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)Ottawa, ON (YOW)to
Chicago (ORD)Ottawa, ON (YOW)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Winnipeg (YWG)to
Chicago (ORD)Edmonton (YEG)to
Chicago (ORD)Edmonton (YEG)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.
Exclusive hotel deals for Aeroplan Members
Aeroplan HotelSavers saves you up to 30% in points at select partner hotels around the world. Look for the red HotelSavers tag to find your next dream stay.
Flights to Chicago - our lowest fares in points
From | To | Fare Type | Departure | Price |
|---|---|---|---|---|
| Toronto (YYZ) | Chicago (ORD) | One-way / Economy | Oct 04, 2026 | From 6,000 pts + CAD 166 Viewed: 9 hours ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Oct 18, 2026 | From 9,200 pts + CAD 125 Viewed: 1 day ago |
| Athens (ATH) | Chicago (ORD) | Round-trip / Economy | Apr 16, 2026 - Apr 26, 2026 | From 158,000 pts + CAD 597 Viewed: 1 day ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Aug 02, 2026 | From 9,300 pts + CAD 162 Viewed: 15 hours ago |
| Punta Cana (PUJ) | Chicago (ORD) | One-way / Economy | Mar 28, 2026 | From 12,500 pts + CAD 187 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.