Flights from Chicago to Italy from USD 449
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
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
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 | 27/09/2025 - 21/10/2025 | From USD 449 Viewed 21 hours ago | |
| Chicago (ORD) | Rome (FCO) | Round-trip | Economy | 14/01/2026 - 23/01/2026 | From USD 449 Viewed 1 hour ago | |
| Chicago (ORD) | Milan (MXP) | Round-trip | Economy | 28/07/2025 - 22/08/2025 | From USD 609 Viewed 1 day ago | |
| Chicago (ORD) | Milan (MXP) | Round-trip | Economy | 12/11/2025 - 13/12/2025 | From USD 632 Viewed 1 day ago | |
| Chicago (ORD) | Venice (VCE) | Round-trip | Economy | 14/06/2025 - 26/07/2025 | From USD 1,272 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.