Cheap flights from Chicago O'Hare Intl Airport to Italy from $272

The cheapest month to fly to Italy from Chicago O'Hare Intl Airport is in January. Flight prices, which tend to average around $514, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Italy from Chicago O'Hare Intl Airport during November instead. Flights to Italy in November, while not as cheap as those in January, still average around $569.

According to our data, Monday is the cheapest day to fly to Italy from Chicago O'Hare Intl Airport. The lowest ticket price found for a Monday departure recently was $891. 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 Thursday, the most expensive travel day of the week, you can expect to see flight prices from Chicago O'Hare Intl Airport to Italy for around $1,015.

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

You are more likely to see cheaper flights to Italy from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Italy for around $781 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Italy from Chicago O'Hare Intl Airport for as low as $748 on momondo.

There are 3 cabin classes available to choose from on Chicago O'Hare Intl to Italy 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 Chicago O'Hare Intl Airport to Italy.

Air Serbia, British Airways, and TAP AIR PORTUGAL are the most popular carriers operating from Chicago O'Hare Intl to Italy

United Airlines, ITA Airways and Lufthansa are the top three most popular airlines that fly to Italy from Chicago O'Hare Intl Airport according to our data. United Airlines is the first choice among our users, with 31% of people opting to fly with this airline when traveling to Italy. Keep in mind that there are 17 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 165 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.

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

According to our data, United Airlines 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.

As of April 2026, 16 flights take off from Chicago O'Hare Intl Airport and land in Italy each day. The most common flight departure time for this route is 3:00PM, with 68% of daily flights taking off in the afternoon.

112 flights are operational weekly from Chicago O'Hare Intl Airport to Italy as of April 2026. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.