Flights from Chicago to Italy from USD 628
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1 Passenger, Economy
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Best Flight Deals from Chicago to Italy
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USD
Chicago (ORD)to
Rome (FCO)11/11/2026 - 03/12/2026
From
USD 628
Viewed 1 day ago
Round trip
Economy
Chicago (ORD)to
Rome (FCO)01/10/2026 - 09/10/2026
From
USD 918
Viewed 15 hours ago
Round trip
Economy
Chicago (ORD)to
Milan (MXP)22/11/2026 - 30/11/2026
From
USD 1,099
Viewed 6 hours ago
Round trip
Economy
Chicago (ORD)to
Milan (MXP)18/12/2026 - 03/01/2027
From
USD 1,514
Viewed 1 day 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
flight_takeoff
flight_land
USD
Chicago (ORD)to
Rome (FCO)
11/11/2026 - 03/12/2026
Round trip
Business
From
USD 3,271
Viewed 1 day ago
Chicago (ORD)to
Rome (FCO)
01/10/2026 - 09/10/2026
Round trip
Business
From
USD 5,831
Viewed 15 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 | 11/11/2026 - 03/12/2026 | From USD 628 Viewed 1 day ago | |
| Chicago (ORD) | Rome (FCO) | Round trip | Economy | 14/03/2027 - 23/03/2027 | From USD 628 Viewed 1 day ago | |
| Chicago (ORD) | Milan (MXP) | Round trip | Economy | 26/03/2027 - 03/04/2027 | From USD 804 Viewed 1 day ago | |
| Chicago (ORD) | Milan (MXP) | Round trip | Economy | 02/07/2027 - 11/07/2027 | From USD 909 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.