Book Air Canada flights to Chicago (ORD) from CAD 194*
*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)Calgary (YYC)to
Chicago (ORD)Calgary (YYC)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)Lyon (LYS)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Toronto (YTZ)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 | Jun 20, 2026 | From 6,000 pts + CAD 171 Viewed: 1 day ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Jun 28, 2026 | From 20,200 pts + CAD 250 Viewed: 1 day ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Jun 28, 2026 | From 20,800 pts + CAD 152 Viewed: 13 hours ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Sep 07, 2026 | From 11,600 pts + CAD 168 Viewed: 1 day ago |
| Punta Cana (PUJ) | Chicago (ORD) | One-way / Economy | Nov 29, 2026 | From 93,300 pts + CAD 514 Viewed: 1 day ago |
| Winnipeg (YWG) | Chicago (ORD) | One-way / Economy | Aug 10, 2026 | From 21,700 pts + CAD 217 Viewed: 9 hours ago |
| Québec (YQB) | Chicago (ORD) | One-way / Economy | Jun 21, 2026 | From 21,200 pts + CAD 452 Viewed: 38 minutes ago |
| Liberia, Costa Rica (LIR) | Chicago (ORD) | One-way / Economy | Feb 15, 2027 | From 96,500 pts + CAD 142 Viewed: 1 day ago |
| London, UK (LON) | Chicago (ORD) | Round-trip / Economy | Jul 02, 2026 - Aug 17, 2026 | From 330,000 pts + CAD 3,322 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.