Flights from Chicago to Italy from $ 520*

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)
    02/25/26 - 03/04/26
    from
    $ 549
    Viewed: 3 hours ago
    Roundtrip
    Economy

    Chicago (ORD)to

    Palermo (PMO)
    03/02/26 - 03/16/26
    from
    $ 859
    Viewed: 20 hours ago
    Roundtrip
    Economy

    Chicago (ORD)to

    Bologna (BLQ)
    02/10/26 - 02/24/26
    from
    $ 821
    Viewed: 19 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)
01/13/26 - 01/20/26

Roundtrip

Business

from
$ 3,000
Viewed: 1 day ago

Chicago (ORD)to

Milan (MXP)
09/01/26 - 10/01/26

Roundtrip

Business

from
$ 6,065
Viewed: 23 hours ago

Chicago (ORD)to

Florence (FLR)
04/07/26 - 04/16/26

Roundtrip

Business

from
$ 5,043
Viewed: 20 hours ago

Chicago (ORD)to

Venice (VCE)
07/26/26 - 08/04/26

Roundtrip

Business

from
$ 5,524
Viewed: 22 hours ago

Chicago (ORD)to

Naples (NAP)
04/15/26 - 04/22/26

Roundtrip

Business

from
$ 5,425
Viewed: 16 hours ago

Chicago (ORD)to

Bologna (BLQ)
03/04/26 - 03/19/26

Roundtrip

Business

from
$ 5,039
Viewed: 19 hours ago

Chicago (ORD)to

Palermo (PMO)
04/01/26 - 04/24/26

Roundtrip

Business

from
$ 4,935
Viewed: 54 minutes 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.