Cheap flights from Milan to Chicago from $345

The month of February is, on average, the cheapest month to fly to Chicago from Milan, with most prices found around $614. If you’re not able to fly to Chicago in February, then March is your next best option. Flight prices from Milan to Chicago during March average around $626.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $760. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Milan to Chicago for around $1,213.

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

You are more likely to see cheaper flights to Chicago from Milan when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $881 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Milan for as low as $531 on momondo.

There are 3 cabin classes 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.

As of March 2026, prices for Milan to Chicago flights are approximately 29% more expensive when compared to flights at the same time last year.

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 210 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, Qatar Airways have had the least number of delays on this route over the last 12 months; with about 21% of their flights experiencing any sort of delay.

Reykjavik (KEF) was the most common stop: 36% of momondo users choosing 1-stop flights on this route connected there.

Flights via Lisbon (LIS) offer the lowest average round-trip price of $400.

Flights connecting via Frankfurt am Main (FRA) have the shortest average one-way travel time: 12h 08m.

Rome (FCO) has the shortest average layover time for this route: 1h 10m.