Travel with Air Canada from Toronto to Chicago (YTO - ORD) from CAD 163*
*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 | Oct 19, 2026 | From 6,000 pts + CAD 167 Viewed: 20 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 03, 2026 | From 6,000 pts + CAD 167 Viewed: 4 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 28, 2026 | From 8,600 pts + CAD 120 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 02, 2026 | From 9,100 pts + CAD 120 Viewed: 4 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Dec 17, 2025 | From 10,000 pts + CAD 159 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jan 04, 2026 | From 19,800 pts + CAD 120 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jan 01, 2026 | From 35,400 pts + CAD 500 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.