Explore Air Canada flights from Chicago to Canada from CAD 149*
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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
Vancouver (YVR) Oct 08, 2026
From
CAD 254
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Oct 09, 2026
From
CAD 254
One-way
Economy
Chicago (ORD)to
Toronto (YYZ) Nov 11, 2026
From
CAD 149
One-way
Economy
Chicago (ORD)to
Toronto (YYZ) Nov 12, 2026
From
CAD 149
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Jan 08, 2027
From
CAD 214
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Jan 09, 2027
From
CAD 214
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Oct 10, 2026
From
CAD 178
One-way
Economy
Chicago (ORD)to
Québec (YQB) Dec 16, 2026
From
CAD 252
One-way
Economy
Chicago (ORD)to
Québec (YQB) Dec 14, 2026
From
CAD 252
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Nov 26, 2026
From
CAD 177
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Oct 17, 2026
From
CAD 449
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Oct 14, 2026
From
CAD 449
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Oct 02, 2026
From
CAD 149
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Sep 29, 2026
From
CAD 149
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Dec 03, 2026
From
CAD 280
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Dec 09, 2026
From
CAD 280
One-way
Economy
Chicago (ORD)to
Kelowna (YLW) Oct 03, 2026
From
CAD 207
One-way
Economy
Chicago (ORD)to
Kelowna (YLW) Oct 06, 2026
From
CAD 213
One-way
Economy
Chicago (ORD)to
Regina (YQR) Dec 13, 2026
From
CAD 220
One-way
Economy
Chicago (ORD)to
Regina (YQR) Dec 15, 2026
From
CAD 220
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 | Dec 28, 2026 | From 6,918 pts + CAD 80 Viewed: 9 hours ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | Feb 19, 2027 | From 14,413 pts + CAD 79 Viewed: 1 day ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Jan 04, 2027 | From 23,062 pts + CAD 158 Viewed: 1 day ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | Dec 26, 2026 | From 20,862 pts + CAD 88 Viewed: 16 hours ago |
| Chicago (ORD) | Ottawa, ON (YOW) | One-way / Economy | Mar 04, 2027 | From 11,531 pts + CAD 80 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.