Travel with Air Canada from Toronto to Chicago (YTO - ORD) from CAD 185*
*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 | May 23, 2026 | From 6,000 pts + CAD 170 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 21, 2026 | From 6,000 pts + CAD 170 Viewed: 18 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 15, 2026 | From 6,000 pts + CAD 170 Viewed: 23 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 14, 2026 | From 6,000 pts + CAD 170 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 07, 2026 | From 6,000 pts + CAD 170 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 10, 2026 | From 6,000 pts + CAD 170 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | May 24, 2026 | From 6,000 pts + CAD 170 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 27, 2026 | From 6,000 pts + CAD 170 Viewed: 23 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | May 20, 2026 | From 6,000 pts + CAD 170 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 26, 2026 | From 10,000 pts + CAD 163 Viewed: 12 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 06, 2026 | From 10,000 pts + CAD 163 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 12, 2026 | From 20,000 pts + CAD 340 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 29, 2026 | From 6,000 pts + CAD 170 Viewed: 3 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 24, 2026 | From 6,000 pts + CAD 170 Viewed: 13 minutes ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 23, 2026 | From 10,000 pts + CAD 163 Viewed: 13 minutes ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 22, 2026 | From 10,000 pts + CAD 163 Viewed: 1 day ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Jul 12, 2026 | From 6,700 pts + CAD 111 Viewed: 2 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.