Travel with Air Canada from Toronto to Chicago (YTO - ORD) from CAD 174*
*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 | Feb 13, 2026 | From 5,500 pts + CAD 120 Viewed: 10 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 30, 2025 | From 10,000 pts + CAD 159 Viewed: 10 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 26, 2025 | From 10,000 pts + CAD 184 Viewed: 1 hour ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jan 08, 2026 | From 6,000 pts + CAD 167 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 18, 2026 | From 8,700 pts + CAD 120 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 28, 2025 | From 10,000 pts + CAD 159 Viewed: 19 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jan 01, 2026 | From 10,000 pts + CAD 159 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 24, 2025 | From 10,000 pts + CAD 159 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Aug 09, 2026 | From 8,700 pts + CAD 120 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 25, 2025 | From 10,000 pts + CAD 159 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jan 09, 2026 | From 20,000 pts + CAD 317 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.