Cheap flights from Chicago to Italy from $264

The cheapest month to fly to Italy from Chicago is in February. Flight prices, which tend to average around $644, 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 Italy from Chicago during January instead. Flights to Italy in January, while not as cheap as those in February, still average around $664.

According to our data, Sunday is the cheapest day to fly to Italy from Chicago. The lowest ticket price found for a Sunday departure recently was $951. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Italy for around $1,056.

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

You are more likely to see cheaper flights to Italy from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Italy for around $855 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Italy from Chicago for as low as $772 on momondo.

There are 4 cabin classes available to choose from on Chicago to Italy flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 52% on your flight if you consider stops on a Chicago to Italy flight.

United Airlines, TAP AIR PORTUGAL, and Air Serbia are the most popular carriers operating from Chicago to Italy

United Airlines, ITA Airways and Lufthansa are the top three most popular airlines that fly to Italy from Chicago according to our data. United Airlines is the first choice among our users, with 33% of people opting to fly with this airline when traveling to Italy. Keep in mind that there are 15 different airlines that fly to Italy on a routine basis, so you have a few additional options to choose from.

Historically, on average around 30% of flights between Chicago and Italy have experienced a delay on any given week. The average delay length over the past 12 months has been 160 minutes.

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

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

According to our data, ITA Airways have had the least number of delays on this route over the last 12 months; with about 29% of their flights experiencing any sort of delay.

13 flights are operational daily from Chicago to Italy as of October 2026. The most popular departure time for this route is 4:00PM, with 70% of flights per day taking off in the afternoon.

As of October 2026, there are 96 flights per week flying from Chicago to Italy. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.