Find out what a flight from Chicago Midway to Milan might cost

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

Select your dates to check current offers.

Try shifting your departure forward or backward by a day to find better options. If you’re looking for a good deal, consider flying outside peak hours as well.

Exploring all airports near Chicago and Milan

Checking all the airports available in the area can give you more departure and arrival options for your trip.

• Airports in Chicago: 3 different airports operate in Chicago - Midway, O'Hare, Rockford.
• Airports in Milan: Milan is served by 3 airports - Bergamo Orio al Serio, Linate, Malpensa.

Looking at expected traffic to the airport can help avoid surprises on departure day. On busy routes, flying from a quieter airport might also save you money.

Explore flights from Chicago Midway to Milan your way

On Jetcost, you can filter by round-trip or one-way, time of day, airline, number of stops, and even by specific travel agency.

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.