Explore Air Canada flights from Chicago to Canada from USD 91*
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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.
Best fares between Chicago and Canada
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USD
Chicago (ORD)to
Vancouver (YVR) Jun 24, 2026
From
USD 208
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Aug 15, 2026
From
USD 218
One-way
Economy
Chicago (ORD)to
Toronto (YYZ) Jun 12, 2026
From
USD 91
One-way
Economy
Chicago (ORD)to
Toronto (YYZ) Jun 13, 2026
From
USD 91
One-way
Economy
Chicago (ORD)to
Montréal (YUL) May 13, 2026
From
USD 142
One-way
Economy
Chicago (ORD)to
Montréal (YUL) May 30, 2026
From
USD 142
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Sep 26, 2026
From
USD 111
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Oct 20, 2026
From
USD 111
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Jun 13, 2026
From
USD 91
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Jun 15, 2026
From
USD 91
One-way
Economy
Chicago (ORD)to
Québec (YQB) Jun 23, 2026
From
USD 237
One-way
Economy
Chicago (ORD)to
Québec (YQB) Jun 20, 2026
From
USD 237
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Jun 04, 2026
From
USD 277
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Jun 05, 2026
From
USD 277
One-way
Economy
Chicago (ORD)to
St. John’s, NL (YYT) Jul 19, 2026
From
USD 289
One-way
Economy
Chicago (ORD)to
St. John’s, NL (YYT) Jul 14, 2026
From
USD 289
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Jun 19, 2026
From
USD 288
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Jun 23, 2026
From
USD 288
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) May 27, 2026
From
USD 279
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) May 29, 2026
From
USD 279
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.
Find low fares between Chicago and Canada
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USD
From | To | Fare Type | Departure | Price |
|---|---|---|---|---|
| Chicago (ORD) | Toronto (YYZ) | One-way / Economy | Dec 10, 2026 | From USD 116 Viewed: 1 day ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | Sep 03, 2026 | From USD 218 Viewed: 1 hour ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Jul 28, 2026 | From USD 156 Viewed: 10 hours ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Oct 10, 2026 | From USD 111 Viewed: 1 hour ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | Jan 04, 2027 | From USD 262 Viewed: 1 day ago |
| Chicago (ORD) | Toronto (YTZ) | One-way / Economy | Aug 06, 2026 | From USD 112 Viewed: 1 day ago |
| Chicago (ORD) | Ottawa, ON (YOW) | One-way / Economy | Jul 29, 2026 | From USD 309 Viewed: 9 hours ago |
| Chicago (ORD) | Halifax (YHZ) | One-way / Economy | Feb 06, 2027 | From USD 331 Viewed: 1 day ago |
| Chicago (ORD) | St. John’s, NL (YYT) | One-way / Economy | Aug 08, 2026 | From USD 289 Viewed: 11 hours ago |
| Chicago (ORD) | Winnipeg (YWG) | One-way / Economy | Jul 28, 2026 | From USD 338 Viewed: 20 hours ago |
| Chicago (ORD) | Edmonton (YEG) | One-way / Economy | Sep 29, 2026 | From USD 239 Viewed: 9 hours ago |
| Chicago (ORD) | Charlottetown (YYG) | One-way / Economy | Jul 29, 2026 | From USD 295 Viewed: 22 hours ago |
*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.