High-paying driving jobs in Windsor
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 75 driving jobs listed below pay well, with salaries between $35,200 and $174,910 per year. Delivery Driver, Driver and Truck Driver are among the most popular high-paying roles in Windsor, ON.
Job title
Updated Oct. 17, 2026
Job title
Windsor, ON
Ontario
Job openings (Windsor)
Owner Operator Driver
Windsor
$174,910
per year
Ontario
$139,684
per year
Driver
Windsor
$2,406
per week
Ontario
$1,435
per week
Truck Driver
Windsor
$27.31
per hour
Ontario
$29.66
per hour
Courier
Windsor
$21.25
per hour
Ontario
$22.31
per hour
Delivery Driver
Windsor
$20.28
per hour
Ontario
$22.04
per hour
Job descriptions below are for educational purposes. Please refer to the employer's job description for complete details.
-
Owner Operator Driver
Review job description
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 7 jobsAverage salary
Windsor
$174,910 per yearOntario
$139,684 per yearSkills
- Driving
- Tractor-trailer
- Commercial driving
-
Driver
Review job description
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 21 jobsAverage salary
Windsor
$2,406 per weekOntario
$1,435 per weekSkills
- Driving
- Load & unload
- Bus driving
- Automotive repair
-
Truck Driver
Review job description
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 19 jobsAverage salary
Windsor
$27.31 per hourOntario
$29.66 per hourSkills
- Driving
- Load & unload
- Bus driving
- Commercial driving
-
Courier
Review job description
Please refer to the employers job description for complete details.
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 5 jobsAverage salary
Windsor
$21.25 per hourOntario
$22.31 per hourSkills
- Driving
- Communication skills
- Customer service
- Heavy lifting
-
Delivery Driver
Review job description
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 23 jobsAverage salary
Windsor
$20.28 per hourOntario
$22.04 per hourSkills
- Driving
- Load & unload
- Bus driving
- English