Flights from Chicago to Milan available from USD 649*

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Our best rates from Chicago to Milan

Jul 2026
FromUSD 806*
Fare: Round trip/Economy
Aug 2026
FromUSD 769*
Fare: Round trip/Economy
Sep 2026
FromUSD 707*
Fare: Round trip/Economy
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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 three months: flights from Chicago to Milan

    USD

    Chicago (ORD)to

    Milan (MXP)
    Oct 02 2026 - Oct 11 2026
    From
    USD 699
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Oct 05 2026 - Oct 18 2026
    From
    USD 699
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Oct 03 2026 - Oct 11 2026
    From
    USD 699
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Oct 07 2026 - Oct 11 2026
    From
    USD 699
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Oct 05 2026 - Oct 11 2026
    From
    USD 699
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Oct 02 2026 - Oct 18 2026
    From
    USD 699
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Oct 03 2026 - Oct 18 2026
    From
    USD 699
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Oct 10 2026 - Oct 18 2026
    From
    USD 699
    Round trip
    Economy
    *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.
     

    Plan ahead for your trip from Chicago to Milan with Icelandair

    USD
    Plan ahead for your trip from Chicago to Milan with Icelandair
    From
    To
    Fare type
    Dates
    Price
    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 06 2027 - Apr 14 2027

    From

    USD 649

    Viewed 21 hrs ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 06 2027 - Apr 21 2027

    From

    USD 649

    Viewed 21 hrs ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 06 2027 - Apr 28 2027

    From

    USD 649

    Viewed 21 hrs ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 06 2027 - Apr 24 2027

    From

    USD 651

    Viewed 21 hrs ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 06 2027 - Apr 17 2027

    From

    USD 651

    Viewed 21 hrs ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 13 2027 - Apr 21 2027

    From

    USD 649

    Viewed 1 day ago

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

    From

    USD 649

    Viewed 1 day ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 13 2027 - Apr 17 2027

    From

    USD 651

    Viewed 1 day ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 13 2027 - Apr 24 2027

    From

    USD 651

    Viewed 1 day 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.

    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!