Book Air Canada flights to Chicago (ORD) from CAD 186*
*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 to Chicago - our lowest fares in cash
Toronto (YYZ)to
Chicago (ORD)Toronto (YYZ)to
Chicago (ORD)Montréal (YUL)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Montréal (YUL)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)London, UK (LON)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)*Fares displayed have been collected within the last 48hrs 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.
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Flights to Chicago - our lowest fares in points
From | To | Fare Type | Departure | Price |
|---|---|---|---|---|
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Jul 17, 2026 | From 6,000 pts + CAD 172 Viewed: 14 hours ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Jan 04, 2027 | From 11,600 pts + CAD 150 Viewed: 10 hours ago |
| Frankfurt (FRA) | Chicago (ORD) | Round-trip / Economy | Oct 18, 2026 - Nov 01, 2026 | From 79,200 pts + CAD 592 Viewed: 15 hours ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Jul 08, 2026 | From 11,600 pts + CAD 130 Viewed: 1 day ago |
| Munich (MUC) | Chicago (ORD) | Round-trip / Economy | Dec 25, 2026 - Jan 05, 2027 | From 79,600 pts + CAD 530 Viewed: 4 hours ago |
| Copenhagen (CPH) | Chicago (ORD) | Round-trip / Economy | Jul 10, 2026 - Jul 24, 2026 | From 85,600 pts + CAD 347 Viewed: 15 hours ago |
| Liberia, Costa Rica (LIR) | Chicago (ORD) | One-way / Economy | Jan 31, 2027 | From 23,400 pts + CAD 190 Viewed: 7 hours ago |
| San José, Costa Rica (SJO) | Chicago (ORD) | One-way / Economy | Jan 02, 2027 | From 60,200 pts + CAD 131 Viewed: 1 day ago |
| Lyon (LYS) | Chicago (ORD) | Round-trip / Economy | Nov 05, 2026 - Nov 12, 2026 | From 78,000 pts + CAD 305 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.