Compare Chicago to Italy flight deals starting at $444

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Find flights from Chicago (ORD) to Italy

Chicago (ORD) to Rome (FCO)

Depart Mon 26 Nov 2018,
Return Tue 11 Dec 2018
from$ 483*Viewed: 2 hours ago

Chicago (ORD) to Milan (MIL)

Depart Mon 19 Nov 2018,
Return Tue 4 Dec 2018
from$ 444*Viewed: 2 hours ago

Chicago (ORD) to Venice (VCE)

Depart Tue 15 Jan 2019,
Return Wed 30 Jan 2019
from$ 481*Viewed: 2 hours ago

Chicago (ORD) to Naples (NAP)

Depart Wed 16 Jan 2019,
Return Thu 31 Jan 2019
from$ 503*Viewed: 1 hour ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. 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.
Staggered homes on the cliffs of the coast in Italy lined by bight fuchsia flowers

Plan ahead for flights from Chicago to Italy

from
to
Type
Dates
Price*
Chicago (ORD)
to Milan (MIL)
Roundtrip
Depart Mon 19 Nov 2018
Return Tue 4 Dec 2018
from$ 444*Viewed: 2 hours ago
Chicago (ORD)
to Venice (VCE)
Roundtrip
Depart Tue 15 Jan 2019
Return Wed 30 Jan 2019
from$ 481*Viewed: 2 hours ago
Chicago (ORD)
to Rome (FCO)
Roundtrip
Depart Mon 26 Nov 2018
Return Tue 11 Dec 2018
from$ 483*Viewed: 2 hours ago
Chicago (ORD)
to Naples (NAP)
Roundtrip
Depart Wed 16 Jan 2019
Return Thu 31 Jan 2019
from$ 503*Viewed: 1 hour ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. 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.