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.
674 jobs for Southwest Truck Driving Training in Chicago
OTR CDL-A Reefer Truck Driver Job - ($1,400-$1,600/Wk Avg)
NewPosted 21 May 2026Little River TransportationCDL-A Reefer OTR Truck Driver - Dedicated Power Lanes Earn $75,000+ Annually & Get Home Every Other Weekend! Little River Transportation is hiring CDL-A Company Reefer OTR Truck Drivers to run dedicated reefer power lanes with consistent, predictable freight. If you're looking for a small company with great communication and a strong network of st...
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...
Entry-Level & Experienced Drivers Welcome May Trucking Company is hiring Over-the-Road CDL-A Company Truck Drivers.Whether you are new to the industry or have years of experience, we offercompetitive pay, modern equipment, and driver-focused benefits designed tosupport you and your family. Pay & Compensation $0.45 – $0.60 CPM based on experience...
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...
Entry-Level & Experienced Drivers Welcome May Trucking Company is hiring Over-the-Road CDL-A Company Truck Drivers.Whether you are new to the industry or have years of experience, we offercompetitive pay, modern equipment, and driver-focused benefits designed tosupport you and your family. Pay & Compensation $0.45 – $0.60 CPM based on experience...
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...
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...
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...
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.