Book Air Canada flights to Chicago (ORD) from CAD 179*
Flights to Chicago - our lowest fares in cash
Toronto (YYZ)to
Chicago (ORD)Montréal (YUL)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Victoria (YYJ)to
Chicago (ORD)Saskatoon (YXE)to
Chicago (ORD)St. John’s, NL (YYT)to
Chicago (ORD)Moncton (YQM)to
Chicago (ORD)Regina (YQR)to
Chicago (ORD)Kelowna (YLW)to
Chicago (ORD)London, ON (YXU)to
Chicago (ORD)Stockholm (ARN)to
Chicago (ORD)Bathurst (ZBF)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.
Flights to Chicago - our lowest fares in points
From | To | Fare Type | Departure | Price |
|---|---|---|---|---|
| FromToronto (YYZ) | ToChicago (ORD) | One-way / Economy | Oct 11, 2025 | 12,000 pts + CAD 328 Viewed: 1 day ago |
| FromOttawa, ON (YOW) | ToChicago (ORD) | One-way / Economy | Mar 13, 2025 | 20,000 pts + CAD 312 Viewed: 1 day 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.