Cheap flights from Milan Malpensa Airport to Chicago from $359

The month of February is, on average, the cheapest month to fly to Chicago from Milan Malpensa Airport, with most prices found around $516. If you’re not able to fly to Chicago in February, then November is your next best option. Flight prices from Milan Malpensa Airport to Chicago during November average around $683.

The cheapest day to depart on your flight to Chicago is on a Saturday 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 Malpensa Airport to Chicago for around $885.

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

There are 2 cabin classes available to choose from on Milan Malpensa Airport 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 23% 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 222 minutes.

Generally, flights departing in the early afternoon 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 22% of their flights experiencing any sort of delay.

Lisbon (LIS) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

Flights via Frankfurt am Main (FRA) offer the lowest average round-trip price of $850.

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.

5 flights are operational daily from Milan Malpensa Airport to Chicago as of August 2026. The most popular departure time for this route is 3:00PM, with 100% of flights per day taking off in the afternoon.

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