Travel with Air Canada from Calgary to Chicago (YYC - ORD) from CAD 167*
*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 | Jun 04, 2026 | From 8,500 pts + CAD 162 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Dec 26, 2025 | From 9,500 pts + CAD 175 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Jul 03, 2026 | From 19,600 pts + CAD 242 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Feb 17, 2026 | From 9,800 pts + CAD 151 Viewed: 1 day 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.