Travel with Air Canada from Toronto to Chicago (YTO - ORD) from CAD 202*
*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 04, 2026 | From 6,000 pts + CAD 173 Viewed: 1 hour ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 03, 2026 | From 10,000 pts + CAD 173 Viewed: 36 minutes ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 14, 2026 | From 6,000 pts + CAD 173 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 13, 2026 | From 6,000 pts + CAD 173 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 30, 2026 | From 10,000 pts + CAD 165 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 06, 2026 | From 10,000 pts + CAD 165 Viewed: 20 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 05, 2026 | From 10,000 pts + CAD 165 Viewed: 14 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 02, 2026 | From 12,000 pts + CAD 380 Viewed: 13 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Oct 14, 2026 | From 12,000 pts + CAD 380 Viewed: 13 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 12, 2026 | From 18,000 pts + CAD 173 Viewed: 17 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 01, 2026 | From 20,000 pts + CAD 356 Viewed: 13 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Aug 10, 2026 | From 22,200 pts + CAD 278 Viewed: 13 hours ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Jul 10, 2026 | From 10,000 pts + CAD 161 Viewed: 21 hours ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Sep 03, 2026 | From 8,600 pts + CAD 114 Viewed: 1 day ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Aug 30, 2026 | From 9,500 pts + CAD 114 Viewed: 1 day ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Aug 19, 2026 | From 22,800 pts + CAD 340 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.