Book Air Canada flights to Chicago (ORD) from CAD 201*
*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)Ottawa, ON (YOW)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)
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Flights to Chicago - our lowest fares in points
From | To | Fare Type | Departure | Price |
|---|---|---|---|---|
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Nov 01, 2026 | From 10,000 pts + CAD 177 Viewed: 23 hours ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | May 15, 2027 | From 11,600 pts + CAD 151 Viewed: 4 hours ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Oct 27, 2026 | From 11,600 pts + CAD 124 Viewed: 1 day ago |
| Seoul (ICN) | Chicago (ORD) | Round-trip / Economy | Mar 17, 2027 - May 19, 2027 | From 124,200 pts + CAD 185 Viewed: 1 day ago |
| Halifax (YHZ) | Chicago (ORD) | One-way / Economy | Mar 17, 2027 | From 40,000 pts + CAD 637 Viewed: 1 day ago |
| Québec (YQB) | Chicago (ORD) | One-way / Economy | Oct 25, 2026 | From 10,000 pts + CAD 228 Viewed: 9 hours ago |
| London, UK (LON) | Chicago (ORD) | Round-trip / Economy | May 29, 2027 - Jun 09, 2027 | From 330,800 pts + CAD 1,752 Viewed: 16 hours ago |
| San José, Costa Rica (SJO) | Chicago (ORD) | One-way / Economy | Jan 08, 2027 | From 49,800 pts + CAD 139 Viewed: 5 hours ago |