Explore Air Canada flights from Chicago to Canada from CAD 170*
*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
Vancouver (YVR)Chicago (ORD)to
Vancouver (YVR)Chicago (ORD)to
Montréal (YUL)Chicago (ORD)to
Montréal (YUL)Chicago (ORD)to
Calgary (YYC)Chicago (ORD)to
Calgary (YYC)Chicago (ORD)to
Toronto (YTZ)Chicago (ORD)to
Toronto (YTZ)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
Edmonton (YEG)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
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 | Oct 11, 2026 | From 12,000 pts + CAD 159 Viewed: 19 hours ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Dec 10, 2026 | From 10,000 pts + CAD 80 Viewed: 1 day ago |
| Chicago (ORD) | Halifax (YHZ) | One-way / Economy | May 23, 2027 | From 34,800 pts + CAD 45 Viewed: 10 hours ago |
| Chicago (ORD) | Winnipeg (YWG) | One-way / Economy | Sep 21, 2026 | From 20,000 pts + CAD 269 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.