Flights from Chicago to Italy from USD 337

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Best Flight Deals from Chicago to Italy

USD
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Chicago (ORD)to

Rome (FCO)
23/08/2025 - 05/09/2025
From
USD 337
Viewed 1 day ago
Round-trip
Economy

Chicago (ORD)to

Rome (FCO)
09/10/2025 - 21/10/2025
From
USD 337
Viewed 1 day ago
Round-trip
Economy

Chicago (ORD)to

Milan (MXP)
15/08/2025 - 22/08/2025
From
USD 442
Viewed 1 day ago
Round-trip
Economy

Chicago (ORD)to

Milan (MXP)
15/08/2025 - 23/08/2025
From
USD 442
Viewed 1 day ago
Round-trip
Economy

Chicago (ORD)to

Venice (VCE)
14/08/2025 - 23/08/2025
From
USD 522
Viewed 14 hours ago
Round-trip
Economy

Chicago (ORD)to

Venice (VCE)
02/09/2025 - 08/09/2025
From
USD 1,074
Viewed 11 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

USD

Chicago (ORD)to

Rome (FCO)
24/08/2025 - 07/09/2025

Round-trip

Business

From
USD 2,749
Viewed 7 hours ago

Chicago (ORD)to

Rome (FCO)
24/08/2025 - 05/09/2025

Round-trip

Business

From
USD 2,749
Viewed 1 day ago

Chicago (ORD)to

Milan (MXP)
15/08/2025 - 22/08/2025

Round-trip

Business

From
USD 3,528
Viewed 1 day ago

Chicago (ORD)to

Milan (MXP)
15/08/2025 - 23/08/2025

Round-trip

Business

From
USD 3,528
Viewed 1 day ago

Chicago (ORD)to

Venice (VCE)
14/08/2025 - 23/08/2025

Round-trip

Business

From
USD 3,411
Viewed 14 hours ago

Chicago (ORD)to

Venice (VCE)
16/07/2025 - 24/07/2025

Round-trip

Business

From
USD 5,103
Viewed 18 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

USD
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Best Flight Deals from Chicago to Italy
From
To
Fare Type
Dates
Price
Chicago (ORD)Rome (FCO)Round-trip
|
Economy
23/08/2025 - 05/09/2025

From

USD 337

Viewed 1 day ago

Chicago (ORD)Rome (FCO)Round-trip
|
Economy
11/03/2026 - 20/03/2026

From

USD 337

Viewed 1 day ago

Chicago (ORD)Milan (MXP)Round-trip
|
Economy
15/08/2025 - 22/08/2025

From

USD 442

Viewed 1 day ago

Chicago (ORD)Milan (MXP)Round-trip
|
Economy
15/08/2025 - 23/08/2025

From

USD 442

Viewed 1 day ago

Chicago (ORD)Venice (VCE)Round-trip
|
Economy
06/02/2026 - 14/02/2026

From

USD 522

Viewed 13 hours ago

Chicago (ORD)Venice (VCE)Round-trip
|
Economy
14/08/2025 - 23/08/2025

From

USD 522

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.