Flights from Chicago to Milan available from USD 645*
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Our best rates from Chicago to Milan
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Fly in the next 3 months: flights from Chicago to Milan (MXP)
Icelandair airfare from Chicago to Milan - starting at USD 797
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USD
Chicago (ORD)to
Milan (MXP)Oct 05 2026 - Oct 13 2026
From
USD 797
Viewed 17 hrs ago
Round trip
Economy
Chicago (ORD)to
Milan (MXP)Oct 02 2026 - Oct 13 2026
From
USD 797
Viewed 17 hrs ago
Round trip
Economy
Chicago (ORD)to
Milan (MXP)Oct 03 2026 - Oct 13 2026
From
USD 797
Viewed 17 hrs ago
Round trip
Economy
Chicago (ORD)to
Milan (MXP)Oct 03 2026 - Oct 15 2026
From
USD 797
Viewed 17 hrs ago
Round trip
Economy
Chicago (ORD)to
Milan (MXP)Oct 05 2026 - Oct 15 2026
From
USD 797
Viewed 17 hrs ago
Round trip
Economy
*Fares displayed have been collected within the last 72 hours and may no longer be available at the time of booking. We display fares for Economy Light as standard, but it is possible to change your class of service during the booking process. You can also add baggage meals and extra legroom to your trip during booking.
Flights from Chicago (ORD) to Milan (MXP) in the next 365 days
Book ahead and find our best prices in 2026 and beyond
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From | To | Fare type | Dates | Price | |
|---|---|---|---|---|---|
| Chicago (ORD) | Milan (MXP) | Round trip / Economy | Apr 06 2027 - Apr 14 2027 | From USD 645 Viewed 17 hrs ago | |
| Chicago (ORD) | Milan (MXP) | Round trip / Economy | Apr 13 2027 - Apr 28 2027 | From USD 645 Viewed 17 hrs ago | |
| Chicago (ORD) | Milan (MXP) | Round trip / Economy | Apr 20 2027 - Apr 28 2027 | From USD 645 Viewed 17 hrs ago | |
| Chicago (ORD) | Milan (MXP) | Round trip / Economy | Apr 09 2027 - Apr 21 2027 | From USD 645 Viewed 17 hrs ago | |
| Chicago (ORD) | Milan (MXP) | Round trip / Economy | Apr 06 2027 - Apr 21 2027 | From USD 645 Viewed 17 hrs ago |
*Fares displayed have been collected within the last 72hrs and may no longer be available at the time of booking. We display fares for Economy Light as standard but it is possible to change your class of service during the booking process. You can also add baggage, meals and extra legroom to your trip during booking.
Make the most of your trip
Flights from Chicago (ORD) to Milan (MXP)
Choose Icelandair to fly from Chicago (ORD) to Milan (MXP). Enjoy our refreshing travel experience, which includes hundreds of hours of movies and music in our in-seat entertainment system, USB chargers in every seat and Wi-Fi access. You'll enjoy an easy transit at our Keflavik hub and one of the shortest flying times between North America and Europe.
Looking for a flight from Chicago to the capital of Italy's Lombardy region? If you book your plane tickets to Europe with Icelandair, you can add a stopover in Iceland to your travel plans. You can make your stopover anything from 1 to 7 days, and you will have the opportunity to explore Iceland's geyser, waterfalls and caves, and to visit the charming capital of Reykjavik. Then, you can catch the plane to your final destination and take in the exquisite Duomo cathedral and explore the museums and exhibitions of the medieval Castello Sforzesco!
Flying with Icelandair: more than just a journey
Generous baggage allowances
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Entertainment for all ages
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