Book Air Canada flights to Chicago (ORD) from CAD 191*
*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)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)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)
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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 30, 2026 | From 9,900 pts + CAD 163 Viewed: 8 hours ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Feb 15, 2027 | From 12,600 pts + CAD 126 Viewed: 12 hours ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Nov 28, 2026 | From 31,800 pts + CAD 304 Viewed: 1 day ago |
| Frankfurt (FRA) | Chicago (ORD) | Round-trip / Economy | Apr 22, 2027 - May 02, 2027 | From 80,000 pts + CAD 324 Viewed: 9 hours ago |
| Ottawa, ON (YOW) | Chicago (ORD) | One-way / Economy | Dec 18, 2026 | From 10,000 pts + CAD 225 Viewed: 1 day ago |
| Punta Cana (PUJ) | Chicago (ORD) | One-way / Economy | Nov 27, 2026 | From 19,500 pts + CAD 159 Viewed: 1 day ago |
| Liberia, Costa Rica (LIR) | Chicago (ORD) | One-way / Economy | Feb 21, 2027 | From 65,400 pts + CAD 142 Viewed: 1 day ago |
| San José, Costa Rica (SJO) | Chicago (ORD) | One-way / Economy | Apr 03, 2027 | From 12,500 pts + CAD 173 Viewed: 6 hours ago |