Explore Air Canada flights from Chicago to Canada from CAD 169*
*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
Toronto (YYZ)Chicago (ORD)to
Toronto (YYZ)Chicago (ORD)to
Montréal (YUL)Chicago (ORD)to
Montréal (YUL)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
Edmonton (YEG)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
Toronto (YTZ)Chicago (ORD)to
Toronto (YTZ)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Halifax (YHZ)Chicago (ORD)to
Halifax (YHZ)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 19, 2026 | From 6,000 pts + CAD 79 Viewed: 1 day ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | Aug 19, 2026 | From 11,600 pts + CAD 79 Viewed: 1 day ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Oct 07, 2026 | From 10,000 pts + CAD 79 Viewed: 6 minutes ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Oct 13, 2026 | From 12,500 pts + CAD 134 Viewed: 1 day ago |
| Chicago (ORD) | Saskatoon (YXE) | One-way / Economy | Nov 09, 2026 | From 29,200 pts + CAD 134 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.