Book Air Canada flights to Chicago (ORD) from CAD 179*
*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)Calgary (YYC)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Bangkok (BKK)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Winnipeg (YWG)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 24, 2026 | From 6,000 pts + CAD 171 Viewed: 16 minutes ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Apr 26, 2026 | From 11,600 pts + CAD 150 Viewed: 1 day ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | May 25, 2026 | From 47,800 pts + CAD 252 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Jul 11, 2026 | From 9,400 pts + CAD 168 Viewed: 2 hours ago |
| Québec (YQB) | Chicago (ORD) | One-way / Economy | May 30, 2026 | From 9,200 pts + CAD 137 Viewed: 17 hours ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Jun 28, 2026 | From 10,000 pts + CAD 159 Viewed: 22 hours ago |
| Regina (YQR) | Chicago (ORD) | One-way / Economy | Aug 08, 2026 | From 37,500 pts + CAD 473 Viewed: 1 day ago |
| Liberia, Costa Rica (LIR) | Chicago (ORD) | One-way / Economy | Jun 24, 2026 | From 60,000 pts + CAD 627 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.