Flights from Chicago to Italy from USD 430
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)Chicago (ORD)to
Florence (FLR)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
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 | 22/04/2026 - 01/05/2026 | From USD 498 Viewed 1 day ago | |
| Chicago (ORD) | Rome (FCO) | Round trip | Economy | 09/10/2026 - 23/10/2026 | From USD 575 Viewed 1 day ago | |
| Chicago (ORD) | Milan (MXP) | Round trip | Economy | 29/05/2026 - 12/06/2026 | From USD 790 Viewed 1 day ago | |
| Chicago (ORD) | Milan (MXP) | Round trip | Economy | 04/03/2026 - 10/03/2026 | From USD 430 Viewed 27 minutes ago | |
| Chicago (ORD) | Naples (NAP) | Round trip | Economy | 18/07/2026 - 03/08/2026 | From USD 1,558 Viewed 4 hours ago | |
| Chicago (ORD) | Florence (FLR) | Round trip | Economy | 22/05/2026 - 01/06/2026 | From USD 1,311 Viewed 9 hours ago | |
| Chicago (ORD) | Florence (FLR) | Round trip | Economy | 04/04/2026 - 26/04/2026 | From USD 1,176 Viewed 1 day ago | |
| Chicago (ORD) | Bologna (BLQ) | Round trip | Economy | 22/07/2026 - 01/08/2026 | From USD 771 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.