Flights from Chicago to Italy from USD 358
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
Venice (VCE)*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 | 24/10/2025 - 05/11/2025 | From USD 358 Viewed 8 hours ago | |
| Chicago (ORD) | Rome (FCO) | Round-trip | Economy | 29/10/2025 - 05/11/2025 | From USD 358 Viewed 3 hours ago | |
| Chicago (ORD) | Milan (MXP) | Round-trip | Economy | 09/10/2025 - 16/10/2025 | From USD 859 Viewed 23 hours ago | |
| Chicago (ORD) | Venice (VCE) | Round-trip | Economy | 29/03/2026 - 07/04/2026 | From USD 602 Viewed 4 hours ago | |
| Chicago (ORD) | Venice (VCE) | Round-trip | Economy | 29/09/2025 - 21/10/2025 | From USD 821 Viewed 23 hours ago | |
| Chicago (ORD) | Naples (NAP) | Round-trip | Economy | 05/06/2026 - 13/06/2026 | From USD 961 Viewed 1 day ago | |
| Chicago (ORD) | Florence (FLR) | Round-trip | Economy | 17/06/2026 - 01/07/2026 | From USD 1,174 Viewed 1 day 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.