Cheap flights from Chicago O'Hare Intl Airport to Milan from $311

In general, April is the cheapest month to fly from Chicago O'Hare Intl Airport to Milan Malpensa Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $498. If you don’t want to visit Milan Malpensa Airport in April, then you should wait until January to fly from Chicago O'Hare Intl Airport, when ticket prices are also cheap, with an average price of $556.

Our data shows that Tuesday is the least expensive day to fly to Milan Malpensa Airport. Tickets to fly out on this day can be as low as $1,251. On the other hand, Sunday is the most expensive day to depart from Chicago O'Hare Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,585.

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

You are more likely to see cheaper flights to Milan Malpensa Airport from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Milan Malpensa Airport for around $886 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milan Malpensa Airport from Chicago O'Hare Intl Airport for as low as $850 on momondo.

There are 4 cabin classes available to choose from on Chicago O'Hare Intl Airport to Milan Malpensa Airport 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 32% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Milan Malpensa Airport flight.

Air Serbia is the most popular carrier operating from Chicago O'Hare Intl to Milan Malpensa

United Airlines, Scandinavian Airlines and TAP AIR PORTUGAL are the top three most popular airlines that fly to Milan Malpensa Airport from Chicago O'Hare Intl Airport according to our data. United Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Milan Malpensa Airport. Keep in mind that there are 4 different airlines that fly to Milan Malpensa Airport on a routine basis, so you have a few additional options to choose from.

Lisbon (LIS) was the most common stop: 38% of momondo users choosing 1-stop flights on this route connected there.

Flights via Lisbon (LIS) offer the lowest average round-trip price of $470.

Flights connecting via Frankfurt am Main (FRA) have the shortest average one-way travel time: 11h 58m.

Belgrade (BEG) has the shortest average layover time for this route: 1h 28m.

As of September 2026, 4 flights take off from Chicago O'Hare Intl Airport and land in Milan Malpensa Airport each day. The most common flight departure time for this route is 9:00PM, with 100% of daily flights taking off in the evening.

As of September 2026, 33 flights take off from Chicago O'Hare Intl Airport and land in Milan Malpensa Airport each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.