Travel with Air Canada from Toronto to Chicago (YTO - 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 Toronto 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 Toronto and Chicago - our lowest fares in points
From | To | Fare Type | Departure | Price |
|---|---|---|---|---|
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jan 10, 2026 | From 6,000 pts + CAD 167 Viewed: 22 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 27, 2025 | From 30,000 pts + CAD 440 Viewed: 20 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 21, 2025 | From 10,000 pts + CAD 159 Viewed: 4 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 29, 2025 | From 10,000 pts + CAD 159 Viewed: 35 minutes ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Feb 22, 2026 | From 17,400 pts + CAD 333 Viewed: 1 hour 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.