Oakville, On Driver (independent contractor) Jobs – 6 Openings This Week

Care Driver – Student Transportation (Independent Contractor)
VIPS RIDE —Burlington, ON
- $70–$140 a day
- Temporary
- Driving
- Flexible schedule
Quick apply
Owner operator Delivery Driver
SK Courier Service Inc. —Mississauga, ON
- $150–$250 a day
- Full-time
- English
- High school diploma or GED
Quick apply
OTR B-Train Solo AZ Driver (Independent Contractor)
Samee Metals Trading —Hamilton, ON
- From $127,400 a year
- Full-time
- Driving
- In-person
- OTR
Quick apply
DZ Driver - Local P&D - $25.76 - $26.64/Hr
Nova Driver Services —Oakville, ON
- $25.76 an hour
- Full-time
- Heavy lifting
- Customer service
- English
- Dental care
- Paid time off
Quick apply
5d
Independent Moving Contractors – Furniture/Clothing Donation & Delivery
Prep'n Sell —Mississauga, ON
- $84–$85 an hour
- English
- Driving
Quick apply
8d
OTR Flatbed Solo Driver (AZ)-Independent Contractor
Samee Metal Trading —Hamilton, ON
- From $100,000 a year
- Full-time
- Driving
- In-person
- Commercial driving
Quick apply

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Owner Operator Delivery Driver
Ripple Logistics —Scarborough, ON
Valid vehicle insurance and registration. Successful candidates will be responsible for delivering parcels throughout *Downtown Toronto* while providing…
$290 a day
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Owner Operator Truck Driver - US CROSS BORDER SHORT/LONG RUNS
Tenaxx Logistics —Mississauga, ON
Valid commercial driver’s license (CDL) with a clean driving record. Conduct pre-trip and post-trip inspections of the vehicle to ensure it is in safe operating…
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Owner Operator Delivery Driver
Ripple Logistics —Scarborough, ON
Valid vehicle insurance and registration. Successful candidates will be responsible for delivering parcels throughout *Downtown Toronto* while providing…
$290 a day
Quick apply
DZ Truck Driver
RONA Port Hope, Northumberland Building Materials —Port Hope, ON
Must possess a valid Ontario Class DZ (or higher) drivers’ licence. While not on the road, the DZ Truck Driver builds orders, loads customers’ vehicles, and…
$23–$25 an hour
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driver (independent contractor) jobs near oakville, on

Care Driver – Student Transportation (Independent Contractor)

VIPS RIDE
Burlington, ON

Quick apply

Job details

Temporary | Part-time | Full-time | Fixed term contract
$70–$140 a day

Qualifications

Driving
Driving Licence

Full job description

Care Driver – Student Transportation (Independent Contractor)

Company: VIPS RIDE / First Alt
Location: Burlington, and nearby Ontario cities
Start Date: January 22, 2026
Estimated Pay: CAD $70–$140 per day

✅ About the Role

VIPS RIDE is hiring independent drivers to safely transport students to and from school. This is a contract position, perfect for reliable, caring, and punctual drivers looking for flexible and meaningful work during the school year.

As a Care Driver, you’ll play an important role in your community — helping students get to school safely and on time while maintaining a consistent weekday schedule.

✅ Pricing for Rides

Trip Minimum: CAD $40.00 (for 1–25 km)
CAD $1.10 per km for the portion between 25–40 km
CAD $1.00 per km for any distance beyond 40 km
A CAD $5.00 dispatch/service fee is deducted per ride.

Drivers net CAD $35.00 per ride for trips up to 25 km.
Longer trips earn more based on total distance.

Drivers are paid per trip, not per student.

✅ Vehicle Requirements

A sedan, SUV, or mini passenger van
Vehicle must be 10 years old or newer (2016 or newer)
Valid vehicle registration and insurance required
Must pass a vehicle safety inspection
Can be done at any mechanic or Canadian Tire location
No government-issued inspection required

✅ Driver Requirements

21 years or older
Valid Ontario driver’s licence
Clear driver abstract (no major violations or DUIs)
Photo ID (passport or government-issued) with picture, name, and date of birth
Must complete a background check and onboarding process

✅ Onboarding Process

Submit documents (driver’s licence, passport/ID, insurance, registration)
Complete a background check (we’ll guide you through it)
Watch short online safety training videos
Pass a vehicle inspection
Download and activate the First Alt Driver App

✅ Why Drive with VIPS RIDE?

Be your own boss – independent contractor position
Consistent Monday to Friday school-year schedule
Competitive and reliable pay
Flexible hours (morning and afternoon)
Supportive operations and onboarding team
Make a difference transporting students safely every day

Hiring Areas Across Ontario

Brampton
Mississauga
Toronto
Etobicoke
North York
Scarborough
Vaughan
Markham
Richmond Hill
Oakville
Burlington
Milton
Ajax
Pickering
Whitby
Oshawa

(and surrounding Greater Toronto Area regions)

✅ How to Apply

Text: (206) 397-2334
Call: (833) 847-4968

Please include in your message:

Full Name
City you’re applying from
Email Address & Phone Number
Vehicle year & model

✅ Screening Questions

Are you located in or near one of the Ontario cities listed above?
Do you have access to a vehicle (2016 or newer)?
Are you available 7:00–9:00 AM and 2:00–4:00 PM, Monday–Friday?
Do you have any major driving violations in the past 3 years?
Have you ever had a DUI?
Are you legally authorized to work in Canada?
Are you 21 years or older?

Job Types: Full-time, Part-time, Fixed term contract
Contract length: 10 months

Pay: $70.00-$140.00 per day

Work Location: On the road

Quick apply

Refine Your Search

driver (independent contractor) jobs in oakville, on

Care Driver – Student Transportation (Independent Contractor)

Owner operator Delivery Driver

OTR B-Train Solo AZ Driver (Independent Contractor)

DZ Driver - Local P&D - $25.76 - $26.64/Hr

Independent Moving Contractors – Furniture/Clothing Donation & Delivery

OTR Flatbed Solo Driver (AZ)-Independent Contractor

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