Flights from Chicago to Milan available from USD 395*

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Our best rates from Chicago to Milan

*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)
Jan 13 2026 - Feb 03 2026
From
USD 857
Round trip
Economy

Chicago (ORD)to

Milan (MXP)
Jan 13 2026 - Feb 05 2026
From
USD 857
Round trip
Economy

Chicago (ORD)to

Milan (MXP)
Jan 13 2026 - Feb 06 2026
From
USD 857
Round trip
Economy

Chicago (ORD)to

Milan (MXP)
Jan 26 2026 - Feb 03 2026
From
USD 857
Round trip
Economy

Chicago (ORD)to

Milan (MXP)
Jan 26 2026 - Feb 06 2026
From
USD 857
Round trip
Economy

Chicago (ORD)to

Milan (MXP)
Jan 13 2026 - Jan 21 2026
From
USD 857
Round trip
Economy

Chicago (ORD)to

Milan (MXP)
Jan 13 2026 - Jan 23 2026
From
USD 857
Round trip
Economy

Chicago (ORD)to

Milan (MXP)
Jan 13 2026 - Jan 28 2026
From
USD 857
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		Aug 31 2026 - Oct 01 2026

From

USD 694

Viewed 11 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Sep 01 2026 - Oct 01 2026

From

USD 695

Viewed 11 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Aug 26 2026 - Sep 22 2026

From

USD 701

Viewed 11 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Aug 31 2026 - Sep 17 2026

From

USD 701

Viewed 11 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Aug 31 2026 - Sep 24 2026

From

USD 701

Viewed 11 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Aug 23 2026 - Sep 17 2026

From

USD 701

Viewed 11 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Aug 23 2026 - Sep 22 2026

From

USD 701

Viewed 11 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Aug 31 2026 - Sep 22 2026

From

USD 701

Viewed 11 hrs ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Aug 31 2026 - Sep 29 2026

From

USD 701

Viewed 11 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!