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 275 driving jobs listed below pay well, with salaries between $32,870 and $159,569 per year. Truck Driver, Delivery Driver and Driver are among the most popular high-paying roles in Winnipeg, MB.
Job title
Updated Oct. 17, 2026
Job title
Winnipeg, MB
Manitoba
Job openings (Winnipeg)
Owner Operator Driver
Winnipeg
$159,569
per year
Manitoba
$171,055
per year
Delivery Person (independent Contractor)
Winnipeg
$30.60
per hour
Manitoba
$30.61
per hour
Long Haul Driver
Winnipeg
$29.82
per hour
Manitoba
$29.97
per hour
Truck Driver
Winnipeg
$26.39
per hour
Manitoba
$26.54
per hour
Bus Driver
Winnipeg
$24.50
per hour
Manitoba
$24.63
per hour
Snow Plow Operator
Winnipeg
$23.65
per hour
Manitoba
$23.49
per hour
Courier
Winnipeg
$22.34
per hour
Manitoba
$20.67
per hour
Driver
Winnipeg
$19.84
per hour
Manitoba
$20.22
per hour
Delivery Driver
Winnipeg
$18.29
per hour
Manitoba
$18.54
per hour
Shuttle Driver
Winnipeg
$17.62
per hour
Manitoba
$17.87
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 22 jobsAverage salary
Winnipeg
$159,569 per yearManitoba
$171,055 per yearSkills
- Driving
- Tractor-trailer
- Commercial driving
-
Delivery Person (independent Contractor)
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Please refer to the employers job description for complete details.
Delivery Persons coordinate pick-up and drop-off of goods, ensuring timely, safe transit as independent contractors. They need navigation proficiency, customer communication skills, and valid vehicle licensing for efficient urban delivery service.
See 23 jobsAverage salary
Winnipeg
$30.60 per hourManitoba
$30.61 per hour -
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 26 jobsAverage salary
Winnipeg
$29.82 per hourManitoba
$29.97 per hourSkills
- 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 70 jobsAverage salary
Winnipeg
$26.39 per hourManitoba
$26.54 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 driver’s licence, familiarity with local regulations, and strong spatial awareness to adapt to traffic conditions.
See 11 jobsAverage salary
Winnipeg
$24.50 per hourManitoba
$24.63 per hourSkills
- Driving
- Forklift
- Load & unload
- Automotive repair
-
Snow Plow Operator
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Please refer to the employers job description for complete details.
Snow Plow Operators clear snow and ice from roads, operate heavy equipment safely in winter conditions, and maintain visibility using de-icing materials. They need expertise in vehicle control, road safety standards, and time-sensitive task management.
See 10 jobsAverage salary
Winnipeg
$23.65 per hourManitoba
$23.49 per hour -
Courier
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Couriers deliver packages quickly and safely across varied locations, manage delivery routes efficiently, and handle shipping paperwork accurately. They need expertise in navigation, time management, and communication to succeed in fast-paced logistics.
See 8 jobsAverage salary
Winnipeg
$22.34 per hourManitoba
$20.67 per hourSkills
- Driving
- Communication skills
- Customer service
- Heavy lifting
-
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 49 jobsAverage salary
Winnipeg
$19.84 per hourManitoba
$20.22 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 51 jobsAverage salary
Winnipeg
$18.29 per hourManitoba
$18.54 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 driver’s licence, navigation skills, and the ability to assist diverse passengers with courtesy and care.
See 5 jobsAverage salary
Winnipeg
$17.62 per hourManitoba
$17.87 per hourSkills
- Driving
- English
- Communication skills
- Customer service
- Shuttle driving