Cheap flights from Italy to Chicago from $333

The month of September is, on average, the cheapest month to fly to Chicago from Italy, with most prices found around $687. If you’re not able to fly to Chicago in September, then November is your next best option. Flight prices from Italy to Chicago during November average around $720.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $749. 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 $1,070.

Fly from Milan Malpensa 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 $786 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.

There are 3 cabin classes available to choose from on Italy to Chicago 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 Italy to Chicago.

Air Serbia, TAP AIR PORTUGAL, and Finnair 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 57% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 20% 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 in the early afternoon 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 September 2026, 19 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 September 2026, 138 flights take off from Italy and land in Chicago each week. The most common flight departure day for this route is Wed, with 16% of weekly flights taking off on this day.