Class A Truck Driver in Chicago, Illinois
Published on CazVidat Windy Transportation
YOUR ROAD. YOUR RULES. Whether you're a seasoned pro or getting back on track, our lease-to-own program puts 75% of every load straight into your pocket —
Salary
$3,000 per week
Location
Chicago, Illinois, United States
Employment type
Full time
Workplace
Not provided
Class A Truck Driver in Chicago, Illinois
$3,000 per week
Job description
Windy Transportation is hiring a full-time Class A Truck Driver in Chicago, Illinois. This lease-to-own opportunity offers drivers 75% of load revenue, weekly pay, and no upfront lease costs. Drivers choose where they run, manage their home time, and receive 24/7 dispatch support.
Pay and Lease-to-Own Benefits
- Pay: $3,000 per week
- Receive 75% of load revenue
- $0 down lease options, including on new 2026 trucks
- No balloon payments
- Fuel coverage of up to 250 gallons per day at Love’s, Pilot, and TA
- Weekly pay and access to a large load board
- 24/7 dispatch support from real people
Equipment
Drive late-model, road-ready trucks, including Freightliner Cascadia, Kenworth T680, Volvo 760 or 660, Peterbilt 579, and International ProStar models.
Driver Flexibility
- No forced dispatch; choose where you run
- Control your home-time schedule
- Pet-friendly, with pets of every breed and size welcome
- SAP-friendly opportunity
- Trailer rental or lease options, with models from 2015–2026
Apply to explore the Class A Truck Driver lease-to-own opportunity with Windy Transportation in Chicago.
Frequently asked questions
How much does this Class A Truck Driver job pay?
This position pays USD 3,000 per week as a full-time Class A Truck Driver.
Is this job based in Chicago or remote?
This is an on-site position based in Chicago, Illinois.
What kind of trucks will I be driving?
You will drive brand-new 2026 trucks including Freightliner Cascadia, Kenworth T680, Volvo 760/660, Peterbilt 579, and International ProStar models.
Do I have to accept assigned routes or can I choose my own?
There is no forced dispatch, so you can choose your routes and destinations.
Are there any upfront costs to lease a truck?
No, the lease-to-own program requires zero upfront payment and has no hidden fees or balloon payments.
What kind of support will I have while on the road?
You will have 24/7 dispatch support with real people ready to assist you anytime.