Flight prices from Chicago Midway to Milan Malpensa

There’s no fixed price — fares between Chicago and Milan can vary a lot by day or time.

Choose a date to explore the best fares now.

The lowest fares are often found with some flexibility in travel dates. If your plans are flexible, you’ll have a better chance of finding cheap flights.

Which airports near Chicago or Milan offer flights?

In many cases, using a nearby airport can improve your chances of finding direct flights or better rates.

• Airports in Chicago: 3 airports are active - Midway, O'Hare, Rockford.
• Airports in Milan: 3 options available in Milan - Bergamo Orio al Serio, Linate, Malpensa.

Secondary airports can offer faster travel thanks to shorter lines and quicker boarding times than major ones.

Flight filters for the route Chicago Midway – Milan Malpensa

Customize your search on Jetcost to focus only on flights that suit your needs. Whether you want a direct connection, specific airline, or shorter layover, filters help you find it faster.

Other popular destinations

Flights to Italy are often searched alongside: Catania, Milan, Naples, Palermo, Rome.

The cheapest flights might leave at odd hours or arrive at less central airports — keep that in mind. If you travel often, you can always select your trusted airlines from the available options.