Travel with Air Canada from Toronto to Chicago (YTO - ORD) from CAD 201*
*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 | Aug 01, 2026 | From 6,000 pts + CAD 171 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Aug 15, 2026 | From 6,000 pts + CAD 171 Viewed: 15 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 15, 2026 | From 6,000 pts + CAD 171 Viewed: 15 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 30, 2026 | From 9,200 pts + CAD 164 Viewed: 6 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 20, 2026 | From 10,000 pts + CAD 164 Viewed: 19 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 21, 2026 | From 10,000 pts + CAD 164 Viewed: 11 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 24, 2026 | From 20,000 pts + CAD 327 Viewed: 1 day ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Jun 21, 2026 | From 9,200 pts + CAD 213 Viewed: 8 hours ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Aug 15, 2026 | From 18,400 pts + CAD 224 Viewed: 18 hours 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.