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
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...
Richards Building Supply Co. is currently searching for a CDL Class A or B Driver for our Belmont Ave, Chicago, IL Location.Opportunity to learn industry equipment such as the Moffett and the Knuckleboom Our delivery drivers are responsible for safely delivering products to the job site and physically unloading material per the customer's request...
Hiring CDL-A Truck Drivers PREMIUM PAY, EVERY DAY - Experienced drivers start at 70 CPM BIG BONUS, BETTER BENEFITS - $1,000 sign-on + PTO + full benefits WEEKLY HOME TIME TO STAY FRESH - Get home every weekend! Why Drive for K&B Transportation? K&B Transportation is growing in your area. We are hiring experienced Class A CDL Truck Drive...
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...
Flatbed CDL Driver, All Routes: $903.01 - $2,119.33/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 all routes! We offer regional, local, dedicated, and OTR routes. As a ...
Flatbed CDL-A 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...
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...
Looking for dedicated truck driving jobs? J.B. Hunt is hiring local CDL-A drivers! Become a Dedicated Contract Services® driver and start enjoying consistent freight and deliveries for a single customer. This position is an activity-based pay plan that encourages safety, efficiency and a strong work ethic. Job Details: $0.23-$0.25 per mile Stop pa...
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.