Book Air Canada flights to Chicago (ORD) from CAD 266*
*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)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Toronto (YTZ)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 | Jul 05, 2027 | From 20,000 pts + CAD 329 Viewed: 18 minutes ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Jun 05, 2027 | From 23,062 pts + CAD 347 Viewed: 15 hours ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | May 30, 2027 | From 28,826 pts + CAD 301 Viewed: 22 hours ago |
| Taipei, Taiwan, China (TPE) | Chicago (ORD) | Round-trip / Economy | Jun 25, 2027 - Jul 17, 2027 | From 100,000 pts + CAD 171 Viewed: 1 day ago |
| Ottawa, ON (YOW) | Chicago (ORD) | One-way / Economy | Feb 19, 2027 | From 11,531 pts + CAD 173 Viewed: 1 hour ago |
| St. John’s, NL (YYT) | Chicago (ORD) | One-way / Economy | Aug 30, 2027 | From 26,665 pts + CAD 198 Viewed: 19 hours ago |