Explore Air Canada flights from Chicago to Canada from CAD 173*
*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
Toronto (YTZ)Chicago (ORD)to
Toronto (YTZ)Chicago (ORD)to
Québec (YQB)Chicago (ORD)to
Québec (YQB)Chicago (ORD)to
Halifax (YHZ)Chicago (ORD)to
Halifax (YHZ)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
Winnipeg (YWG)Chicago (ORD)to
Winnipeg (YWG)*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 | Nov 02, 2026 | From 12,000 pts + CAD 161 Viewed: 1 day ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Oct 10, 2026 | From 18,400 pts + CAD 161 Viewed: 1 day ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | Oct 28, 2026 | From 11,600 pts + CAD 81 Viewed: 13 hours ago |
| Chicago (ORD) | Toronto (YTZ) | One-way / Economy | Jun 08, 2027 | From 11,800 pts + CAD 42 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.