Book Air Canada flights to Chicago (ORD) from CAD 198*
*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.
Flights to Chicago - our lowest fares in cash
Toronto (YYZ)to
Chicago (ORD)Toronto (YYZ)to
Chicago (ORD)Montréal (YUL)to
Chicago (ORD)Montréal (YUL)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Regina (YQR)to
Chicago (ORD)Regina (YQR)to
Chicago (ORD)
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Flights to Chicago - our lowest fares in points
From | To | Fare Type | Departure | Price |
|---|---|---|---|---|
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Mar 29, 2027 | From 6,918 pts + CAD 171 Viewed: 1 day ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Dec 24, 2026 | From 11,531 pts + CAD 172 Viewed: 1 day ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Jun 21, 2027 | From 13,759 pts + CAD 149 Viewed: 1 day ago |
| Québec (YQB) | Chicago (ORD) | One-way / Economy | Dec 26, 2026 | From 23,062 pts + CAD 454 Viewed: 19 hours ago |
| San José, Costa Rica (SJO) | Chicago (ORD) | One-way / Economy | Feb 17, 2027 | From 12,500 pts + CAD 173 Viewed: 1 day ago |
| Winnipeg (YWG) | Chicago (ORD) | One-way / Economy | Dec 22, 2026 | From 11,531 pts + CAD 217 Viewed: 1 day ago |
| Liberia, Costa Rica (LIR) | Chicago (ORD) | One-way / Economy | Apr 10, 2027 | From 166,815 pts + CAD 362 Viewed: 1 day ago |
| Punta Cana (PUJ) | Chicago (ORD) | One-way / Economy | Mar 18, 2027 | From 14,413 pts + CAD 199 Viewed: 16 hours ago |