Class A Truck Driver

At Windy Transportation, a leading logistics company based in Chicago, Illinois, we're committed to empowering professional truck drivers with opportunities for career growth and financial success. Whether you're an experienced Class A Truck Driver or returning to the road, our innovative lease-to-own program offers you the chance to earn 75% of every load's revenue directly, with no upfront costs or hidden fees. Join our team on-site in Chicago and take control of your driving career with top-tier equipment, flexible schedules, and comprehensive support designed to put you first. Key Responsibilities Operate Class A commercial trucks safely and efficiently across regional and national routes, ensuring timely delivery of freight. Maintain compliance with all federal, state, and local transportation regulations, including Hours of Service (HOS) and safety protocols. Manage load documentation accurately, including bills of lading, delivery receipts, and inspection reports. Communicate effectively with dispatch and customers to coordinate schedules and resolve issues promptly. Perform pre-trip, en-route, and post-trip vehicle inspections to ensure roadworthiness and report any mechanical issues immediately. Maximize revenue by utilizing our extensive load board and selecting routes that fit your preferences and schedule. Adhere to company policies regarding fuel usage, leveraging our fuel coverage benefit of up to 250 gallons per day at major truck stops. Contribute to a positive team environment by supporting 24/7 dispatch and maintenance teams when needed. What We're Looking For Required: Valid Class A Commercial Driver’s License (CDL) with a clean driving record. Minimum of 1 year of professional truck driving experience preferred. Strong knowledge of DOT regulations and safety standards. Ability to manage time effectively and work independently. Excellent communication and problem-solving skills. Preferred: Experience with lease-to-own truck programs or fleet management. Familiarity with Freightliner Cascadia, Kenworth T680, Volvo 760/660, Peterbilt 579, or International ProStar trucks. Pet-friendly drivers who appreciate our flexible home time policies. Applicants with SAP (Second Chance) eligibility, welcoming those seeking career advancement. What We Offer Competitive weekly pay averaging $3,000 per week, with 75% of load revenue directly to you. $0 down lease-to-own program on brand-new 2026 trucks with no balloon payments. Fuel coverage up to 250 gallons per day at Love’s, Pilot, and TA truck stops. 24/7 dispatch support staffed by real people ready to assist anytime. Flexible scheduling with no forced dispatch and control over your home time. Pet-friendly policy allowing you to bring your pets on the road. Access to a large load board to keep you rolling and earning consistently. Professional development opportunities to grow your career in trucking and logistics. Frequently Asked Questions What is the average weekly pay for this Class A Truck Driver position? The average pay is approximately $3,000 per week, with drivers earning 75% of every load's revenue. Do I need prior experience to apply? While 1 year of professional truck driving experience is preferred, we welcome drivers returning to the industry and offer support through our lease-to-own program. Are the trucks provided new? Yes, we offer brand-new 2026 trucks as part of our lease-to-own program, including models like Freightliner Cascadia and Kenworth T680. Is this position on-site or remote? This is an on-site position based in Chicago, Illinois. Drivers operate trucks on regional and national routes. What kind of support does Windy Transportation provide? We offer 24/7 dispatch support, fuel coverage, and flexible scheduling to ensure drivers have the resources they need to succeed. Can I bring my pet with me? Yes, our pet-friendly policy welcomes all pets regardless of breed or size. For more information about trucking careers and industry standards, visit