Book Air Canada flights to Chicago (ORD) from
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Best fares to Chicago
Toronto (YYZ)to
Chicago (ORD)Montréal (YUL)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)London, ON (YXU)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Regina (YQR)to
Chicago (ORD)Victoria (YYJ)to
Chicago (ORD)St. John’s, NL (YYT)to
Chicago (ORD)Saskatoon (YXE)to
Chicago (ORD)Moncton (YQM)to
Chicago (ORD)Kelowna (YLW)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.
Flights to Chicago - our lowest fares in cash
Toronto (YYZ)to
Chicago (ORD)Montréal (YUL)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)London, ON (YXU)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Regina (YQR)to
Chicago (ORD)Victoria (YYJ)to
Chicago (ORD)St. John’s, NL (YYT)to
Chicago (ORD)Saskatoon (YXE)to
Chicago (ORD)Moncton (YQM)to
Chicago (ORD)Kelowna (YLW)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.
Flights to Chicago - our lowest fares in points
| FromToronto (YYZ) | ToChicago (ORD) | One-way / Economy | Oct 09, 2024 | 6,000 pts + CAD 155 Viewed: 1 day ago |
| FromVancouver (YVR) | ToChicago (ORD) | One-way / Economy | Oct 10, 2024 | 12,500 pts + CAD 139 Viewed: 1 day ago |
| FromCalgary (YYC) | ToChicago (ORD) | One-way / Economy | Dec 22, 2024 | 12,500 pts + CAD 193 Viewed: 1 day ago |
| FromToronto (YTZ) | ToChicago (ORD) | One-way / Economy | Nov 03, 2024 | 11,800 pts + CAD 109 Viewed: 3 hours ago |
| FromLiberia, Costa Rica (LIR) | ToChicago (ORD) | One-way / Economy | Jan 25, 2025 | 35,200 pts + CAD 153 Viewed: 1 day ago |
| FromSan José, Costa Rica (SJO) | ToChicago (ORD) | One-way / Economy | Jan 12, 2025 | 25,000 pts + CAD 302 Viewed: 10 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.