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.
172 jobs for Cwt Driver Advocates in Chicago
CDL-A HAZMAT Tanker Driver - $.80 CPM loaded, $0.60 CPM empty
NewPosted 25 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...
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...
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...
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...
> 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...
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...
Truck Driver Company - 2yrs EXP Required - OTR - Dry Van - $1.75k per week - Turquoise Trucking
NewPosted 23 May 2026Turquoise TruckingOTR Company Drivers | $10,400 Sign-On | Avg $1,750 Weekly. Drive For Us We are always looking for OTR company drivers and owner operators to join our family. Here, we know you by name, not by number. Drive Turquoise. Company Drivers Guaranteed* min. $1400 per week/driver, average $1750 per week $10,400 sign-on bonus On average, our company driv...
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.