Explore Air Canada flights from Chicago to Italy from CAD 1,658*
*Fares displayed have been collected within the last 48 hours and may no longer be available at the time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.
Flights between Chicago and Italy - our lowest fares in cash
Chicago (ORD)to
Milan (MXP)*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.
Flights between Chicago and Italy - our lowest fares in points
From | To | Fare Type | Departure | Price |
|---|---|---|---|---|
| Chicago (ORD) | Rome (FCO) | Round-trip / Economy | May 10, 2026 - May 19, 2026 | From 80,000 pts + CAD 240 Viewed: 1 day ago |
| Chicago (ORD) | Naples (NAP) | Round-trip / Economy | Jun 21, 2026 - Jul 09, 2026 | From 884,400 pts + CAD 1,418 Viewed: 1 day ago |
| Chicago (ORD) | Catania (CTA) | Round-trip / Economy | Aug 14, 2026 - Aug 18, 2026 | From 80,000 pts + CAD 214 Viewed: 14 hours ago |
*Points displayed do not reflect preferred pricing for Aeroplan Elite Status Members and/or Aeroplan Credit Cardholders. Prices have been collected within the past 48 hrs and may no longer be available at time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.