What’s the cost of a flight from Chicago Midway to Milan Linate?

Prices vary based on date, airline, and availability. Compare several options if you're flying between Chicago and Milan.

Choose a date to explore the best fares now.

If possible, avoid holiday periods: ticket prices tend to rise quickly and availability drops, especially on busy routes. Morning and evening flights are often in high demand too — book early to get a good fare.

Which airports are most convenient between Chicago and Milan?

Whether it’s cost or connection time, the right airport combination can make a difference.

• Airports in Chicago: There are 3 airports in Chicago - Midway, O'Hare, Rockford.
• Airports in Milan: In Milan you can fly to/from 3 airports - Bergamo Orio al Serio, Linate, Malpensa.

In some cases, flying into a secondary airport can also reduce transfer costs. Connections from multiple airports give you more flight options and airlines.

Explore flights from Chicago Midway to Milan Linate your way

On Jetcost, you can filter by round-trip or one-way, time of day, airline, number of stops, and even by agency like eDreams or Expedia. Options include Delta, United, American, and more.

Other popular destinations

Also interested in Italy? Check out: Catania, Milan, Naples, Palermo, Rome.

If you’re flexible with dates, try checking the days before and after to see if prices vary. Some routes are offered by multiple agencies — comparing fares can really pay off.