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 01, 2026
From
CAD 159
One-way
Economy
Chicago (ORD)to
Toronto (YYZ) Sep 02, 2026
From
CAD 159
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Aug 26, 2026
From
CAD 226
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Aug 25, 2026
From
CAD 226
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Sep 08, 2026
From
CAD 285
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Sep 09, 2026
From
CAD 285
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Nov 18, 2026
From
CAD 196
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Nov 24, 2026
From
CAD 196
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Aug 17, 2026
From
CAD 210
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Aug 18, 2026
From
CAD 210
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Sep 02, 2026
From
CAD 419
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Sep 01, 2026
From
CAD 419
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Sep 15, 2026
From
CAD 273
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Sep 16, 2026
From
CAD 273
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) Aug 22, 2026
From
CAD 294
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) Aug 30, 2026
From
CAD 294
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Oct 24, 2026
From
CAD 400
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Oct 21, 2026
From
CAD 400
One-way
Economy
Chicago (ORD)to
St. John’s, NL (YYT) Dec 26, 2026
From
CAD 531
One-way
Economy
Chicago (ORD)to
St. John’s, NL (YYT) Dec 21, 2026
From
CAD 531
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 | May 08, 2027 | From 12,000 pts + CAD 160 Viewed: 1 day ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Dec 20, 2026 | From 10,000 pts + CAD 80 Viewed: 13 hours ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | Oct 22, 2026 | From 11,600 pts + CAD 80 Viewed: 1 day ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Mar 03, 2027 | From 10,000 pts + CAD 130 Viewed: 23 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.