Class A Truck Driver in Chicago, IL
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, IL
$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 costs or balloon payments.
Compensation and lease-to-own benefits
- Pay: $3,000 per week
- Receive 75% of load revenue
- $0 down lease options, including 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
Trucks and equipment
Drive late-model, road-ready equipment, including Freightliner Cascadia, Kenworth T680, Volvo 760 or 660, Peterbilt 579, and International ProStar trucks. Trailer rental or lease options are available, with models from 2015 through 2026.
Driver flexibility and support
- No forced dispatch; choose where you run
- 24/7 dispatch support from real people
- Control your home time and schedule
- Pet-friendly, with pets of every breed and size welcome
- SAP-friendly opportunity
Location and employment
This is a full-time, non-remote truck driving position based in Chicago, Illinois. Join Windy Transportation and explore a lease-to-own program designed to give drivers control over their routes, equipment, and home time.
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.