Cheap flights from Chicago O'Hare Intl Airport to Milan from $273

The month of January is, on average, the cheapest month to fly to Milan from Chicago O'Hare Intl Airport, with most prices found around $556. The month of February is another great option to travel to Milan, with average flight prices from Chicago O'Hare Intl Airport averaging around $621.

Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,288. The most expensive day to fly to Milan is Sunday, with ticket prices averaging around $1,574.

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

You are more likely to see cheaper flights to Milan from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Milan for around $888 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milan 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 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 31% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Milan flight.

Aer Lingus, Turkish Airlines, and Scandinavian Airlines are the most popular carriers operating from Chicago O'Hare Intl to Milan

United Airlines, Scandinavian Airlines and TAP AIR PORTUGAL are the top three most popular airlines that fly to Milan 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. Keep in mind that there are 5 different airlines that fly to Milan on a routine basis, so you have a few additional options to choose from.

Copenhagen (CPH) was the most common stop: 30% 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.

Rome (FCO) has the shortest average layover time for this route: 1h 25m.

As of September 2026, 4 flights take off from Chicago O'Hare Intl Airport and land in Milan 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, 30 flights take off from Chicago O'Hare Intl Airport and land in Milan each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.