Explore Air Canada flights from Chicago to Canada from CAD 142*

Promotion code

*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

CAD
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Chicago (ORD)to

Vancouver (YVR)
Jun 23, 2026
From
CAD 291
One-way
Economy

Chicago (ORD)to

Vancouver (YVR)
Jun 24, 2026
From
CAD 291
One-way
Economy

Chicago (ORD)to

Toronto (YYZ)
May 30, 2026
From
CAD 142
One-way
Economy

Chicago (ORD)to

Montréal (YUL)
Jun 17, 2026
From
CAD 206
One-way
Economy

Chicago (ORD)to

Montréal (YUL)
Jun 16, 2026
From
CAD 206
One-way
Economy

Chicago (ORD)to

Toronto (YYZ)
May 16, 2026
From
CAD 142
One-way
Economy

Chicago (ORD)to

Calgary (YYC)
Jul 22, 2026
From
CAD 167
One-way
Economy

Chicago (ORD)to

Calgary (YYC)
Jul 21, 2026
From
CAD 167
One-way
Economy

Chicago (ORD)to

Québec (YQB)
May 10, 2026
From
CAD 322
One-way
Economy

Chicago (ORD)to

Québec (YQB)
May 13, 2026
From
CAD 322
One-way
Economy

Chicago (ORD)to

Toronto (YTZ)
Jun 21, 2026
From
CAD 142
One-way
Economy

Chicago (ORD)to

Toronto (YTZ)
Jun 18, 2026
From
CAD 142
One-way
Economy

Chicago (ORD)to

Ottawa, ON (YOW)
Jul 13, 2026
From
CAD 407
One-way
Economy

Chicago (ORD)to

Ottawa, ON (YOW)
Jul 10, 2026
From
CAD 407
One-way
Economy

Chicago (ORD)to

Winnipeg (YWG)
Jun 20, 2026
From
CAD 388
One-way
Economy

Chicago (ORD)to

Winnipeg (YWG)
Jul 12, 2026
From
CAD 412
One-way
Economy

Chicago (ORD)to

St. John’s, NL (YYT)
May 13, 2026
From
CAD 396
One-way
Economy

Chicago (ORD)to

St. John’s, NL (YYT)
May 16, 2026
From
CAD 403
One-way
Economy

Chicago (ORD)to

Edmonton (YEG)
Jun 17, 2026
From
CAD 219
One-way
Economy

Chicago (ORD)to

Edmonton (YEG)
Jun 20, 2026
From
CAD 219
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 from Chicago to Canada | Air Canada

Flights between Chicago and Canada - our lowest fares in points

pts
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Flights between Chicago and Canada - our lowest fares in points
From
To
Fare Type
Departure
Price
Chicago (ORD)Montréal (YUL)One-way
/
Economy
Aug 14, 2026

From

10,000 pts
+ CAD 79

Viewed: 15 hours ago

Chicago (ORD)Vancouver (YVR)One-way
/
Economy
Mar 04, 2027

From

25,000 pts
+ CAD 158

Viewed: 33 minutes ago

Chicago (ORD)Toronto (YYZ)One-way
/
Economy
Sep 07, 2026

From

6,000 pts
+ CAD 79

Viewed: 9 minutes ago

Chicago (ORD)Calgary (YYC)One-way
/
Economy
Sep 05, 2026

From

23,200 pts
+ CAD 190

Viewed: 1 hour ago

Chicago (ORD)Toronto (YTZ)One-way
/
Economy
Aug 21, 2026

From

8,700 pts
+ CAD 40

Viewed: 1 day ago

Chicago (ORD)Winnipeg (YWG)One-way
/
Economy
Sep 07, 2026

From

29,700 pts
+ CAD 90

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.