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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)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)Saskatoon (YXE)to
Chicago (ORD)Victoria (YYJ)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Regina (YQR)to
Chicago (ORD)Charlottetown (YYG)to
Chicago (ORD)Moncton (YQM)to
Chicago (ORD)Kelowna (YLW)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
| FromToronto (YYZ) | ToChicago (ORD) | One-way / Economy | Sep 24, 2024 | 6,000 pts + CAD 154 Viewed: 3 hours ago |
| FromMontréal (YUL) | ToChicago (ORD) | One-way / Economy | Dec 28, 2024 | 10,000 pts + CAD 169 Viewed: 1 day ago |
| FromVancouver (YVR) | ToChicago (ORD) | One-way / Economy | Sep 17, 2024 | 12,000 pts + CAD 100 Viewed: 1 day ago |
| FromCalgary (YYC) | ToChicago (ORD) | One-way / Economy | Oct 17, 2024 | 10,200 pts + CAD 157 Viewed: 15 hours ago |
| FromEdmonton (YEG) | ToChicago (ORD) | One-way / Economy | Sep 22, 2024 | 13,500 pts + CAD 118 Viewed: 6 hours ago |
| FromQuébec (YQB) | ToChicago (ORD) | One-way / Economy | Sep 17, 2024 | 10,000 pts + CAD 212 Viewed: 1 day ago |
| FromVictoria (YYJ) | ToChicago (ORD) | One-way / Economy | Sep 17, 2024 | 12,400 pts + CAD 143 Viewed: 1 day ago |
| FromLiberia, Costa Rica (LIR) | ToChicago (ORD) | One-way / Economy | Jan 25, 2025 | 62,500 pts + CAD 757 Viewed: 3 hours ago |
| FromPunta Cana (PUJ) | ToChicago (ORD) | One-way / Economy | Mar 28, 2025 | 12,500 pts + CAD 167 Viewed: 3 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.