Explore Air Canada flights from Chicago to Canada from CAD 108*
*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
Québec (YQB)Chicago (ORD)to
Québec (YQB)Chicago (ORD)to
Calgary (YYC)Chicago (ORD)to
Calgary (YYC)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
Edmonton (YEG)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)Chicago (ORD)to
Victoria (YYJ)Chicago (ORD)to
Victoria (YYJ)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Ottawa, ON (YOW)*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 17, 2026 | From 6,000 pts + CAD 78 Viewed: 1 day ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | May 24, 2026 | From 11,600 pts + CAD 78 Viewed: 1 day ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | May 11, 2026 | From 10,000 pts + CAD 88 Viewed: 1 day ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Oct 30, 2026 | From 10,200 pts + CAD 91 Viewed: 1 day ago |
| Chicago (ORD) | Halifax (YHZ) | One-way / Economy | Jun 30, 2026 | From 10,000 pts + CAD 83 Viewed: 1 day ago |
| Chicago (ORD) | St. John’s, NL (YYT) | One-way / Economy | Jun 04, 2026 | From 12,500 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.