Explore Air Canada flights from Chicago to Canada from CAD 142*
*Fares displayed have been collected within the last 48 hours and may no longer be available at the 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
Montréal (YUL)Chicago (ORD)to
Montréal (YUL)Chicago (ORD)to
Toronto (YYZ)Chicago (ORD)to
Toronto (YYZ)Chicago (ORD)to
Vancouver (YVR)Chicago (ORD)to
Vancouver (YVR)Chicago (ORD)to
Calgary (YYC)Chicago (ORD)to
Calgary (YYC)Chicago (ORD)to
Québec (YQB)Chicago (ORD)to
Québec (YQB)Chicago (ORD)to
Winnipeg (YWG)Chicago (ORD)to
Winnipeg (YWG)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Kelowna (YLW)Chicago (ORD)to
Kelowna (YLW)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
St. John’s, NL (YYT)Chicago (ORD)to
St. John’s, NL (YYT)*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
From | To | Fare Type | Departure | Price |
|---|---|---|---|---|
| Chicago (ORD) | Toronto (YYZ) | One-way / Economy | Aug 14, 2026 | From 6,000 pts + CAD 79 Viewed: 1 day ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | Aug 02, 2026 | From 23,200 pts + CAD 158 Viewed: 1 day ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Jul 01, 2026 | From 9,200 pts + CAD 79 Viewed: 18 hours ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Nov 21, 2026 | From 65,500 pts + CAD 255 Viewed: 7 hours ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | Oct 13, 2026 | From 15,000 pts + CAD 79 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.