Book Air Canada flights to Chicago (ORD) from CAD 161*
*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)Frankfurt (FRA)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Punta Cana (PUJ)to
Chicago (ORD)Punta Cana (PUJ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Victoria (YYJ)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 | Apr 03, 2026 | From 6,000 pts + CAD 167 Viewed: 1 day ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Apr 03, 2026 | From 8,100 pts + CAD 173 Viewed: 1 day ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Aug 01, 2026 | From 11,600 pts + CAD 149 Viewed: 18 hours ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Jun 04, 2026 | From 8,500 pts + CAD 162 Viewed: 6 hours ago |
| Shanghai (PVG) | Chicago (ORD) | Round-trip / Economy | May 18, 2026 - May 31, 2026 | From 89,600 pts + CAD 243 Viewed: 1 day ago |
| Barcelona (BCN) | Chicago (ORD) | Round-trip / Economy | Jun 16, 2026 - Sep 15, 2026 | From 157,200 pts + CAD 286 Viewed: 1 day ago |
| San José, Costa Rica (SJO) | Chicago (ORD) | One-way / Economy | Apr 07, 2026 | From 12,500 pts + CAD 156 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.