Book Air Canada flights to Chicago (ORD) from CAD 181*
*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)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Winnipeg (YWG)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 |
|---|---|---|---|---|
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Apr 01, 2027 | From 12,100 pts + CAD 124 Viewed: 1 day ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Aug 31, 2026 | From 40,000 pts + CAD 686 Viewed: 1 day ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Feb 15, 2027 | From 11,300 pts + CAD 149 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Sep 27, 2026 | From 10,800 pts + CAD 168 Viewed: 1 day ago |
| Québec (YQB) | Chicago (ORD) | One-way / Economy | Jan 04, 2027 | From 13,900 pts + CAD 179 Viewed: 1 day ago |
| San José, Costa Rica (SJO) | Chicago (ORD) | One-way / Economy | Nov 28, 2026 | From 58,400 pts + CAD 271 Viewed: 20 hours ago |
| Victoria (YYJ) | Chicago (ORD) | One-way / Economy | Jul 30, 2026 | From 16,900 pts + CAD 183 Viewed: 11 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.