days.

Based on our data, American Airlines have experienced the fewest delays on this route in the past 12 months, with only about 21% of their flights encountering any delays.

Dublin (DUB) is the top choice – 67% of KAYAK users who clicked on 1-stop flights from Naples to Chicago picked an itinerary connecting there.

Flights via Dublin (DUB) offer the most affordable fares, with an average round-trip price of $729.

Consider flying via Dublin (DUB) for the shortest journey. The average one-way travel time for flights connecting there is 14h 35m.

If you prefer a quick connection, Dublin (DUB) often has the shortest layovers from Naples to Chicago, with an average of 1h 53m.

There are 2 cabin class options for the route. These are Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

There is a maximum of 1 nonstop flight a day that takes off from Naples and lands in Chicago O'Hare Intl Airport, with an average flight time of 10h 45m. The most common departure time is 3:00 pm and most flights take off in the afternoon. Each week, there are 7 flights.