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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)Halifax (YHZ)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Saskatoon (YXE)to
Chicago (ORD)London, UK (LON)to
Chicago (ORD)St. John’s, NL (YYT)to
Chicago (ORD)Regina (YQR)to
Chicago (ORD)Victoria (YYJ)to
Chicago (ORD)Seoul (ICN)to
Chicago (ORD)Kelowna (YLW)to
Chicago (ORD)Moncton (YQM)to
Chicago (ORD)London, ON (YXU)to
Chicago (ORD)San José, Costa Rica (SJO)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 | Sep 07, 2024 | 6,000 pts + CAD 155 Viewed: 22 hours ago |
| FromVancouver (YVR) | ToChicago (ORD) | One-way / Economy | Mar 15, 2025 | 12,500 pts + CAD 171 Viewed: 1 day ago |
| FromMontréal (YUL) | ToChicago (ORD) | One-way / Economy | Dec 02, 2024 | 9,400 pts + CAD 179 Viewed: 17 hours ago |
| FromOttawa, ON (YOW) | ToChicago (ORD) | One-way / Economy | Aug 14, 2024 | 10,000 pts + CAD 162 Viewed: 3 hours ago |
| FromCalgary (YYC) | ToChicago (ORD) | One-way / Economy | Sep 19, 2024 | 20,400 pts + CAD 314 Viewed: 21 hours ago |
| FromLiberia, Costa Rica (LIR) | ToChicago (ORD) | One-way / Economy | Jan 25, 2025 | 12,500 pts + CAD 153 Viewed: 3 hours ago |
| FromSaskatoon (YXE) | ToChicago (ORD) | One-way / Economy | Sep 20, 2024 | 10,400 pts + CAD 157 Viewed: 19 hours ago |
| FromSan José, Costa Rica (SJO) | ToChicago (ORD) | One-way / Economy | Feb 16, 2025 | 25,000 pts + CAD 318 Viewed: 19 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.