Cheap flights from Milan to Chicago from $371

The month of February is, on average, the cheapest month to fly to Chicago from Milan, with most prices found around $686. If you’re not able to fly to Chicago in February, then November is your next best option. Flight prices from Milan to Chicago during November average around $705.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $708. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Milan to Chicago for around $966.

Fly from Milan Malpensa to Chicago O'Hare Intl for the best Milan - Chicago flight prices

There is only 1 cabin class available to choose from on Milan to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Historically, on average around 21% of flights between Milan and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 230 minutes.

Generally, flights departing in the morning 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. Tuesday 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 19% of their flights experiencing any sort of delay.

Copenhagen (CPH) was the most common stop: 44% of momondo users choosing 1-stop flights on this route connected there.

Flights via Copenhagen (CPH) offer the lowest average round-trip price of $621.

Flights connecting via Frankfurt am Main (FRA) have the shortest average one-way travel time: 11h 45m.

Frankfurt am Main (FRA) has the shortest average layover time for this route: 1h 20m.

As of September 2026, 3 flights take off from Milan and land in Chicago each day. The most common flight departure time for this route is 3:00PM, with 100% of daily flights taking off in the afternoon.

23 flights are operational weekly from Milan to Chicago as of September 2026. The most popular departure day for this route is Thu, with 22% of flights per week taking off on this day.