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.
169 jobs for Cwt Driver Advocates in Chicago
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 OTR Class A CDL Driver - $1,094.00 - $2,103.53 per week. Full Benefits
NewPosted 25 May 2026System TransportJob Description: CDL 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 transpo...
CDL A Driver: Earn $101,176 yr with 1 yr or more driving experience!
NewPosted 25 May 2026Crete CarrierJob Description: TRUCK DRIVING JOBS: WE ARE HIRING DRIVERS! INCREASED DRIVER STARTING PAY AT CRETE CARRIER, INDUSTRY LEADING PAY IS JUST THE BEGINNING Yes, you read that right: with a $0.03 per mile raise for our OTR fleet, with the top 50% of our OTR drivers averaging over $101,000 annually. Need to get through the house more of...
CDL-A Company Driver - 6mo EXP Required - OTR - Dry Van - $1.5k per week - Pam Transport Inc.
NewPosted 24 May 2026PAM TransportHiring CDL-A Truck Drivers Near You!. CDL-A Truck Driver Don't miss out! Join PAM now as an experienced truck driver! Call us today to speak with a recruiter! About PAM: Join a company that's been driving success for over 40 years. PAM Transport started in 1980 with just five trucks and has grown into an international carrier serving the U.S.,...
Class A CDL Company Driver - 6mo EXP Required - OTR - Dry Van - $1.5k per week - Pam Transport Inc.
NewPosted 24 May 2026PAM TransportHiring CDL-A Truck Drivers Near You!. CDL-A Truck Driver Don't miss out! Join PAM now as an experienced truck driver! Call us today to speak with a recruiter! About PAM: Join a company that's been driving success for over 40 years. PAM Transport started in 1980 with just five trucks and has grown into an international carrier serving the U.S.,...
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...
OTR CDL-A Flatbed Driver: Earn $1,094.00 – $2,103.53 per week. Full Benefits
NewPosted 25 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 Class A CDL OTR Driver: Earn $1,094.00 – $2,103.53 per week. Full Benefits
Posted 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...
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.