Travel with Air Canada from Toronto to Chicago (YTO - ORD) from CAD 193*
*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 | Jun 16, 2026 | From 6,000 pts + CAD 170 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 14, 2026 | From 1,000 pts + CAD 170 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 13, 2026 | From 4,200 pts + CAD 187 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Feb 28, 2026 | From 6,000 pts + CAD 170 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 20, 2026 | From 6,000 pts + CAD 170 Viewed: 3 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Feb 26, 2026 | From 6,000 pts + CAD 170 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 30, 2026 | From 6,000 pts + CAD 170 Viewed: 4 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 27, 2026 | From 6,000 pts + CAD 170 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 06, 2026 | From 6,200 pts + CAD 124 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Feb 10, 2026 | From 10,000 pts + CAD 163 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Feb 27, 2026 | From 10,000 pts + CAD 163 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 02, 2026 | From 12,000 pts + CAD 340 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Feb 13, 2026 | From 20,000 pts + CAD 334 Viewed: 7 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.