Book Air Canada flights to Chicago (ORD) from CAD 178*
*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)Winnipeg (YWG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Kelowna (YLW)to
Chicago (ORD)Kelowna (YLW)to
Chicago (ORD)*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.
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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, 2026 | From 9,300 pts + CAD 170 Viewed: 1 day ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Oct 20, 2026 | From 10,000 pts + CAD 172 Viewed: 21 hours ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Aug 01, 2026 | From 11,600 pts + CAD 195 Viewed: 1 day ago |
| Ottawa, ON (YOW) | Chicago (ORD) | One-way / Economy | Dec 14, 2026 | From 10,000 pts + CAD 165 Viewed: 16 hours ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Sep 08, 2026 | From 10,700 pts + CAD 181 Viewed: 1 day ago |
| Halifax (YHZ) | Chicago (ORD) | One-way / Economy | Jun 08, 2026 | From 10,000 pts + CAD 169 Viewed: 16 hours ago |
*Points displayed do not reflect preferred pricing for Aeroplan Elite Status Members and/or Aeroplan Credit Cardholders. Prices have been collected within the past 48 hrs and may no longer be available at time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.