Travel with Air Canada from Calgary to Chicago (YYC - ORD) from CAD 180*
*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 | Aug 08, 2026 | From 12,300 pts + CAD 180 Viewed: 17 hours ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Sep 08, 2026 | From 10,700 pts + CAD 181 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Sep 09, 2026 | From 10,800 pts + CAD 129 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Mar 02, 2026 | From 11,600 pts + CAD 219 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Mar 03, 2026 | From 11,600 pts + CAD 123 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Jun 01, 2026 | From 15,000 pts + CAD 157 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.