Travel with Air Canada from Toronto to Chicago (YTO - ORD) from CAD 188*
*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 | Jun 12, 2026 | From 6,000 pts + CAD 171 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 13, 2026 | From 6,000 pts + CAD 171 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Aug 30, 2026 | From 6,000 pts + CAD 172 Viewed: 18 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 10, 2026 | From 6,000 pts + CAD 171 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 26, 2026 | From 6,400 pts + CAD 172 Viewed: 13 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 27, 2026 | From 9,100 pts + CAD 125 Viewed: 19 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 25, 2026 | From 9,100 pts + CAD 125 Viewed: 13 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 15, 2026 | From 10,000 pts + CAD 171 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 20, 2026 | From 10,000 pts + CAD 164 Viewed: 13 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 27, 2026 | From 10,000 pts + CAD 171 Viewed: 1 day ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 24, 2026 | From 10,000 pts + CAD 164 Viewed: 10 hours ago |
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jun 19, 2026 | From 24,000 pts + CAD 684 Viewed: 1 day ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Jul 17, 2026 | From 6,700 pts + CAD 112 Viewed: 8 hours ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Aug 03, 2026 | From 8,300 pts + CAD 112 Viewed: 17 hours ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Jun 23, 2026 | From 8,400 pts + CAD 112 Viewed: 1 day ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Jul 03, 2026 | From 13,400 pts + CAD 224 Viewed: 16 hours ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Jun 25, 2026 | From 13,400 pts + CAD 112 Viewed: 1 day ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Jul 02, 2026 | From 16,600 pts + CAD 224 Viewed: 16 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.