Travel with Air Canada from Calgary to Chicago (YYC - ORD) from CAD 168*
*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 Calgary and Chicago - our lowest fares in cash
*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 Calgary and Chicago - our lowest fares in points
From | To | Fare Type | Departure | Price |
|---|---|---|---|---|
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Jan 29, 2026 | From 8,300 pts + CAD 184 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Jan 01, 2026 | From 20,800 pts + CAD 171 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Aug 24, 2026 | From 19,200 pts + CAD 324 Viewed: 15 hours ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Aug 23, 2026 | From 23,200 pts + CAD 242 Viewed: 15 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.