Explore Air Canada flights from Chicago to Canada from CAD 159*
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1 Passenger
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*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
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CAD
Chicago (ORD)to
Toronto (YYZ) Sep 09, 2026
From
CAD 159
One-way
Economy
Chicago (ORD)to
Toronto (YYZ) Sep 08, 2026
From
CAD 159
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Oct 26, 2026
From
CAD 238
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Oct 27, 2026
From
CAD 238
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Nov 10, 2026
From
CAD 299
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Nov 11, 2026
From
CAD 299
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Sep 30, 2026
From
CAD 228
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Sep 29, 2026
From
CAD 228
One-way
Economy
Chicago (ORD)to
Québec (YQB) Oct 06, 2026
From
CAD 292
One-way
Economy
Chicago (ORD)to
Québec (YQB) Oct 07, 2026
From
CAD 292
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Sep 16, 2026
From
CAD 286
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Sep 22, 2026
From
CAD 286
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Sep 02, 2026
From
CAD 423
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Sep 01, 2026
From
CAD 423
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Sep 21, 2026
From
CAD 410
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Sep 22, 2026
From
CAD 410
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Sep 01, 2026
From
CAD 159
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Sep 02, 2026
From
CAD 159
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) Sep 19, 2026
From
CAD 337
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) Sep 23, 2026
From
CAD 337
One-way
Economy
*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
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pts
From | To | Fare Type | Departure | Price |
|---|---|---|---|---|
| Chicago (ORD) | Toronto (YYZ) | One-way / Economy | Nov 21, 2026 | From 24,000 pts + CAD 320 Viewed: 22 hours ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Dec 05, 2026 | From 20,000 pts + CAD 160 Viewed: 8 hours ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | Dec 12, 2026 | From 12,500 pts + CAD 80 Viewed: 23 hours ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | Dec 05, 2026 | From 20,000 pts + CAD 270 Viewed: 8 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.