Book Air Canada flights to Chicago (ORD) from CAD 164*
*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)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)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)Québec (YQB)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Regina (YQR)to
Chicago (ORD)Regina (YQR)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 | Sep 22, 2026 | From 6,000 pts + CAD 168 Viewed: 12 hours ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Aug 27, 2026 | From 12,500 pts + CAD 103 Viewed: 14 hours ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Jul 19, 2026 | From 18,400 pts + CAD 269 Viewed: 19 minutes ago |
| London, UK (LHR) | Chicago (ORD) | Round-trip / Economy | Mar 19, 2026 - Mar 27, 2026 | From 65,300 pts + CAD 372 Viewed: 1 day ago |
| Tel Aviv (TLV) | Chicago (ORD) | Round-trip / Economy | May 04, 2026 - May 18, 2026 | From 220,000 pts + CAD 687 Viewed: 1 day ago |
| Québec (YQB) | Chicago (ORD) | One-way / Economy | Oct 01, 2026 | From 18,400 pts + CAD 446 Viewed: 1 day ago |
| San José, Costa Rica (SJO) | Chicago (ORD) | One-way / Economy | Mar 20, 2026 | From 12,500 pts + CAD 151 Viewed: 14 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.