Explore Air Canada flights from Chicago to Canada from
† Aeroplan flight bookings are currently only available on the Canadian point of sale. Learn more.
Best fares between Chicago and Canada
Chicago (ORD)to
Toronto (YYZ)Chicago (ORD)to
Montréal (YUL)Chicago (ORD)to
Vancouver (YVR)Chicago (ORD)to
Calgary (YYC)Chicago (ORD)to
Québec (YQB)Chicago (ORD)to
Halifax (YHZ)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
Winnipeg (YWG)Chicago (ORD)to
Victoria (YYJ)Chicago (ORD)to
Saskatoon (YXE)*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 between Chicago and Canada - our lowest fares in cash
Chicago (ORD)to
Toronto (YYZ)Chicago (ORD)to
Montréal (YUL)Chicago (ORD)to
Vancouver (YVR)Chicago (ORD)to
Calgary (YYC)Chicago (ORD)to
Québec (YQB)Chicago (ORD)to
Halifax (YHZ)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
Kelowna (YLW)Chicago (ORD)to
Winnipeg (YWG)Chicago (ORD)to
Victoria (YYJ)Chicago (ORD)to
Saskatoon (YXE)*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 between Chicago and Canada - our lowest fares in points
| FromChicago (ORD) | ToMontréal (YUL) | One-way / Economy | Nov 08, 2024 | 10,000 pts + CAD 77 Viewed: 1 day ago |
| FromChicago (ORD) | ToToronto (YYZ) | One-way / Economy | Nov 19, 2024 | 6,000 pts + CAD 77 Viewed: 1 day ago |
| FromChicago (ORD) | ToCalgary (YYC) | One-way / Economy | Jul 04, 2025 | 30,800 pts + CAD 38 Viewed: 12 hours ago |
| FromChicago (ORD) | ToQuébec (YQB) | One-way / Economy | Feb 15, 2025 | 10,000 pts + CAD 77 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.