Class A Truck Driver Job in Chicago, IL – Windy Transportation

YOUR ROAD. YOUR RULES. Join Windy Transportation as a Class A Truck Driver in Chicago, Illinois. Whether you're an experienced professional or returning to the road, our lease-to-own program offers you 75% of every load revenue with zero upfront costs and no hidden fees. Why Choose Windy Transportation? 75% of Load Revenue – Earn real money directly, no middlemen involved $0 Down Lease – Drive brand-new 2026 trucks with no upfront payment No Balloon Payments – Own your truck without surprise financial terms Fuel Coverage – Up to 250 gallons per day at Love’s, Pilot, and TA locations Weekly Pay + Huge Load Board – Keep earning consistently with plenty of load options 24/7 Dispatch Support – Real people ready to assist you anytime Top-Tier Trucks Ready for the Road Freightliner Cascadia Kenworth T680 Volvo 760/660 Peterbilt 579 International ProStar All trucks are late-model, road-ready, and built for performance. Flexibility That Puts You First No Forced Dispatch – Choose your routes and destinations Pet Friendly – Bring pets of any breed and size along SAP-Friendly – We welcome drivers with second chances You Control Home Time – Manage your schedule and priorities Trailer Rental/Lease – Options from 2015 to 2026 models to fit your needs Compensation: Earn $3,000 per week as a full-time Class A Truck Driver. Location: Chicago, Illinois, United States Apply today to drive with Windy Transportation and take control of your career!