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 | Jul 03, 2026 | From 6,000 pts + CAD 171 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 06, 2026 | From 6,000 pts + CAD 171 Viewed: 14 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 16, 2026 | From 6,000 pts + CAD 171 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Aug 01, 2026 | From 6,000 pts + CAD 171 Viewed: 15 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | May 22, 2026 | From 6,000 pts + CAD 171 Viewed: 19 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Oct 04, 2026 | From 6,000 pts + CAD 171 Viewed: 7 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Aug 14, 2026 | From 6,000 pts + CAD 171 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Sep 03, 2026 | From 8,100 pts + CAD 124 Viewed: 19 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 22, 2026 | From 9,900 pts + CAD 88 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Aug 16, 2026 | From 10,000 pts + CAD 171 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 11, 2026 | From 12,000 pts + CAD 341 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | May 28, 2026 | From 12,000 pts + CAD 341 Viewed: 1 day ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Sep 12, 2026 | From 7,600 pts + CAD 112 Viewed: 19 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.