Flights from Chicago to Italy from $ 442*

Promotion Code

Changed bag rules and optional services         Cruise Packages

Find United's best fares from Chicago to Italy

$
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  • Chicago (ORD)to

    Naples (NAP)
    01/28/26 - 02/04/26
    from
    $ 468
    Viewed: 4 hours ago
    Roundtrip
    Economy

    Chicago (ORD)to

    Palermo (PMO)
    03/02/26 - 03/09/26
    from
    $ 823
    Viewed: 21 hours ago
    Roundtrip
    Economy

    Chicago (ORD)to

    Bologna (BLQ)
    01/27/26 - 02/10/26
    from
    $ 668
    Viewed: 21 hours ago
    Roundtrip
    Economy

*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.

Business class flights from Chicago to Italy

$

Chicago (ORD)to

Rome (FCO)
12/08/25 - 12/15/25

Roundtrip

Business

from
$ 3,313
Viewed: 18 hours ago

Chicago (ORD)to

Milan (MXP)
01/02/26 - 01/14/26

Roundtrip

Business

from
$ 2,942
Viewed: 1 day ago

Chicago (ORD)to

Florence (FLR)
08/18/26 - 08/26/26

Roundtrip

Business

from
$ 2,886
Viewed: 12 hours ago

Chicago (ORD)to

Venice (VCE)
10/20/26 - 10/30/26

Roundtrip

Business

from
$ 4,664
Viewed: 12 hours ago

Chicago (ORD)to

Naples (NAP)
03/30/26 - 04/07/26

Roundtrip

Business

from
$ 4,433
Viewed: 4 hours ago

Chicago (ORD)to

Palermo (PMO)
09/07/26 - 09/28/26

Roundtrip

Business

from
$ 5,388
Viewed: 8 hours ago

Chicago (ORD)to

Bologna (BLQ)
04/02/26 - 04/11/26

Roundtrip

Business

from
$ 3,409
Viewed: 1 day ago

*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.