Cheap flights from Italy to Chicago from $300

The month of September is, on average, the cheapest month to fly to Chicago from Italy, with most prices found around $404. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from Italy to Chicago during May average around $426.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $752. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Italy to Chicago for around $965.

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

You are more likely to see cheaper flights to Chicago from Italy when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $789 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Italy for as low as $596 on momondo.

Icelandair, American Airlines, and Aer Lingus are the most popular carriers operating from Italy to Chicago

United Airlines, ITA Airways and American Airlines are the top three most popular airlines that fly to Chicago from Italy according to our data. United Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 22% of flights between Italy and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 193 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.

Thursday 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, Ethiopian Air have had the least number of delays on this route over the last 12 months; with about 17% of their flights experiencing any sort of delay.

As of July 2026, 21 flights take off from Italy and land in Chicago each day. The most common flight departure time for this route is 3:00PM, with 53% of daily flights taking off at noon.

As of July 2026, 149 flights take off from Italy and land in Chicago each week. The most common flight departure day for this route is Wed, with 15% of weekly flights taking off on this day.