Flights from Chicago to Italy from USD 609
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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)11/09/2026 - 19/09/2026
From
USD 609
Viewed 5 hours ago
Round trip
Economy
Chicago (ORD)to
Milan (MXP)01/10/2026 - 09/10/2026
From
USD 888
Viewed 1 day ago
Round trip
Economy
Chicago (ORD)to
Florence (FLR)03/10/2026 - 13/10/2026
From
USD 1,015
Viewed 8 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)
11/09/2026 - 19/09/2026
Round trip
Business
From
USD 5,830
Viewed 5 hours ago
Chicago (ORD)to
Milan (MXP)
01/10/2026 - 09/10/2026
Round trip
Business
From
USD 6,261
Viewed 1 day ago
Chicago (ORD)to
Florence (FLR)
03/10/2026 - 13/10/2026
Round trip
Business
From
USD 6,322
Viewed 8 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 | 11/09/2026 - 19/09/2026 | From USD 609 Viewed 5 hours ago | |
| Chicago (ORD) | Rome (FCO) | Round trip | Economy | 19/02/2027 - 28/02/2027 | From USD 667 Viewed 1 day ago | |
| Chicago (ORD) | Milan (MXP) | Round trip | Economy | 01/10/2026 - 09/10/2026 | From USD 888 Viewed 1 day ago | |
| Chicago (ORD) | Florence (FLR) | Round trip | Economy | 03/10/2026 - 13/10/2026 | From USD 1,015 Viewed 8 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.