Cheap flights from Chicago to Milan from $295

The month of February is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $580. The month of January is another great option to travel to Milan, with average flight prices from Chicago averaging around $585.

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 - Milan flight prices

You are more likely to see cheaper flights to Milan from Chicago 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 for as low as $850 on momondo.

There are 4 cabin classes available to choose from on Chicago 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 to Milan flight.

Aer Lingus, JetBlue, and Delta are the most popular carriers operating from Chicago to Milan

United Airlines, Scandinavian Airlines and TAP AIR PORTUGAL are the top three most popular airlines that fly to Milan from Chicago 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: 31% of momondo users choosing 1-stop flights on this route connected there.

Flights via Reykjavik (KEF) offer the lowest average round-trip price of $403.

Flights connecting via Madrid (MAD) have the shortest average one-way travel time: 11h 30m.

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

As of August 2026, there are 5 flights per day flying from Chicago to Milan. The most common time of day flights depart is 9:00PM, with 100% of flights taking off in the evening.

As of August 2026, there are 35 flights per week flying from Chicago to Milan. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.