Explore Air Canada flights from Chicago to Canada from USD 95*
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) Jul 20, 2026
From
USD 95
One-way
Economy
Chicago (ORD)to
Toronto (YYZ) Jul 21, 2026
From
USD 95
One-way
Economy
Chicago (ORD)to
Montréal (YUL) Apr 22, 2026
From
USD 150
One-way
Economy
Chicago (ORD)to
Montréal (YUL) May 08, 2026
From
USD 150
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Apr 21, 2026
From
USD 213
One-way
Economy
Chicago (ORD)to
Vancouver (YVR) Jun 29, 2026
From
USD 213
One-way
Economy
Chicago (ORD)to
Calgary (YYC) May 12, 2026
From
USD 112
One-way
Economy
Chicago (ORD)to
Calgary (YYC) May 02, 2026
From
USD 116
One-way
Economy
Chicago (ORD)to
Québec (YQB) May 05, 2026
From
USD 229
One-way
Economy
Chicago (ORD)to
Québec (YQB) May 07, 2026
From
USD 229
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Apr 29, 2026
From
USD 277
One-way
Economy
Chicago (ORD)to
Halifax (YHZ) Apr 28, 2026
From
USD 277
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Jul 04, 2026
From
USD 316
One-way
Economy
Chicago (ORD)to
Winnipeg (YWG) Jul 09, 2026
From
USD 316
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) May 09, 2026
From
USD 164
One-way
Economy
Chicago (ORD)to
Edmonton (YEG) Jun 06, 2026
From
USD 164
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Jul 17, 2026
From
USD 95
One-way
Economy
Chicago (ORD)to
Toronto (YTZ) Jul 12, 2026
From
USD 95
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Jun 13, 2026
From
USD 254
One-way
Economy
Chicago (ORD)to
Ottawa, ON (YOW) Jun 14, 2026
From
USD 254
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 | Jul 18, 2026 | From USD 95 Viewed: 1 day ago |
| Chicago (ORD) | Montréal (YUL) | One-way / Economy | Sep 28, 2026 | From USD 162 Viewed: 6 hours ago |
| Chicago (ORD) | Vancouver (YVR) | One-way / Economy | Jul 30, 2026 | From USD 213 Viewed: 1 day ago |
| Chicago (ORD) | Calgary (YYC) | One-way / Economy | Oct 10, 2026 | From USD 134 Viewed: 18 hours ago |
| Chicago (ORD) | Ottawa, ON (YOW) | One-way / Economy | Jul 13, 2026 | From USD 307 Viewed: 10 hours ago |
| Chicago (ORD) | Québec (YQB) | One-way / Economy | Sep 05, 2026 | From USD 255 Viewed: 22 hours ago |
| Chicago (ORD) | Halifax (YHZ) | One-way / Economy | Jul 08, 2026 | From USD 328 Viewed: 18 hours ago |
| Chicago (ORD) | Winnipeg (YWG) | One-way / Economy | Jul 09, 2026 | From USD 316 Viewed: 10 hours ago |
| Chicago (ORD) | Edmonton (YEG) | One-way / Economy | Sep 05, 2026 | From USD 186 Viewed: 14 hours ago |
| Chicago (ORD) | Toronto (YTZ) | One-way / Economy | Jul 14, 2026 | From USD 95 Viewed: 1 day ago |
| Chicago (ORD) | Regina (YQR) | One-way / Economy | Aug 28, 2026 | From USD 229 Viewed: 8 hours ago |
| Chicago (ORD) | Sudbury (YSB) | One-way / Economy | Jul 09, 2026 | From USD 306 Viewed: 12 hours ago |
| Chicago (ORD) | Deer Lake (YDF) | One-way / Economy | Aug 08, 2026 | From USD 281 Viewed: 11 hours 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.