Flights from Chicago to Milan available from USD 550*

Our best rates from Chicago to Milan

Jan 2025
FromUSD 550*
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)
Feb 26 2025 - Mar 09 2025
From
USD 550*
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
Feb 25 2025 - Mar 28 2025
From
USD 550*
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
Mar 18 2025 - Mar 20 2025
From
USD 550*
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
Jan 24 2025 - Feb 21 2025
From
USD 550*
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
Jan 12 2025 - Jan 16 2025
From
USD 550*
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
Feb 05 2025 - Feb 09 2025
From
USD 550*
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
Feb 05 2025 - Feb 23 2025
From
USD 550*
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
Feb 10 2025 - Feb 27 2025
From
USD 550*
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
FromChicago (ORD)ToMilan (MXP)Round trip
/
Economy		Sep 24 2025 - Oct 17 2025

From

USD 552*

Viewed 1 day ago

FromChicago (ORD)ToMilan (MXP)Round trip
/
Economy		Sep 19 2025 - Oct 04 2025

From

USD 552*

Viewed 1 day ago

FromChicago (ORD)ToMilan (MXP)Round trip
/
Economy		Oct 02 2025 - Oct 26 2025

From

USD 552*

Viewed 1 day ago

FromChicago (ORD)ToMilan (MXP)Round trip
/
Economy		Oct 13 2025 - Oct 23 2025

From

USD 552*

Viewed 1 day ago

FromChicago (ORD)ToMilan (MXP)Round trip
/
Economy		Oct 01 2025 - Oct 21 2025

From

USD 552*

Viewed 1 day ago

FromChicago (ORD)ToMilan (MXP)Round trip
/
Economy		Sep 30 2025 - Oct 17 2025

From

USD 552*

Viewed 1 day ago

FromChicago (ORD)ToMilan (MXP)Round trip
/
Economy		Oct 08 2025 - Nov 05 2025

From

USD 552*

Viewed 1 day ago

FromChicago (ORD)ToMilan (MXP)Round trip
/
Economy		Oct 11 2025 - Oct 18 2025

From

USD 552*

Viewed 1 day ago

FromChicago (ORD)ToMilan (MXP)Round trip
/
Economy		Oct 15 2025 - Nov 12 2025

From

USD 577*

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!

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