Flights from Chicago to Italy from $ 692*
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1 Passenger, Economy
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today
today
Find United's best fares from Chicago to Italy
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$
Chicago (ORD)to
Rome (FCO)02/01/27 - 02/10/27from$ 695Viewed: 15 hours agoRoundtripEconomy
Chicago (ORD)to
Milan (MXP)05/13/26 - 05/27/26from$ 1,276Viewed: 3 hours agoRoundtripEconomy
Chicago (ORD)to
Venice (VCE)04/21/26 - 05/05/26from$ 834Viewed: 3 hours agoRoundtripEconomy
Chicago (ORD)to
Florence (FLR)02/11/27 - 02/18/27from$ 804Viewed: 23 hours agoRoundtripEconomy
Chicago (ORD)to
Naples (NAP)04/15/26 - 04/22/26from$ 705Viewed: 1 hour agoRoundtripEconomy
Chicago (ORD)to
Palermo (PMO)04/16/26 - 04/21/26from$ 751Viewed: 8 minutes agoRoundtripEconomy
Chicago (ORD)to
Bologna (BLQ)04/22/26 - 04/29/26from$ 828Viewed: 19 hours agoRoundtripEconomy
*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
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flight_land
$
Chicago (ORD)to
Rome (FCO)
08/05/26 - 08/25/26
Roundtrip
Business
from
$ 3,667
Viewed: 22 hours ago
Chicago (ORD)to
Milan (MXP)
07/10/26 - 07/30/26
Roundtrip
Business
from
$ 5,824
Viewed: 19 minutes ago
Chicago (ORD)to
Florence (FLR)
04/05/26 - 04/10/26
Roundtrip
Business
from
$ 3,563
Viewed: 20 hours ago
Chicago (ORD)to
Venice (VCE)
08/25/26 - 09/15/26
Roundtrip
Business
from
$ 5,108
Viewed: 1 day ago
Chicago (ORD)to
Naples (NAP)
03/30/26 - 04/06/26
Roundtrip
Business
from
$ 4,061
Viewed: 19 hours ago
Chicago (ORD)to
Palermo (PMO)
08/12/26 - 08/21/26
Roundtrip
Business
from
$ 6,124
Viewed: 1 hour ago
Chicago (ORD)to
Bologna (BLQ)
05/12/26 - 05/18/26
Roundtrip
Business
from
$ 3,895
Viewed: 12 hours 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.