Book Air Canada flights to Chicago (ORD) from CAD 168*
*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)Vancouver (YVR)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Montréal (YUL)to
Chicago (ORD)Montréal (YUL)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)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)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)St. John’s, NL (YYT)to
Chicago (ORD)St. John’s, NL (YYT)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 |
|---|---|---|---|---|
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Aug 21, 2026 | From 50,000 pts + CAD 467 Viewed: 1 day ago |
| Hong Kong SAR, China (HKG) | Chicago (ORD) | Round-trip / Economy | Sep 16, 2026 - Oct 21, 2026 | From 100,500 pts + CAD 306 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Aug 24, 2026 | From 19,200 pts + CAD 324 Viewed: 1 day ago |
| Taipei, Taiwan, China (TPE) | Chicago (ORD) | Round-trip / Economy | Apr 07, 2026 - Apr 30, 2026 | From 100,000 pts + CAD 157 Viewed: 1 day ago |
| Liberia, Costa Rica (LIR) | Chicago (ORD) | One-way / Economy | Apr 22, 2026 | From 15,000 pts + CAD 155 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.