Cheap flights from Rome to Chicago from $499

The month of September is, on average, the cheapest month to fly to Chicago from Rome, with most prices found around $665. If you’re not able to fly to Chicago in September, then November is your next best option. Flight prices from Rome to Chicago during November average around $686.

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 Rome to Chicago for around $1,070.

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

You are more likely to see cheaper flights to Chicago from Rome 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 Rome for as low as $596 on momondo.

There are 3 cabin classes available to choose from on Rome to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

As of August 2026, prices for Rome to Chicago flights are approximately 9% cheaper when compared to flights at the same time last year.

TAP AIR PORTUGAL and Delta are the most popular carriers operating from Rome to Chicago

United Airlines, American Airlines and ITA Airways are the top three most popular airlines that fly to Chicago from Rome according to our data. United Airlines is the first choice among our users, with 52% 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 Rome and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 175 minutes.

Generally, flights departing in the evening tend to experience fewer delays. Flights in the morning 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.

Dublin (DUB) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Reykjavik (KEF) offer the lowest average round-trip price of $676.

Flights connecting via Reykjavik (KEF) have the shortest average one-way travel time: 12h 55m.

Reykjavik (KEF) has the shortest average layover time for this route: 1h 18m.

The number of flights available between Rome and Chicago is 12 per day as of August 2026. The most frequent departure time is 9:00AM, with 91% of daily flights leaving at noon.

85 flights are operational weekly from Rome to Chicago as of August 2026. The most popular departure day for this route is Tue, with 15% of flights per week taking off on this day.