Flights from Chicago to Milan available from USD 853*

Our best rates from Chicago to Milan

Apr 2025
FromUSD 1,041*
Fare: Round trip/Economy
Displaying fares for April-2025
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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)
May 14 2025 - Jun 11 2025
From
USD 978
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
May 14 2025 - Jun 13 2025
From
USD 978
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
May 13 2025 - Jun 13 2025
From
USD 980
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
May 13 2025 - Jun 11 2025
From
USD 980
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
May 14 2025 - Jun 12 2025
From
USD 1,001
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
May 13 2025 - Jun 12 2025
From
USD 1,003
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
May 14 2025 - May 19 2025
From
USD 1,008
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
May 07 2025 - May 19 2025
From
USD 1,008
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		Oct 19 2025 - Nov 19 2025

From

USD 853

Viewed 2 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Oct 28 2025 - Nov 05 2025

From

USD 853

Viewed 2 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Oct 28 2025 - Nov 12 2025

From

USD 853

Viewed 2 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Oct 28 2025 - Nov 26 2025

From

USD 853

Viewed 2 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Oct 31 2025 - Nov 05 2025

From

USD 853

Viewed 2 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Oct 31 2025 - Nov 26 2025

From

USD 853

Viewed 2 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Nov 11 2025 - Nov 26 2025

From

USD 853

Viewed 2 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Nov 14 2025 - Nov 22 2025

From

USD 853

Viewed 2 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Nov 14 2025 - Dec 03 2025

From

USD 853

Viewed 2 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!

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