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Flights to Chicago - our lowest fares in cash
Toronto (YYZ)to
Chicago (ORD)Montreal (YUL)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Victoria (YYJ)to
Chicago (ORD)Copenhagen (CPH)to
Chicago (ORD)Saskatoon (YXE)to
Chicago (ORD)Kelowna (YLW)to
Chicago (ORD)St. John’s, NL (YYT)to
Chicago (ORD)Regina (YQR)to
Chicago (ORD)Moncton (YQM)to
Chicago (ORD)London, ON (YXU)to
Chicago (ORD)Toronto (YTZ)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 | Feb 11, 2025 | 6,000 pts + CAD 151 Viewed: 1 day ago |
| FromVancouver (YVR) | ToChicago (ORD) | One-way / Economy | Sep 10, 2024 | 11,400 pts + CAD 96 Viewed: 21 hours ago |
| FromMontreal (YUL) | ToChicago (ORD) | One-way / Economy | Mar 25, 2025 | 10,100 pts + CAD 119 Viewed: 1 day ago |
| FromCalgary (YYC) | ToChicago (ORD) | One-way / Economy | Sep 02, 2024 | 9,900 pts + CAD 114 Viewed: 21 hours ago |
| FromOttawa, ON (YOW) | ToChicago (ORD) | One-way / Economy | Mar 25, 2025 | 11,300 pts + CAD 120 Viewed: 1 day ago |
| FromEdmonton (YEG) | ToChicago (ORD) | One-way / Economy | Aug 16, 2024 | 51,200 pts + CAD 456 Viewed: 1 day ago |
| FromWinnipeg (YWG) | ToChicago (ORD) | One-way / Economy | Dec 25, 2024 | 11,600 pts + CAD 162 Viewed: 1 day ago |
| FromSan José, Costa Rica (SJO) | ToChicago (ORD) | One-way / Economy | Oct 26, 2024 | 12,500 pts + CAD 154 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.