Explore Air Canada flights from Chicago to Canada from USD 101*
arrow_drop_down
arrow_drop_down
1 Passenger
arrow_drop_downPromotion code
arrow_drop_downtoday
today
*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.
Best fares between Chicago and Canada
flight_takeoff
flight_land
USD
Chicago (ORD)to
Toronto (YYZ) Sep 18, 2026
From
USD 101
One-way
Economy
Chicago (ORD)to
Toronto (YYZ) Sep 27, 2026
From
USD 101
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Jun 30, 2027
From
USD 219
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Jul 06, 2027
From
USD 219
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Nov 27, 2026
From
USD 161
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Nov 28, 2026
From
USD 161
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Nov 28, 2026
From
USD 145
One-way
Economy
Chicago (ORD)to
Calgary (YYC) Nov 03, 2026
From
USD 145
One-way
Economy
Chicago (ORD)to
Québec (YQB) Mar 17, 2027
From
USD 219
One-way
Economy
Chicago (ORD)to
Québec (YQB) Aug 11, 2027
From
USD 219
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Sep 26, 2026
From
USD 101
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Sep 27, 2026
From
USD 101
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Sep 18, 2026
From
USD 209
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Sep 17, 2026
From
USD 209
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Sep 17, 2026
From
USD 306
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Sep 20, 2026
From
USD 306
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Oct 06, 2026
From
USD 305
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Oct 07, 2026
From
USD 305
One-way
Economy
Chicago (ORD)to
St. John’s, NL (YYT) Sep 02, 2026
From
USD 607
One-way
Economy
Chicago (ORD)to
St. John’s, NL (YYT) Sep 01, 2026
From
USD 607
One-way
Economy
*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.
Find low fares between Chicago and Canada
flight_takeoff
flight_land
USD
From | To | Fare Type | Departure | Price |
|---|---|---|---|---|
| Chicago (ORD) | Toronto (YYZ) | One-way / Economy | Nov 29, 2026 | From USD 158 Viewed: 22 hours ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | Jun 30, 2027 | From USD 219 Viewed: 22 hours ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Nov 27, 2026 | From USD 161 Viewed: 18 hours ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Dec 08, 2026 | From USD 145 Viewed: 14 hours ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | Jul 27, 2027 | From USD 219 Viewed: 1 day ago |
| Chicago (ORD) | Halifax (YHZ) | One-way / Economy | May 05, 2027 | From USD 215 Viewed: 14 hours ago |
| Chicago (ORD) | Ottawa, ON (YOW) | One-way / Economy | Nov 29, 2026 | From USD 364 Viewed: 22 hours ago |
| Chicago (ORD) | Edmonton (YEG) | One-way / Economy | Dec 08, 2026 | From USD 158 Viewed: 14 hours ago |
| Chicago (ORD) | Regina (YQR) | One-way / Economy | Jan 27, 2027 | From USD 221 Viewed: 1 day ago |
*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.