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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)Halifax (YHZ)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)St. John’s, NL (YYT)to
Chicago (ORD)Moncton (YQM)to
Chicago (ORD)Regina (YQR)to
Chicago (ORD)Saskatoon (YXE)to
Chicago (ORD)Victoria (YYJ)to
Chicago (ORD)Kelowna (YLW)to
Chicago (ORD)London, ON (YXU)to
Chicago (ORD)Charlottetown (YYG)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 | Aug 27, 2024 | 6,000 pts + CAD 155 Viewed: 1 day ago |
| FromVancouver (YVR) | ToChicago (ORD) | One-way / Economy | Aug 15, 2024 | 75,000 pts + CAD 878 Viewed: 1 day ago |
| FromRegina (YQR) | ToChicago (ORD) | One-way / Economy | Nov 02, 2024 | 10,200 pts + CAD 113 Viewed: 1 day ago |
| FromKelowna (YLW) | ToChicago (ORD) | One-way / Economy | Aug 30, 2024 | 25,000 pts + CAD 216 Viewed: 1 day ago |
| FromLiberia, Costa Rica (LIR) | ToChicago (ORD) | One-way / Economy | Jan 25, 2025 | 62,500 pts + CAD 762 Viewed: 8 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.