*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
Chicago (ORD)to
Toronto (YYZ)Chicago (ORD)to
Vancouver (YVR)Chicago (ORD)to
Montréal (YUL)Chicago (ORD)to
Calgary (YYC)Chicago (ORD)to
Toronto (YTZ)Chicago (ORD)to
Québec (YQB)Chicago (ORD)to
Ottawa, ON (YOW)Chicago (ORD)to
Halifax (YHZ)Chicago (ORD)to
St. John’s, NL (YYT)Chicago (ORD)to
Edmonton (YEG)Chicago (ORD)to
Winnipeg (YWG)Chicago (ORD)to
Kelowna (YLW)Chicago (ORD)to
Deer Lake (YDF)Chicago (ORD)to
Saskatoon (YXE)*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
From | To | Fare Type | Departure | Price |
|---|---|---|---|---|
| Chicago (ORD) | Toronto (YYZ) | One-way / Economy | Aug 08, 2026 | From CAD 168 Viewed: 1 day ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | Sep 08, 2026 | From CAD 260 Viewed: 1 day ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Sep 05, 2026 | From CAD 249 Viewed: 1 day ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Jul 21, 2026 | From CAD 168 Viewed: 6 hours ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | Sep 17, 2026 | From CAD 354 Viewed: 15 hours ago |
| Chicago (ORD) | Ottawa, ON (YOW) | One-way / Economy | Jul 22, 2026 | From CAD 432 Viewed: 14 hours ago |
| Chicago (ORD) | Winnipeg (YWG) | One-way / Economy | Nov 06, 2026 | From CAD 503 Viewed: 1 day 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.
Check out popular routes from Chicago to Canada
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