Book Air Canada flights to Chicago (ORD) from CAD 188*
*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)Delhi (DEL)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)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)*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 |
|---|---|---|---|---|
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Sep 12, 2026 | From 11,600 pts + CAD 150 Viewed: 4 hours ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Oct 24, 2026 | From 10,000 pts + CAD 173 Viewed: 1 day ago |
| Ottawa, ON (YOW) | Chicago (ORD) | One-way / Economy | Oct 24, 2026 | From 10,000 pts + CAD 171 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Nov 01, 2026 | From 14,100 pts + CAD 168 Viewed: 16 hours ago |
| Winnipeg (YWG) | Chicago (ORD) | One-way / Economy | Nov 07, 2026 | From 10,000 pts + CAD 218 Viewed: 8 hours ago |
| Punta Cana (PUJ) | Chicago (ORD) | One-way / Economy | Jan 18, 2027 | From 12,500 pts + CAD 185 Viewed: 1 day ago |
| Liberia, Costa Rica (LIR) | Chicago (ORD) | One-way / Economy | Mar 26, 2027 | From 119,600 pts + CAD 485 Viewed: 12 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.