Book Air Canada flights to Chicago (ORD) from CAD 162*
*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)Montréal (YUL)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Delhi (DEL)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Kelowna (YLW)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 | Apr 09, 2026 | From 6,200 pts + CAD 120 Viewed: 1 day ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Dec 07, 2026 | From 9,200 pts + CAD 124 Viewed: 16 hours ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Jul 20, 2026 | From 11,600 pts + CAD 148 Viewed: 1 day ago |
| Ottawa, ON (YOW) | Chicago (ORD) | One-way / Economy | Sep 21, 2026 | From 10,000 pts + CAD 215 Viewed: 7 hours ago |
| Québec (YQB) | Chicago (ORD) | One-way / Economy | May 02, 2026 | From 9,200 pts + CAD 133 Viewed: 1 day ago |
| Liberia, Costa Rica (LIR) | Chicago (ORD) | One-way / Economy | Apr 04, 2026 | From 48,600 pts + CAD 121 Viewed: 23 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.