Flights from Chicago to Italy from USD 603
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1 Passenger, Economy
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Promo Code
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Best Flight Deals from Chicago to Italy
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USD
Chicago (ORD)to
Rome (FCO)06/11/2026 - 14/11/2026
From
USD 603
Viewed 1 hour ago
Round trip
Economy
Chicago (ORD)to
Rome (FCO)20/01/2027 - 31/01/2027
From
USD 609
Viewed 1 day ago
Round trip
Economy
Chicago (ORD)to
Milan (MXP)16/09/2026 - 27/09/2026
From
USD 884
Viewed 14 hours ago
Round trip
Economy
Chicago (ORD)to
Bologna (BLQ)09/08/2026 - 28/08/2026
From
USD 760
Viewed 13 hours ago
Round trip
Economy
Chicago (ORD)to
Bologna (BLQ)07/10/2026 - 12/10/2026
From
USD 975
Viewed 1 day ago
Round trip
Economy
Chicago (ORD)to
Florence (FLR)03/10/2026 - 13/10/2026
From
USD 1,015
Viewed 1 day ago
Round trip
Economy
Chicago (ORD)to
Florence (FLR)16/10/2026 - 28/10/2026
From
USD 1,131
Viewed 3 hours ago
Round trip
Economy
*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
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USD
Chicago (ORD)to
Rome (FCO)
06/08/2026 - 13/08/2026
Round trip
Business
From
USD 4,252
Viewed 9 hours ago
Chicago (ORD)to
Rome (FCO)
12/09/2026 - 21/09/2026
Round trip
Business
From
USD 4,630
Viewed 8 hours ago
Chicago (ORD)to
Milan (MXP)
16/09/2026 - 27/09/2026
Round trip
Business
From
USD 6,267
Viewed 14 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.
Best Flight Deals from Chicago to Italy
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USD
From | To | Fare Type | Dates | Price | |
|---|---|---|---|---|---|
| Chicago (ORD) | Rome (FCO) | Round trip | Economy | 06/11/2026 - 14/11/2026 | From USD 603 Viewed 1 hour ago | |
| Chicago (ORD) | Rome (FCO) | Round trip | Economy | 20/01/2027 - 31/01/2027 | From USD 609 Viewed 1 day ago | |
| Chicago (ORD) | Milan (MXP) | Round trip | Economy | 16/09/2026 - 27/09/2026 | From USD 884 Viewed 14 hours ago | |
| Chicago (ORD) | Bologna (BLQ) | Round trip | Economy | 07/10/2026 - 12/10/2026 | From USD 975 Viewed 1 day ago | |
| Chicago (ORD) | Florence (FLR) | Round trip | Economy | 03/10/2026 - 13/10/2026 | From USD 1,015 Viewed 1 day ago | |
| Chicago (ORD) | Florence (FLR) | Round trip | Economy | 16/10/2026 - 28/10/2026 | From USD 1,131 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.