Explore Air Canada flights from Chicago to Canada from
† Aeroplan flight bookings are currently only available on the Canadian point of sale. Learn more.
Flights between Chicago and Canada - our lowest fares in cash
Chicago (ORD)to
Vancouver (YVR)Chicago (ORD)to
Toronto (YYZ)Chicago (ORD)to
Montréal (YUL)Chicago (ORD)to
Calgary (YYC)Chicago (ORD)to
Québec (YQB)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
Halifax (YHZ)Chicago (ORD)to
Winnipeg (YWG)Chicago (ORD)to
St. John’s, NL (YYT)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Saskatoon (YXE)Chicago (ORD)to
Charlottetown (YYG)Chicago (ORD)to
Deer Lake (YDF)*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) | ToVancouver (YVR) | One-way / Economy | Sep 18, 2024 | 12,500 pts + CAD 78 Viewed: 1 day ago |
| FromChicago (ORD) | ToToronto (YYZ) | One-way / Economy | Sep 05, 2024 | 6,000 pts + CAD 78 Viewed: 1 day ago |
| FromChicago (ORD) | ToCalgary (YYC) | One-way / Economy | Dec 01, 2024 | 12,500 pts + CAD 127 Viewed: 39 minutes ago |
| FromChicago (ORD) | ToOttawa, ON (YOW) | One-way / Economy | Aug 19, 2024 | 10,000 pts + CAD 120 Viewed: 12 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.