Flights from Chicago to Italy from USD 395
Best Flight Deals from Chicago to Italy
Chicago (ORD)to
Rome (FCO)Chicago (ORD)to
Rome (FCO)Chicago (ORD)to
Milan (MXP)Chicago (ORD)to
Milan (MXP)Chicago (ORD)to
Florence (FLR)*The fares shown have been updated in the last 48 hours and may no longer be available at the time of booking. Additional fees and charges may apply for optional products and services.
Business Flights Deals
Chicago (ORD)to
Round-trip
Business
Chicago (ORD)to
Round-trip
Business
Chicago (ORD)to
Round-trip
Business
*The fares shown have been updated in the last 48 hours and may no longer be available at the time of booking. Additional fees and charges may apply for optional products and services.
Best Flight Deals from Chicago to Italy
From | To | Fare Type | Dates | Price | |
|---|---|---|---|---|---|
| Chicago (ORD) | Rome (FCO) | Round-trip | Economy | 23/08/2025 - 30/08/2025 | From USD 395 Viewed 12 hours ago | |
| Chicago (ORD) | Rome (FCO) | Round-trip | Economy | 09/10/2025 - 16/10/2025 | From USD 395 Viewed 12 hours ago | |
| Chicago (ORD) | Milan (MXP) | Round-trip | Economy | 28/08/2025 - 07/09/2025 | From USD 500 Viewed 15 hours ago | |
| Chicago (ORD) | Milan (MXP) | Round-trip | Economy | 07/12/2025 - 17/12/2025 | From USD 530 Viewed 1 day ago | |
| Chicago (ORD) | Florence (FLR) | Round-trip | Economy | 25/09/2025 - 03/10/2025 | From USD 549 Viewed 12 hours ago |
*The fares shown have been updated in the last 48 hours and may no longer be available at the time of booking. Additional fees and charges may apply for optional products and services.