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
Vancouver (YVR)Chicago (ORD)to
Vancouver (YVR)Chicago (ORD)to
Toronto (YYZ)Chicago (ORD)to
Montréal (YUL)Chicago (ORD)to
Montréal (YUL)Chicago (ORD)to
Toronto (YYZ)Chicago (ORD)to
Calgary (YYC)Chicago (ORD)to
Calgary (YYC)Chicago (ORD)to
Québec (YQB)Chicago (ORD)to
Québec (YQB)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
Winnipeg (YWG)Chicago (ORD)to
Winnipeg (YWG)Chicago (ORD)to
St. John’s, NL (YYT)Chicago (ORD)to
St. John’s, NL (YYT)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
Edmonton (YEG)*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) | Montréal (YUL) | One-way / Economy | Aug 14, 2026 | From 10,000 pts + CAD 79 Viewed: 15 hours ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | Mar 04, 2027 | From 25,000 pts + CAD 158 Viewed: 33 minutes ago |
| Chicago (ORD) | Toronto (YYZ) | One-way / Economy | Sep 07, 2026 | From 6,000 pts + CAD 79 Viewed: 9 minutes ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Sep 05, 2026 | From 23,200 pts + CAD 190 Viewed: 1 hour ago |
| Chicago (ORD) | Toronto (YTZ) | One-way / Economy | Aug 21, 2026 | From 8,700 pts + CAD 40 Viewed: 1 day ago |
| Chicago (ORD) | Winnipeg (YWG) | One-way / Economy | Sep 07, 2026 | From 29,700 pts + CAD 90 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.