Cheap flights to Italy from Chicago

Round trips from Chicago from $409. Cheapest dates, deal ratings and where to book.

• Rome: $409, 2027-02-16 to 2027-02-19
• Orio al Serio (BG): $734, 2027-02-14 to 2027-02-19
• Catania: $1478, 2026-12-21 to 2027-01-03

Nearby

• Vatican City
• San Marino
• Croatia
• Monaco
• Slovenia
• Bosnia and Herzegovina
• Liechtenstein
• Montenegro