Cheap flights from Milan to Chicago from $355

The month of December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Milan averaging around $731.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Tuesday when prices can be found for as low as $694. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Milan because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $989.

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

There is only 1 cabin class available to choose from on Milan to Chicago O'Hare Intl Airport 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 17% 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 231 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 13% of their flights experiencing any sort of delay.

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

Flights via Dublin (DUB) offer the lowest average round-trip price of $730.

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 33m.

The number of flights available between Milan and Chicago O'Hare Intl Airport is 5 per day as of October 2026. The most frequent departure time is 3:00PM, with 100% of daily flights leaving in the afternoon.

As of October 2026, 35 flights take off from Milan and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.