Flights from Chicago to Milan available from USD 1,048*

Promo code

Our best rates from Chicago to Milan

Mar 2027
FromUSD 1,148*
Fare: Round trip/Economy
Apr 2027
FromUSD 1,048*
Fare: Round trip/Economy
May 2027
FromUSD 1,091*
Fare: Round trip/Economy
Displaying fares for October-2026
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  • ORD–MXP, Mar 19 2027 – Mar 24 2027: From USD 1,205
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  • ORD–MXP, Mar 23 2027 – Apr 03 2027: From USD 1,205
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  • ORD–MXP, Mar 26 2027 – Apr 14 2027: From USD 1,198
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  • ORD–MXP, Mar 30 2027 – Apr 14 2027: From USD 1,148
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    • *Fares displayed have been collected within the last 72hrs and may no longer be available at the time of booking

    Fly in the next 3 months: flights from Chicago to Milan (MXP)

    Icelandair airfare from Chicago to Milan

    USD
    *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

    USD
    Flights from Chicago (ORD) to Milan (MXP) in the next 365 days
    From
    To
    Fare type
    Dates
    Price
    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 06 2027 - Apr 14 2027

    From

    USD 1,048

    Viewed 2 days ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 13 2027 - Apr 28 2027

    From

    USD 1,048

    Viewed 2 days ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 20 2027 - Apr 28 2027

    From

    USD 1,048

    Viewed 2 days 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.

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    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