Travel with Air Canada from Toronto to Chicago (YTO - ORD) from CAD 173*
*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 18, 2026 | From 6,000 pts + CAD 166 Viewed: 4 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jan 19, 2026 | From 8,000 pts + CAD 166 Viewed: 4 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jan 12, 2026 | From 9,200 pts + CAD 163 Viewed: 7 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 12, 2026 | From 18,600 pts + CAD 358 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Feb 13, 2026 | From 18,900 pts + CAD 358 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 13, 2026 | From 22,200 pts + CAD 547 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Feb 01, 2026 | From 6,000 pts + CAD 166 Viewed: 22 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 09, 2026 | From 6,200 pts + CAD 120 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jan 10, 2026 | From 12,000 pts + CAD 332 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jan 09, 2026 | From 14,800 pts + CAD 364 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.