Book Air Canada flights to Chicago (ORD) from CAD 283*
*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)Montréal (YUL)to
Chicago (ORD)Montréal (YUL)to
Chicago (ORD)Vancouver (YVR)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Calgary (YYC)to
Chicago (ORD)Québec (YQB)to
Chicago (ORD)Québec (YQB)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)Halifax (YHZ)to
Chicago (ORD)Halifax (YHZ)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Toronto (YTZ)to
Chicago (ORD)Kelowna (YLW)to
Chicago (ORD)Kelowna (YLW)to
Chicago (ORD)
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 | Jan 22, 2027 | From 10,000 pts + CAD 166 Viewed: 13 hours ago |
| Montréal (YUL) | Chicago (ORD) | One-way / Economy | Sep 28, 2027 | From 22,024 pts + CAD 305 Viewed: 1 day ago |
| Vancouver (YVR) | Chicago (ORD) | One-way / Economy | Sep 19, 2027 | From 18,557 pts + CAD 175 Viewed: 15 hours ago |
| Calgary (YYC) | Chicago (ORD) | One-way / Economy | Feb 21, 2027 | From 81,420 pts + CAD 512 Viewed: 1 day ago |
| Taipei, Taiwan, China (TPE) | Chicago (ORD) | Round-trip / Economy | Aug 07, 2027 - Sep 24, 2027 | From 130,000 pts + CAD 281 Viewed: 1 day ago |
| Punta Cana (PUJ) | Chicago (ORD) | One-way / Economy | Feb 13, 2027 | From 22,500 pts + CAD 199 Viewed: 1 day ago |
| Liberia, Costa Rica (LIR) | Chicago (ORD) | One-way / Economy | Feb 25, 2027 | From 17,500 pts + CAD 161 Viewed: 1 day ago |