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 | Dec 22, 2025 | From 10,000 pts + CAD 159 Viewed: 2 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 23, 2025 | From 10,000 pts + CAD 159 Viewed: 2 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 20, 2025 | From 10,000 pts + CAD 167 Viewed: 17 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 21, 2025 | From 10,000 pts + CAD 167 Viewed: 17 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jan 10, 2026 | From 12,000 pts + CAD 333 Viewed: 17 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 08, 2026 | From 17,800 pts + CAD 239 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 29, 2026 | From 9,200 pts + CAD 183 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 18, 2025 | From 10,000 pts + CAD 167 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 19, 2025 | From 10,000 pts + CAD 159 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 31, 2025 | From 10,000 pts + CAD 167 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.