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 01, 2026 | From 6,000 pts + CAD 170 Viewed: 17 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 23, 2026 | From 7,600 pts + CAD 123 Viewed: 15 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 05, 2026 | From 12,000 pts + CAD 340 Viewed: 22 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 04, 2026 | From 12,000 pts + CAD 340 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | May 14, 2026 | From 6,700 pts + CAD 124 Viewed: 1 hour ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | May 10, 2026 | From 6,000 pts + CAD 170 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | May 15, 2026 | From 6,000 pts + CAD 170 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 01, 2026 | From 6,000 pts + CAD 170 Viewed: 1 day ago |
| 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 | Jun 04, 2026 | From 6,700 pts + CAD 124 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 13, 2026 | From 9,200 pts + CAD 187 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 30, 2026 | From 10,000 pts + CAD 163 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 21, 2026 | From 10,000 pts + CAD 163 Viewed: 1 day ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Jun 24, 2026 | From 6,700 pts + CAD 111 Viewed: 12 hours ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Jul 15, 2026 | From 6,700 pts + CAD 111 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.