Chicago is a major economic center with strong demand across finance, logistics, tech, and healthcare. Companies such as United Airlines, Boeing, McDonald’s, and Stripe have deep roots in the city. Jobs in Chicago benefit from a lower cost of living than coastal hubs while still offering access to world-class employers.
Drive your career forward with our dedicated job board for driving-based roles across the UK. Whether you're an experienced driver or looking to enter the profession, our platform offers a wide range of opportunities in logistics, delivery, public transport, and more. Stay ahead of the competition with our up-to-date listings from reputable employers seeking skilled drivers. Explore diverse positions that match your qualifications and preferences. Begin your search today and accelerate your career in the driving sector with our comprehensive job offerings.
156 jobs for Highway Driver Leasing in Chicago
Hiring Regional Midwest Flatbed Drivers, Experienced or Ready to Learn. Now Hiring Regional Midwest Flatbed Drivers – Experienced or Ready to Learn! Looking for a career where you can grow your skills, earn top pay, and still be home on weekends? At Decker Truck Line, we're hiring regional flatbed drivers and will train motivated drivers with at...
Hiring Regional Midwest Flatbed Drivers, Experienced or Ready to Learn. Now Hiring Regional Midwest Flatbed Drivers – Experienced or Ready to Learn! Looking for a career where you can grow your skills, earn top pay, and still be home on weekends? At Decker Truck Line, we're hiring regional flatbed drivers and will train motivated drivers with at...
Flatbed Class A CDL OTR Driver: Earn $1,094.00 – $2,103.53 per week. Full Benefits
NewPosted 16 May 2026System TransportCDL A OTR Flatbed Driver: $1,094.00 – $2,103.53 per week. Full Benefits AMERICA PROUD. FLATBED STRONG. DRIVE SYSTEM TRANSPORT! Looking for an exciting driving opportunity in the western region of America? System Transport is hiring experienced CDL-A flatbed truck drivers for regional and OTR routes. As a driver, you will be transporting important g...
OTR & Regional CDL-A Tanker Drivers! CORE48 Transport, LLC is a bold, new name in trucking - we're rebranding what it means to drive with a company that truly cares. As a third-generation transportation leader, we honor nearly 60 years of excellence with a fresh, driver-first approach to Tanker, Reefer, and Dry Van freight. We offer top-notch bene...
CDL-A Linehaul Truck Driver, Full-time. Job Description Road Drivers are responsible for the pickup and delivery of cargo trailers to and from various long-distance destinations. Responsibilities Performing various tasks ranging from check-in, tractor/trailer inspection, tractor set up and the pickup and delivery of cargo. Actual duties and sched...
Hiring Regional Midwest Flatbed Drivers, Experienced or Ready to Learn. Now Hiring Regional Midwest Flatbed Drivers – Experienced or Ready to Learn! Looking for a career where you can grow your skills, earn top pay, and still be home on weekends? At Decker Truck Line, we're hiring regional flatbed drivers and will train motivated drivers with at...
Flatbed CDL-A OTR Driver: Earn $1,094.00 – $2,103.53 per week. Full Benefits
NewPosted 21 May 2026System TransportCDL A OTR Flatbed Driver: $1,094.00 – $2,103.53 per week. Full Benefits AMERICA PROUD. FLATBED STRONG. DRIVE SYSTEM TRANSPORT! Looking for an exciting driving opportunity in the western region of America? System Transport is hiring experienced CDL-A flatbed truck drivers for regional and OTR routes. As a driver, you will be transporting important g...
Class A CDL Flatbed OTR Driver: Earn $1,094.00 – $2,103.53 per week. Full Benefits
NewPosted 16 May 2026System TransportCDL A OTR Flatbed Driver: $1,094.00 – $2,103.53 per week. Full Benefits AMERICA PROUD. FLATBED STRONG. DRIVE SYSTEM TRANSPORT! Looking for an exciting driving opportunity in the western region of America? System Transport is hiring experienced CDL-A flatbed truck drivers for regional and OTR routes. As a driver, you will be transporting important g...
CDL-A OTR Flatbed Driver: Earn $1,094.00 – $2,103.53 per week. Full Benefits
NewPosted 16 May 2026System TransportCDL A OTR Flatbed Driver: $1,094.00 – $2,103.53 per week. Full Benefits AMERICA PROUD. FLATBED STRONG. DRIVE SYSTEM TRANSPORT! Looking for an exciting driving opportunity in the western region of America? System Transport is hiring experienced CDL-A flatbed truck drivers for regional and OTR routes. As a driver, you will be transporting important g...
CDL-A Linehaul Truck Driver, Full-time. Job Description Road Drivers are responsible for the pickup and delivery of cargo trailers to and from various long-distance destinations. Responsibilities Performing various tasks ranging from check-in, tractor/trailer inspection, tractor set up and the pickup and delivery of cargo. Actual duties and sched...
Jobs in Chicago center on finance, manufacturing, food processing, and a rapidly growing tech sector. Boeing, United Airlines, Abbott Laboratories, JPMorgan Chase, and Northwestern Medicine are major employers. Salaries are competitive nationally while the cost of living sits well below New York or San Francisco, making it an attractive market for professionals. The CTA "L" train and Metra commuter rail form one of the country's best public transit networks. Key employment districts include the Loop, River North, Fulton Market, and the growing West Loop tech hub. Chicago is also a major logistics center thanks to O'Hare Airport and its central rail connections.