Book Air Canada flights to Chicago (ORD) from CAD 192*
*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)Toronto (YTZ)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)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 | Dec 19, 2026 | From 6,000 pts + CAD 172 Viewed: 8 hours ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Jul 13, 2027 | From 11,300 pts + CAD 115 Viewed: 1 day ago |
| Ottawa, ON (YOW) | Chicago (ORD) | One-way / Economy | Apr 02, 2027 | From 10,000 pts + CAD 172 Viewed: 1 day ago |
| Punta Cana (PUJ) | Chicago (ORD) | One-way / Economy | Nov 15, 2026 | From 39,600 pts + CAD 346 Viewed: 9 hours ago |
| Liberia, Costa Rica (LIR) | Chicago (ORD) | One-way / Economy | Apr 11, 2027 | From 28,500 pts + CAD 123 Viewed: 13 hours ago |