How much is a ticket from Chicago Midway to Milan?

Depending on when you travel and how far in advance you book, fares between Chicago and Milan can differ a lot.

Choose a date to explore the best fares now.

If you’re flexible with timing, consider overnight flights — they often cost less and are less crowded. Exploring multiple date and time combinations can help you find the cheapest solution.

Which departure and arrival airports are available?

Between Chicago and Milan, flight options may depend on the combination of airports available.

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

Sometimes flying into a nearby city can be more cost-effective. When a city has multiple airports, it’s worth comparing different flight combinations.

Plan smarter: flights from Chicago Midway to Milan

Find the flight that fits your plans with Jetcost. You can filter results by stops, agencies, budget, time of day, and airline — all in one search.

Other popular destinations

Travelers flying to Italy also checked out: Catania, Milan, Naples, Palermo, Rome.

Comparing offers from multiple agencies helps you find the best price for the same route. You can also spot exclusive deals from individual airlines right in the results list.