Travel with Air Canada from Toronto to Chicago (YTO - ORD) from CAD 199*
*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 | Apr 13, 2026 | From 6,000 pts + CAD 172 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 14, 2026 | From 6,000 pts + CAD 172 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 10, 2026 | From 6,000 pts + CAD 172 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 07, 2026 | From 6,000 pts + CAD 172 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 22, 2026 | From 6,700 pts + CAD 125 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 06, 2026 | From 9,100 pts + CAD 125 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 05, 2026 | From 10,000 pts + CAD 172 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 11, 2026 | From 10,000 pts + CAD 164 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | May 31, 2026 | From 6,000 pts + CAD 172 Viewed: 13 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | May 14, 2026 | From 9,100 pts + CAD 88 Viewed: 16 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 12, 2026 | From 10,000 pts + CAD 163 Viewed: 5 minutes ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Jan 25, 2027 | From 10,000 pts + CAD 159 Viewed: 1 day ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Aug 02, 2026 | From 8,200 pts + CAD 112 Viewed: 13 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.