Flights from Chicago to Italy available from USD 550*

Promo code

Deals on flights in next three months

USD

Chicago (ORD)to

Rome (FCO)
Jul 28 2025 - Aug 26 2025
From
USD 576
Viewed 15 hrs ago
Round trip
/
Economy

Chicago (ORD)to

Rome (FCO)
Jul 27 2025 - Aug 26 2025
From
USD 577
Viewed 15 hrs ago
Round trip
/
Economy

Chicago (ORD)to

Rome (FCO)
Jul 22 2025 - Aug 18 2025
From
USD 609
Viewed 15 hrs ago
Round trip
/
Economy

Chicago (ORD)to

Rome (FCO)
Jul 21 2025 - Aug 18 2025
From
USD 609
Viewed 15 hrs ago
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
Jul 27 2025 - Aug 22 2025
From
USD 867
Viewed 2 days ago
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
Jul 28 2025 - Aug 20 2025
From
USD 867
Viewed 2 days ago
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
Jul 23 2025 - Aug 22 2025
From
USD 867
Viewed 2 days ago
Round trip
/
Economy

Chicago (ORD)to

Milan (MXP)
Jul 22 2025 - Aug 20 2025
From
USD 867
Viewed 2 days ago
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 Italy with Icelandair

USD
Plan ahead for your trip from Chicago to Italy with Icelandair
From
To
Fare type
Dates
Price
Chicago (ORD)Rome (FCO)Round trip
/
Economy		Jan 17 2026 - Jan 24 2026

From

USD 550

Viewed 1 day ago

Chicago (ORD)Milan (MXP)Round trip
/
Economy		Oct 25 2025 - Nov 12 2025

From

USD 854

Viewed 2 days 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.

 

Our most popular connections