Cheap flights to Italy from Chicago

Round trips from Chicago from $439. Cheapest dates, deal ratings and where to book.

• Rome: $439, 2027-02-15 to 2027-02-23
• Orio al Serio (BG): $734, 2027-02-14 to 2027-02-19
• Venezia (VE): $738, 2026-11-30 to 2026-12-06
• Catania: $1409, 2026-12-21 to 2027-01-04

Nearby

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