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
Montréal (YUL)Chicago (ORD)to
Montréal (YUL)Chicago (ORD)to
Vancouver (YVR)Chicago (ORD)to
Vancouver (YVR)Chicago (ORD)to
Toronto (YYZ)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
Ottawa, ON (YOW)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Victoria (YYJ)Chicago (ORD)to
Victoria (YYJ)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) | Vancouver (YVR) | One-way / Economy | Jul 11, 2026 | From 11,600 pts + CAD 78 Viewed: 1 day ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Oct 05, 2026 | From 20,000 pts + CAD 156 Viewed: 1 day ago |
| Chicago (ORD) | Toronto (YYZ) | One-way / Economy | Dec 17, 2026 | From 15,300 pts + CAD 39 Viewed: 22 hours ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | May 11, 2026 | From 10,000 pts + CAD 88 Viewed: 2 hours ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Oct 30, 2026 | From 10,200 pts + CAD 91 Viewed: 5 hours ago |
| Chicago (ORD) | St. John’s, NL (YYT) | One-way / Economy | Jun 04, 2026 | From 12,500 pts + CAD 134 Viewed: 4 hours 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.