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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)Halifax (YHZ)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)London, UK (LHR)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Victoria (YYJ)to
Chicago (ORD)Saskatoon (YXE)to
Chicago (ORD)Kelowna (YLW)to
Chicago (ORD)Regina (YQR)to
Chicago (ORD)St. John’s, NL (YYT)to
Chicago (ORD)Moncton (YQM)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)London, ON (YXU)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
| FromVancouver (YVR) | ToChicago (ORD) | One-way / Economy | Aug 21, 2024 | 11,400 pts + CAD 96 Viewed: 18 hours ago |
| FromCalgary (YYC) | ToChicago (ORD) | One-way / Economy | Feb 16, 2025 | 12,300 pts + CAD 122 Viewed: 1 day ago |
| FromQuébec (YQB) | ToChicago (ORD) | One-way / Economy | Feb 21, 2025 | 48,500 pts + CAD 759 Viewed: 5 hours ago |
| FromSan José, Costa Rica (SJO) | ToChicago (ORD) | One-way / Economy | Mar 27, 2025 | 77,500 pts + CAD 121 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.