Explore Air Canada flights from Chicago to Canada from CAD 247*
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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) Nov 25, 2026
From
CAD 247
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Nov 10, 2026
From
CAD 388
One-way
Economy
Chicago (ORD)to
Toronto (YYZ) Nov 26, 2026
From
CAD 276
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Nov 15, 2026
From
CAD 254
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Nov 17, 2026
From
CAD 254
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Jul 14, 2027
From
CAD 388
One-way
Economy
Chicago (ORD)to
Québec (YQB) Nov 10, 2026
From
CAD 382
One-way
Economy
Chicago (ORD)to
Québec (YQB) Nov 04, 2026
From
CAD 382
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Dec 08, 2026
From
CAD 261
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Dec 12, 2026
From
CAD 261
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Dec 16, 2026
From
CAD 608
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Dec 12, 2026
From
CAD 608
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Nov 01, 2026
From
CAD 247
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Nov 07, 2026
From
CAD 247
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) Feb 06, 2027
From
CAD 338
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) Feb 09, 2027
From
CAD 338
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Oct 14, 2026
From
CAD 526
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Oct 13, 2026
From
CAD 526
One-way
Economy
Chicago (ORD)to
Saskatoon (YXE) Oct 13, 2026
From
CAD 840
One-way
Economy
Chicago (ORD)to
Saskatoon (YXE) Oct 14, 2026
From
CAD 840
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) | Montréal (YUL) | One-way / Economy | Feb 12, 2027 | From 11,531 pts + CAD 81 Viewed: 1 hour ago |
| Chicago (ORD) | Toronto (YYZ) | One-way / Economy | Feb 18, 2027 | From 6,918 pts + CAD 81 Viewed: 1 day ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | Jul 14, 2027 | From 14,413 pts + CAD 81 Viewed: 23 hours ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | Feb 12, 2027 | From 21,995 pts + CAD 85 Viewed: 1 day ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Jan 05, 2027 | From 28,826 pts + CAD 161 Viewed: 12 hours ago |
| Chicago (ORD) | Halifax (YHZ) | One-way / Economy | Aug 04, 2027 | From 11,531 pts + CAD 81 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.