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.
52 jobs for Highway Driver Leasing in Chicago
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...
CDL-A Truck Drivers: GREAT ROUTES AVAILABLE! Top Pay & Benefits OTR Drivers: Average 2,000+ miles per week. Bonuses may be available. Count on consistent miles and paycheck with flexible home time that works for you.Regional Opportunities: Drive regional and earn strong pay and dependable miles with the confidence of knowing you'll be home e...
CDL-A Truck Drivers: GREAT ROUTES AVAILABLE! Top Pay & Benefits OTR Drivers: Average 2,000+ miles per week. Bonuses may be available. Count on consistent miles and paycheck with flexible home time that works for you.Regional Opportunities: Drive regional and earn strong pay and dependable miles with the confidence of knowing you'll be home e...
CDL-A Truck Drivers: GREAT ROUTES AVAILABLE! Top Pay & Benefits OTR Drivers: Average 2,000+ miles per week. Bonuses may be available. Count on consistent miles and paycheck with flexible home time that works for you.Regional Opportunities: Drive regional and earn strong pay and dependable miles with the confidence of knowing you'll be home e...
CDL-A Truck Drivers: GREAT ROUTES AVAILABLE! Top Pay & Benefits OTR Drivers: Average 2,000+ miles per week. Bonuses may be available. Count on consistent miles and paycheck with flexible home time that works for you.Regional Opportunities: Drive regional and earn strong pay and dependable miles with the confidence of knowing you'll be home e...
CDL-A Truck Drivers: GREAT ROUTES AVAILABLE! Top Pay & Benefits OTR Drivers: Average 2,000+ miles per week. Bonuses may be available. Count on consistent miles and paycheck with flexible home time that works for you.Regional Opportunities: Drive regional and earn strong pay and dependable miles with the confidence of knowing you'll be home e...
CDL-A Truck Drivers: GREAT ROUTES AVAILABLE! Top Pay & Benefits OTR Drivers: Average 2,000+ miles per week. Bonuses may be available. Count on consistent miles and paycheck with flexible home time that works for you.Regional Opportunities: Drive regional and earn strong pay and dependable miles with the confidence of knowing you'll be home e...
CDL-A Truck Drivers: GREAT ROUTES AVAILABLE! Top Pay & Benefits OTR Drivers: Average 2,000+ miles per week. Bonuses may be available. Count on consistent miles and paycheck with flexible home time that works for you.Regional Opportunities: Drive regional and earn strong pay and dependable miles with the confidence of knowing you'll be home e...
CDL-A HAZMAT Tanker Driver - $.80 CPM loaded, $0.60 CPM empty
NewPosted 23 May 2026TransWood CarriersTerminals located in both Lansing, IL and Channahon, IL Rewarding Career Starts Here! $5,000 Sign-on bonus $1,800-$2,600 Weekly earnings potential, depending on the home time you're looking for $.80 CPM loaded, $0.60 CPM empty Details Flexible home time Various home time options. If you want to stay out 1 night per week or up to 10 day...
CDL-A Truck Drivers: GREAT ROUTES AVAILABLE! Top Pay & Benefits OTR Drivers: Average 2,000+ miles per week. Bonuses may be available. Count on consistent miles and paycheck with flexible home time that works for you.Regional Opportunities: Drive regional and earn strong pay and dependable miles with the confidence of knowing you'll be home e...
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.