Cheap flights from Milan to Chicago from £375

The cheapest month to fly to Chicago from Milan is in February. Flight prices, which tend to average around £459, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of February, then book flights to Chicago from Milan during October instead. Flights to Chicago in October, while not as cheap as those in February, still average around £509.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as £554. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Friday, with ticket prices averaging around £748.

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.

You could potentially save up to 67% on your flight if you consider stops on a Milan to Chicago flight.

As of July 2026, prices for Milan to Chicago flights are approximately 12% cheaper when compared to flights at the same time last year.

Historically, on average around 25% 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 212 minutes.

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights departing in the evening have, in the past, seen delays more frequently in comparison.

Friday is statistically the day of the week that experiences the fewest 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 fewest delays on this route over the last 12 months, with about 24% of their flights experiencing any sort of delay.

5 flights are operational daily from Milan to Chicago as of July 2026. The most popular departure time for this route is 15:00, with 100% of flights per day taking off in the afternoon.

The number of flights available between Milan and Chicago is 35 per week as of July 2026. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.