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 76 driving jobs listed below pay well, with salaries between $35,200 and $172,939 per year. Driver, Truck Driver and Delivery Driver are among the most popular high-paying roles in Windsor, ON.

Job title

Updated Nov. 06, 2026
Job title
Windsor, ON
Ontario
Job openings (Windsor)

Owner Operator Driver

Windsor

$172,939 per year

Ontario

$140,724 per year

Driver

Windsor

$2,405 per week

Ontario

$1,440 per week

Long Haul Driver

Windsor

$32.29 per hour

Ontario

$33.92 per hour

Truck Driver

Windsor

$27.47 per hour

Ontario

$29.57 per hour

Transport Driver

Windsor

$24.46 per hour

Ontario

$28.42 per hour

Courier

Windsor

$21.17 per hour

Ontario

$22.29 per hour

Delivery Driver

Windsor

$20.25 per hour

Ontario

$21.85 per hour

Shuttle Driver

Windsor

$18.49 per hour

Ontario

$19.64 per hour

Job descriptions below are for educational purposes. Please refer to the employer's job description for complete details.