Flights from Chicago to Italy from USD 659
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
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 | 22/10/2026 - 30/10/2026 | From USD 724 Viewed 1 day ago | |
| Chicago (ORD) | Rome (FCO) | Round trip | Economy | 23/08/2026 - 09/09/2026 | From USD 659 Viewed 15 hours ago | |
| Chicago (ORD) | Milan (MXP) | Round trip | Economy | 15/07/2026 - 17/01/2027 | From USD 785 Viewed 1 day ago | |
| Chicago (ORD) | Milan (MXP) | Round trip | Economy | 26/06/2026 - 03/07/2026 | From USD 1,473 Viewed 1 day ago | |
| Chicago (ORD) | Florence (FLR) | Round trip | Economy | 23/08/2026 - 09/09/2026 | From USD 943 Viewed 15 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.