Flights from Chicago to Italy from USD 499
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
Naples (NAP)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 | 04/11/2026 - 10/11/2026 | From USD 499 Viewed 1 day ago | |
| Chicago (ORD) | Rome (FCO) | Round trip | Economy | 02/12/2026 - 13/12/2026 | From USD 519 Viewed 1 day ago | |
| Chicago (ORD) | Milan (MXP) | Round trip | Economy | 06/06/2026 - 13/06/2026 | From USD 1,118 Viewed 1 day ago | |
| Chicago (ORD) | Naples (NAP) | Round trip | Economy | 28/08/2026 - 02/09/2026 | From USD 843 Viewed 1 day ago | |
| Chicago (ORD) | Venice (VCE) | Round trip | Economy | 30/09/2026 - 07/10/2026 | From USD 871 Viewed 2 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.