Explore Air Canada flights from Chicago to Canada from USD 166*
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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) Nov 24, 2026
From
USD 166
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Nov 01, 2026
From
USD 172
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Nov 05, 2026
From
USD 172
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Apr 13, 2027
From
USD 273
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Apr 21, 2027
From
USD 273
One-way
Economy
Chicago (ORD)to
Toronto (YYZ) Nov 01, 2026
From
USD 166
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Mar 27, 2027
From
USD 191
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Apr 17, 2027
From
USD 191
One-way
Economy
Chicago (ORD)to
Québec (YQB) Jul 07, 2027
From
USD 273
One-way
Economy
Chicago (ORD)to
Québec (YQB) Jan 19, 2027
From
USD 273
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Nov 04, 2026
From
USD 422
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Nov 11, 2026
From
USD 422
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Nov 11, 2026
From
USD 166
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Nov 14, 2026
From
USD 166
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Nov 25, 2026
From
USD 268
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Dec 02, 2026
From
USD 268
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Dec 01, 2026
From
USD 389
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Dec 03, 2026
From
USD 389
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) Nov 10, 2026
From
USD 248
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) Nov 27, 2026
From
USD 248
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 07, 2027 | From USD 273 Viewed: 1 hour ago |
| Chicago (ORD) | Toronto (YYZ) | One-way / Economy | Aug 07, 2027 | From USD 253 Viewed: 17 hours ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | May 11, 2027 | From USD 226 Viewed: 1 day ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Mar 27, 2027 | From USD 191 Viewed: 1 hour ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | Jul 07, 2027 | From USD 273 Viewed: 1 hour ago |
| Chicago (ORD) | Ottawa, ON (YOW) | One-way / Economy | Sep 22, 2027 | From USD 494 Viewed: 1 day ago |
| Chicago (ORD) | Halifax (YHZ) | One-way / Economy | Feb 17, 2027 | From USD 268 Viewed: 1 hour ago |
| Chicago (ORD) | Edmonton (YEG) | One-way / Economy | Apr 10, 2027 | From USD 257 Viewed: 1 day ago |
| Chicago (ORD) | Winnipeg (YWG) | One-way / Economy | Feb 27, 2027 | From USD 502 Viewed: 23 hours ago |
| Chicago (ORD) | Deer Lake (YDF) | One-way / Economy | Jun 16, 2027 | From USD 492 Viewed: 12 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.