Book Air Canada flights to Chicago (ORD) from CAD 163*
*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)Vancouver (YVR)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Montréal (YUL)to
Chicago (ORD)Montréal (YUL)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Kelowna (YLW)to
Chicago (ORD)Kelowna (YLW)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)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 | Jun 18, 2026 | From 8,700 pts + CAD 120 Viewed: 1 day ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Mar 28, 2026 | From 8,000 pts + CAD 134 Viewed: 22 hours ago |
| Athens (ATH) | Chicago (ORD) | Round-trip / Economy | Apr 16, 2026 - Apr 26, 2026 | From 158,000 pts + CAD 597 Viewed: 5 hours ago |
| Québec (YQB) | Chicago (ORD) | One-way / Economy | Nov 09, 2026 | From 18,400 pts + CAD 258 Viewed: 20 hours ago |
| Liberia, Costa Rica (LIR) | Chicago (ORD) | One-way / Economy | Mar 27, 2026 | From 145,800 pts + CAD 1,096 Viewed: 1 day ago |
| Punta Cana (PUJ) | Chicago (ORD) | One-way / Economy | Mar 28, 2026 | From 12,500 pts + CAD 187 Viewed: 6 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.