Explore Air Canada flights from Chicago to Canada from CAD 121*
*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
Québec (YQB)Chicago (ORD)to
Québec (YQB)Chicago (ORD)to
Halifax (YHZ)Chicago (ORD)to
Halifax (YHZ)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Charlottetown (YYG)Chicago (ORD)to
Charlottetown (YYG)Chicago (ORD)to
Saskatoon (YXE)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 | Jun 04, 2026 | From 6,000 pts + CAD 79 Viewed: 12 hours ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Oct 16, 2026 | From 10,000 pts + CAD 79 Viewed: 12 hours ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Aug 04, 2026 | From 11,600 pts + CAD 90 Viewed: 8 hours ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | Sep 01, 2026 | From 20,800 pts + CAD 167 Viewed: 1 day ago |
| Chicago (ORD) | Halifax (YHZ) | One-way / Economy | Jul 17, 2026 | From 24,900 pts + CAD 95 Viewed: 1 day ago |
| Chicago (ORD) | St. John’s, NL (YYT) | One-way / Economy | Jun 27, 2026 | From 20,900 pts + CAD 45 Viewed: 5 hours ago |
| Chicago (ORD) | Victoria (YYJ) | One-way / Economy | Jun 08, 2026 | From 12,500 pts + CAD 67 Viewed: 13 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.