Book Air Canada flights to Chicago (ORD) from CAD 163*
*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)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)St. John’s, NL (YYT)to
Chicago (ORD)St. John’s, NL (YYT)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Winnipeg (YWG)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 | Jun 28, 2026 | From 8,600 pts + CAD 120 Viewed: 17 hours ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Oct 09, 2026 | From 9,200 pts + CAD 125 Viewed: 6 hours ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Mar 29, 2026 | From 12,500 pts + CAD 102 Viewed: 15 hours ago |
| Taipei, Taiwan, China (TPE) | Chicago (ORD) | Round-trip / Economy | Apr 14, 2026 - Jul 13, 2026 | From 100,000 pts + CAD 158 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Jun 24, 2026 | From 9,800 pts + CAD 121 Viewed: 7 hours ago |
| Québec (YQB) | Chicago (ORD) | One-way / Economy | Sep 20, 2026 | From 10,100 pts + CAD 125 Viewed: 1 day ago |
| Toronto (YTZ) | Chicago (ORD) | One-way / Economy | Jul 05, 2026 | From 32,800 pts + CAD 443 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.