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.
215 jobs for Cwt Driver Advocates in Chicago
CDL-A Company Driver - Grad Training - Regional - $60k - $70k per year - KreilKamp Trucking
NewPosted 26 May 2026Kreilkamp TruckingRegional CDL A Drivers | NEW Grads Welcome | Earn $70,000+ Annually. We're proud to be a 4th generation family truck line, started in 1935, but even prouder that over 350 drivers call us home. As we continue to grow, there's plenty of room at the table for professional drivers like you. No experience? No problem! We are currently accepting recent...
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...
Truck Driver Company - 1yr EXP Required - OTR - Flatbed - $85k - $95k per year - Koch Trucking
NewPosted 26 May 2026Koch TruckingHiring CDL-A Truck Driver – Flatbed Division. Job Highlights: Average annual earnings: $85K Starting pay: $0.61 - $0.63CPM based on experience Top performer earnings: $95K Home time: Out 14-21 days based on location Hiring bonus: $6,000 Stop pay: $30/stop Securement pay; $25/stop Tarp pay: $50/stop Over dimensional pay: $75-$200 based...
Class A CDL Company Driver - 1yr EXP Required - OTR - Specialized - $85k - $100k per year - Koch Trucking
NewPosted 24 May 2026Koch TruckingCDL-A Truck Driver – Specialized Division | Earn $85K - $100K+. Job Highlights: Average annual earnings: $85K Starting pay: $0.58 - $0.60CPM Top performer earnings: +$100K Home time: Out 14-21 days Hiring bonus: $6,000 Setup pay: $75 per load Stop pay: $30 per stop after first stop Average Weekly Miles: +2400 All trucks are 3 years ol...
Truck Driver Company - 1yr EXP Required - OTR - Specialized - $85k - $100k per year - Koch Trucking
NewPosted 24 May 2026Koch TruckingCDL-A Truck Driver – Specialized Division | Earn $85K - $100K+. Job Highlights: Average annual earnings: $85K Starting pay: $0.58 - $0.60CPM Top performer earnings: +$100K Home time: Out 14-21 days Hiring bonus: $6,000 Setup pay: $75 per load Stop pay: $30 per stop after first stop Average Weekly Miles: +2400 All trucks are 3 years ol...
> 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 often? We ve raised p...
Illinois has OTR CDL A flatbed driver jobs-1 yr. experience required
NewPosted 25 May 2026Hunt TransportationTRUCK DRIVING JOBS: WE ARE HIRING DRIVERS! We're a Certified Top Pay Carrier and the top 50 percent of our drivers average $93,347 per year. NOW HIRING: Job Description: Drivers who want to see the country are a perfect fit for the Hunt Transportation national OTR fleets. These are our highest mileage fleets and home to our top...
Class A CDL Company Driver - Grad Training - Regional - $60k - $70k per year - KreilKamp Trucking
NewPosted 24 May 2026Kreilkamp TruckingRegional CDL A Drivers | NEW Grads Welcome | Earn $70,000+ Annually. We're proud to be a 4th generation family truck line, started in 1935, but even prouder that over 350 drivers call us home. As we continue to grow, there's plenty of room at the table for professional drivers like you. No experience? No problem! We are currently accepting recent...
Class A CDL Company Driver - 2yrs EXP Required - Regional - Dry Van - Road Warrior Staffing
NewPosted 26 May 2026Road Warrior StaffingHelping CDL A Drivers Find Their Perfect Match!. Road Warrior Staffing is your partner in CDL driving careers. We specialize in placing qualified drivers with top companies nationwide, offering steady opportunities, competitive pay, and a team that understands the industry. Drivers can earn an average of $1,400–$2,500 per week, with additional CP...
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.