High-paying driving jobs in Winnipeg
Driving encompasses the operation of vehicles for transportation purposes. Drivers play a crucial role in ensuring safe and efficient travel for passengers and goods. They must possess various skills, including navigation, communication, and adherence to traffic laws.
The 143 driving jobs listed below pay well, with salaries between $39,116 and $160,497 per year. Truck Driver, Driver and Delivery Driver are among the most popular high-paying roles in Brampton, ON.
Job title
Updated Jul. 18, 2026
Job title
Winnipeg, MB
Manitoba
Job openings (Winnipeg)
Owner Operator Driver
Winnipeg
$160,497
per year
Manitoba
$170,137
per year
Long Haul Driver
Winnipeg
$72,742
per year
Manitoba
$74,314
per year
Truck Driver
Winnipeg
$24.88
per hour
Manitoba
$25.36
per hour
Bus Driver
Winnipeg
$24.84
per hour
Manitoba
$23.86
per hour
Driver
Winnipeg
$19.90
per hour
Manitoba
$19.91
per hour
Delivery Driver
Winnipeg
$18.83
per hour
Manitoba
$19.17
per hour
Shuttle Driver
Winnipeg
$16.94
per hour
Manitoba
$19.57
per hour
Job descriptions below are for educational purposes. Please refer to the employer's job description for complete details.
-
Owner Operator Driver
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Please refer to the employers job description for complete details.
Owner Operator Drivers manage their own transport business, complete long-haul deliveries, and maintain their vehicles. They need commercial driving expertise, familiarity with transport regulations, and strong time management skills to succeed independently.
See 11 jobsAverage salary
Winnipeg
$160,497 per yearManitoba
$170,137 per yearSkills
- Driving
- Tractor-trailer
- Commercial driving
-
Long Haul Driver
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Please refer to the employers job description for complete details.
Long Haul Drivers transport goods across long distances, manage delivery schedules, and maintain vehicle safety. They need commercial driving expertise, knowledge of transportation regulations, and strong time-management skills to handle extended routes reliably.
See 25 jobsAverage salary
Winnipeg
$72,742 per yearManitoba
$74,314 per yearSkills
- Time management
-
Truck Driver
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Please refer to the employers job description for complete details.
Truck Drivers transport goods safely, manage route navigation, and maintain vehicle condition. They need expertise in commercial driving, knowledge of transport regulations, and strong time-management skills to ensure timely, compliant deliveries across Canada.
See 57 jobsAverage salary
Winnipeg
$24.88 per hourManitoba
$25.36 per hourSkills
- Driving
- Load & unload
- Bus driving
- Commercial driving
-
Bus Driver
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Please refer to the employers job description for complete details.
Bus Drivers operate passenger buses safely, follow scheduled routes, and maintain clear communication with riders. They need a valid commercial driverβs licence, familiarity with local regulations, and strong spatial awareness to adapt to traffic conditions.
See 6 jobsAverage salary
Winnipeg
$24.84 per hourManitoba
$23.86 per hourSkills
- Driving
- Forklift
- Load & unload
- Automotive repair
-
Driver
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Please refer to the employers job description for complete details.
Drivers transport passengers or goods safely, navigate routes, and maintain vehicle condition per regulations. They need valid licences, knowledge of traffic laws, and strong time-management skills to meet delivery or schedule demands efficiently.
See 16 jobsAverage salary
Winnipeg
$19.90 per hourManitoba
$19.91 per hourSkills
- Driving
- Load & unload
- Bus driving
- Automotive repair
-
Delivery Driver
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Please refer to the employers job description for complete details.
Delivery Drivers transport goods efficiently, navigate routes safely, and manage timely deliveries to customers. They need valid licenses, proficiency with GPS tools, and strong customer service skills to succeed in fast-paced settings.
See 24 jobsAverage salary
Winnipeg
$18.83 per hourManitoba
$19.17 per hourSkills
- Driving
- Load & unload
- Bus driving
- English
-
Shuttle Driver
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Please refer to the employers job description for complete details.
Shuttle Drivers transport passengers safely between locations, manage schedules, and maintain vehicle cleanliness. They need a valid driverβs licence, navigation skills, and the ability to assist diverse passengers with courtesy and care.
See 4 jobsAverage salary
Winnipeg
$16.94 per hourManitoba
$19.57 per hourSkills
- Driving
- English
- Communication skills
- Customer service
- Shuttle driving