Explore Air Canada flights from Chicago to Canada from USD 75*
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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) Apr 23, 2026
From
USD 209
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Apr 19, 2026
From
USD 209
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Feb 15, 2026
From
USD 75
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Feb 10, 2026
From
USD 75
One-way
Economy
Chicago (ORD)to
Toronto (YYZ) Feb 11, 2026
From
USD 86
One-way
Economy
Chicago (ORD)to
Toronto (YYZ) Feb 14, 2026
From
USD 86
One-way
Economy
Chicago (ORD)to
Calgary (YYC) May 02, 2026
From
USD 86
One-way
Economy
Chicago (ORD)to
Calgary (YYC) May 06, 2026
From
USD 86
One-way
Economy
Chicago (ORD)to
Québec (YQB) Dec 31, 2026
From
USD 240
One-way
Economy
Chicago (ORD)to
Québec (YQB) Jan 01, 2027
From
USD 240
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Feb 15, 2026
From
USD 248
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Feb 23, 2026
From
USD 248
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) Apr 25, 2026
From
USD 142
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) Apr 18, 2026
From
USD 147
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Feb 07, 2026
From
USD 282
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Feb 06, 2026
From
USD 282
One-way
Economy
Chicago (ORD)to
St. John’s, NL (YYT) Jul 01, 2026
From
USD 246
One-way
Economy
Chicago (ORD)to
St. John’s, NL (YYT) Jul 04, 2026
From
USD 246
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Aug 31, 2026
From
USD 315
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Sep 01, 2026
From
USD 315
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) | Vancouver (YVR) | One-way / Economy | Apr 29, 2026 | From USD 209 Viewed: 2 hours ago |
| Chicago (ORD) | Toronto (YYZ) | One-way / Economy | Dec 03, 2026 | From USD 175 Viewed: 3 hours ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Apr 22, 2026 | From USD 153 Viewed: 15 hours ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | Oct 13, 2026 | From USD 240 Viewed: 1 day ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | May 07, 2026 | From USD 86 Viewed: 19 hours ago |
| Chicago (ORD) | Halifax (YHZ) | One-way / Economy | May 17, 2026 | From USD 249 Viewed: 3 hours ago |
| Chicago (ORD) | Edmonton (YEG) | One-way / Economy | Apr 25, 2026 | From USD 142 Viewed: 23 hours ago |
| Chicago (ORD) | Ottawa, ON (YOW) | One-way / Economy | Jun 13, 2026 | From USD 338 Viewed: 1 day ago |
| Chicago (ORD) | St. John’s, NL (YYT) | One-way / Economy | Jun 30, 2026 | From USD 246 Viewed: 1 day ago |
| Chicago (ORD) | Winnipeg (YWG) | One-way / Economy | Sep 04, 2026 | From USD 315 Viewed: 20 hours ago |
| Chicago (ORD) | Charlottetown (YYG) | One-way / Economy | Jun 05, 2026 | From USD 304 Viewed: 1 day ago |
| Chicago (ORD) | Toronto (YTZ) | One-way / Economy | Sep 30, 2026 | From USD 201 Viewed: 1 day ago |
| Chicago (ORD) | Deer Lake (YDF) | One-way / Economy | Jun 01, 2026 | From USD 302 Viewed: 21 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.