Cheap flights from Chicago to Milan from $353

If you don’t have specific dates for your trip between Chicago and Milan, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.

Traveling between Chicago and Milan, you can choose between direct (nonstop) flights or flights with one or more stops. You can select the number of stops on your journey, including an overnight stopover, and the duration of the stopover. What’s more, you can also select where you want to have your stopover. Want to say "Hi" to a friend in another city en route to your destination? Or fancy a quick round of shopping? Go Multi-City or Nomad and add places to your search that you wish to visit.

There are a number of airports in and around Chicago. The main one is O Hare International and other nearby airports include Gerald R. Ford International, South Bend International, Dane County Regional, General Mitchell International, Fort Wayne International, General Wayne A. Downing Peoria International, Quad City International, Central Illinois Regional, Kalamazoo/Battle Creek International, University of Illinois Willard

There are a number of airports in and around Milan. The main one is Milan–Malpensa and other nearby airports include Venice Marco Polo, Zürich Airport, Florence, Bologna Guglielmo Marconi, Treviso, Pisa International, Turin, Verona Villafranca, Genoa Cristoforo Colombo, Parma.

This depends on the airline’s flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from Chicago, such as morning, afternoon, evening, or night, or select the exact hours for departure.

This depends on the airline’s flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Milan, such as morning, afternoon, evening, or night, or select the exact hours for arrival.

This depends on the airline’s flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from Chicago, such as morning, afternoon, evening, or night, or select the exact hours for departure.

This depends on the airline’s flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Milan, such as morning, afternoon, evening, or night, or select the exact hours for arrival.