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
Toronto (YYZ) Sep 11, 2026
From
USD 112
One-way
Economy
Chicago (ORD)to
Toronto (YYZ) Sep 14, 2026
From
USD 112
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Apr 15, 2026
From
USD 246
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Apr 16, 2026
From
USD 246
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Apr 13, 2026
From
USD 91
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Apr 25, 2026
From
USD 91
One-way
Economy
Chicago (ORD)to
Calgary (YYC) May 06, 2026
From
USD 121
One-way
Economy
Chicago (ORD)to
Calgary (YYC) May 02, 2026
From
USD 121
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Aug 21, 2026
From
USD 374
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Aug 18, 2026
From
USD 374
One-way
Economy
Chicago (ORD)to
Québec (YQB) Oct 14, 2026
From
USD 283
One-way
Economy
Chicago (ORD)to
Québec (YQB) Oct 17, 2026
From
USD 283
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Apr 17, 2026
From
USD 326
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Apr 24, 2026
From
USD 326
One-way
Economy
Chicago (ORD)to
Kelowna (YLW) Apr 16, 2026
From
USD 218
One-way
Economy
Chicago (ORD)to
Kelowna (YLW) Apr 11, 2026
From
USD 286
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) Apr 21, 2026
From
USD 163
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) Apr 24, 2026
From
USD 163
One-way
Economy
Chicago (ORD)to
St. John’s, NL (YYT) Jun 13, 2026
From
USD 297
One-way
Economy
Chicago (ORD)to
St. John’s, NL (YYT) Jun 06, 2026
From
USD 297
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 | Sep 11, 2026 | From USD 112 Viewed: 15 hours ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | Sep 18, 2026 | From USD 273 Viewed: 11 hours ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Sep 19, 2026 | From USD 156 Viewed: 1 day ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Oct 10, 2026 | From USD 151 Viewed: 23 hours ago |
| Chicago (ORD) | Winnipeg (YWG) | One-way / Economy | Aug 17, 2026 | From USD 374 Viewed: 13 hours ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | Oct 18, 2026 | From USD 283 Viewed: 23 hours ago |
| Chicago (ORD) | Edmonton (YEG) | One-way / Economy | Sep 21, 2026 | From USD 313 Viewed: 23 hours ago |
| Chicago (ORD) | Ottawa, ON (YOW) | One-way / Economy | Dec 25, 2026 | From USD 371 Viewed: 1 day ago |
| Chicago (ORD) | St. John’s, NL (YYT) | One-way / Economy | Jun 18, 2026 | From USD 328 Viewed: 1 day ago |
| Chicago (ORD) | Halifax (YHZ) | One-way / Economy | Sep 08, 2026 | From USD 351 Viewed: 15 hours ago |
| Chicago (ORD) | Charlottetown (YYG) | One-way / Economy | Jul 14, 2026 | From USD 304 Viewed: 1 day ago |
| Chicago (ORD) | Deer Lake (YDF) | One-way / Economy | Aug 20, 2026 | From USD 297 Viewed: 12 hours ago |
| Chicago (ORD) | Victoria (YYJ) | One-way / Economy | Jun 22, 2026 | From USD 213 Viewed: 6 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.