How much should you expect to spend for a flight from Chicago to Milan?

Flight prices from Chicago to Milan change depending on demand and time of booking.

$499 is the lowest fare found in the past 15 days.

Studies show that flying midweek — like on a Tuesday or Wednesday — can be cheaper than weekend flights. Still, airfares change frequently, so check updated prices on Jetcost.

Airport options between Chicago and Milan

Even for routes around 4533 mi, using different airports might affect flight cost and travel time.

• Airports in Chicago: You can fly from 3 airports in Chicago - Midway, O'Hare, Rockford.
• Airports in Milan: Milan offers flights from 3 airports - Bergamo Orio al Serio, Linate, Malpensa.

Checking the average travel time to the airport can help you plan better. For some routes, changing your arrival or departure airport might also affect the price.

Match your flight search to your preferences: Chicago – Milan

Jetcost makes it easy to find the right flight. Set filters for flight time, price, number of stops, and preferred airline. You’ll see offers from Expedia, Delta, United, American, and more.

Other popular destinations

Thinking about traveling to Italy? Other users also viewed: Catania, Milan, Naples, Palermo, Rome.

Don’t forget to check change or cancellation policies, especially if your plans aren’t final. For a more targeted search, you can also set price limits directly in the filters.