Flights from Chicago to Italy from USD 429
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
Bologna (BLQ)Chicago (ORD)to
Florence (FLR)Chicago (ORD)to
Florence (FLR)Chicago (ORD)to
Venice (VCE)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
*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 | 11/04/2026 - 21/04/2026 | From USD 429 Viewed 1 day ago | |
| Chicago (ORD) | Rome (FCO) | Round trip | Economy | 06/05/2026 - 16/05/2026 | From USD 429 Viewed 1 day ago | |
| Chicago (ORD) | Milan (MXP) | Round trip | Economy | 06/05/2026 - 20/05/2026 | From USD 429 Viewed 1 day ago | |
| Chicago (ORD) | Milan (MXP) | Round trip | Economy | 10/05/2026 - 17/05/2026 | From USD 656 Viewed 18 hours ago | |
| Chicago (ORD) | Bologna (BLQ) | Round trip | Economy | 08/04/2026 - 30/04/2026 | From USD 516 Viewed 10 hours ago | |
| Chicago (ORD) | Florence (FLR) | Round trip | Economy | 03/05/2026 - 15/05/2026 | From USD 440 Viewed 1 day ago | |
| Chicago (ORD) | Florence (FLR) | Round trip | Economy | 19/04/2026 - 28/04/2026 | From USD 616 Viewed 1 day ago | |
| Chicago (ORD) | Venice (VCE) | Round trip | Economy | 01/03/2026 - 10/03/2026 | From USD 516 Viewed 3 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.