Book Air Canada flights to Chicago (ORD) from CAD 176*
*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)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Punta Cana (PUJ)to
Chicago (ORD)Punta Cana (PUJ)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)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)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 | Jan 26, 2027 | From 8,500 pts + CAD 124 Viewed: 1 day ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | May 12, 2026 | From 11,600 pts + CAD 149 Viewed: 1 day ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Jun 26, 2026 | From 9,200 pts + CAD 125 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Jul 04, 2026 | From 11,600 pts + CAD 129 Viewed: 15 hours ago |
| Punta Cana (PUJ) | Chicago (ORD) | One-way / Economy | Dec 24, 2026 | From 15,000 pts + CAD 177 Viewed: 23 hours ago |
| Halifax (YHZ) | Chicago (ORD) | One-way / Economy | May 16, 2026 | From 10,000 pts + CAD 158 Viewed: 1 day ago |
| Québec (YQB) | Chicago (ORD) | One-way / Economy | Jan 01, 2027 | From 10,500 pts + CAD 179 Viewed: 6 hours ago |
| Liberia, Costa Rica (LIR) | Chicago (ORD) | One-way / Economy | Jan 04, 2027 | From 207,300 pts + CAD 358 Viewed: 1 day ago |
| San José, Costa Rica (SJO) | Chicago (ORD) | One-way / Economy | Jan 04, 2027 | From 243,600 pts + CAD 546 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.