Flights from Chicago to Milan available from USD 395*

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Our best rates from Chicago to Milan

Jul 2025
FromUSD 709*
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)
    Sep 26 2025 - Oct 26 2025
    From
    USD 402
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Sep 26 2025 - Oct 23 2025
    From
    USD 403
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Sep 26 2025 - Oct 13 2025
    From
    USD 403
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Sep 26 2025 - Oct 02 2025
    From
    USD 403
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Sep 26 2025 - Oct 06 2025
    From
    USD 403
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Sep 12 2025 - Oct 02 2025
    From
    USD 405
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Sep 12 2025 - Oct 06 2025
    From
    USD 405
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Sep 12 2025 - Oct 13 2025
    From
    USD 405
    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.

     

    Blue image with a map of Iceland and text that reads: Include a little more of Iceland in your journey. Add a Stopover

    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    		Mar 31 2026 - Apr 22 2026

    From

    USD 798

    Viewed 4 hrs ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Mar 31 2026 - Apr 29 2026

    From

    USD 798

    Viewed 4 hrs ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Mar 27 2026 - Apr 22 2026

    From

    USD 815

    Viewed 1 day ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 03 2026 - Apr 22 2026

    From

    USD 815

    Viewed 1 day ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 03 2026 - Apr 29 2026

    From

    USD 815

    Viewed 1 day ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Mar 29 2026 - Apr 29 2026

    From

    USD 882

    Viewed 1 day ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 05 2026 - Apr 22 2026

    From

    USD 882

    Viewed 4 hrs ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Mar 30 2026 - Apr 29 2026

    From

    USD 882

    Viewed 4 hrs ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Apr 01 2026 - Apr 22 2026

    From

    USD 882

    Viewed 4 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.

    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!