Book Air Canada flights to Chicago (ORD) from CAD 154*
Flights to Chicago - our lowest fares in cash
Toronto (YYZ)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Montréal (YUL)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Saskatoon (YXE)to
Chicago (ORD)Victoria (YYJ)to
Chicago (ORD)Kelowna (YLW)to
Chicago (ORD)St. John’s, NL (YYT)to
Chicago (ORD)Moncton (YQM)to
Chicago (ORD)Tel Aviv (TLV)to
Chicago (ORD)Regina (YQR)to
Chicago (ORD)London, ON (YXU)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 | Jun 29, 2025 | 16,700 pts + CAD 118 Viewed: 1 day ago |
| FromVancouver (YVR) | ToChicago (ORD) | One-way / Economy | Dec 10, 2025 | 17,300 pts + CAD 110 Viewed: 17 hours ago |
| FromEdmonton (YEG) | ToChicago (ORD) | One-way / Economy | Oct 10, 2025 | 22,600 pts + CAD 338 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.