Cheap flights from Milan to Chicago from £280

The cheapest month to fly to Chicago from Milan is in February. Flight prices, which tend to average around £458, 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 March instead. Flights to Chicago in March, while not as cheap as those in February, still average around £467.

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 £657 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Milan for as low as £396 on momondo.

There are 2 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.

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

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 22% 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 209 minutes.

Generally, flights departing in the morning 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 21% of their flights experiencing any sort of delay.