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.
184 jobs for Cwt Driver Advocates in Chicago
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...
CDL-A OTR Reefer Driver - Up to $90K Per Year + $3,000 Sign-On Bonus
NewPosted 26 May 2026California Overland, Ltd.We're seeking experienced CDL-A drivers to join our team hauling refrigerated freight across the country. Drive the newest trucks on the road without the headache of maintenance or upkeep. All tractors and trailers are company-owned and fully maintained by California Overland. This is an over-the-road position with competitive pay, comprehensive ...
CDL-A Lease Driver - 6mo EXP Required - Local - Intermodal - $4k - $5k per week - Universal Logistics
NewPosted 26 May 2026universal logisticsSeeking Owner Operators in Harvey, IL | Local & Regional Freight. Pay: $4,000.00 - $5,000.00 per week Join a dynamic fleet that works for you! Universal Intermodal's Harvey location offers a contractor focused facility that offers the freight options you need. Universal boasts a mixture of freight to fit your schedule. Day shift & Overnight runs...
Driver Contractors With or Without Own Tow Vehicle Local Regional OTR and Next Day Pay
NewPosted 25 May 2026TruckMoversJob Description: Driver Contractors With or W/O Own Tow Vehicle Great Pay - Next Day! Local, Regional & OTR Class A or B! Be your own boss! Company Profile: TruckMovers drivers are independent contractors and have the freedom to operate on their own schedule. You choose the types of loads you deliver. Your investment in equipment is minimal ...
Truck Driver Company - 6mo EXP Required - OTR - Dry Van - $1.2k - $1.5k per week - Bison Transport Inc.
NewPosted 24 May 2026BISON TRANSPORTBison Transport is Hiring CDL-A Drivers in Your Area!. OTR Drivers: OTR drivers earn $1,320 - $1,408 per week ($68,640 - $73,216 annually) $5,000 sign on bonus for all OTR drivers with 6+ months experience! OTR Runs — Stay out 2-3 weeks, run solid miles. Regional Drivers: Regional drivers earn $1,197 - $1,503 per week ($62,244 - $78,162 annually...
CDL A Lease Purchase Opportunities With ATS | Flatbed OTR. The Lifestyle You Want. The Support You Need To Get There. You chose a truck driving career because it gave you freedom. Now you want more control over your lifestyle, so you're thinking about leasing options . Get the support you need to be successful with one of the best lease-purchase...
Class A CDL Lease Driver - 6mo EXP Required - Local - Intermodal - $4k - $5k per week - Universal Logistics
NewPosted 26 May 2026universal logisticsSeeking Owner Operators in Harvey, IL | Local & Regional Freight. Pay: $4,000.00 - $5,000.00 per week Join a dynamic fleet that works for you! Universal Intermodal's Harvey location offers a contractor focused facility that offers the freight options you need. Universal boasts a mixture of freight to fit your schedule. Day shift & Overnight runs...
CDL-A Company Driver - 6mo EXP Required - OTR - Dry Van - $1.2k - $1.5k per week - Bison Transport Inc.
NewPosted 24 May 2026BISON TRANSPORTBison Transport is Hiring CDL-A Drivers in Your Area!. OTR Drivers: OTR drivers earn $1,320 - $1,408 per week ($68,640 - $73,216 annually) $5,000 sign on bonus for all OTR drivers with 6+ months experience! OTR Runs — Stay out 2-3 weeks, run solid miles. Regional Drivers: Regional drivers earn $1,197 - $1,503 per week ($62,244 - $78,162 annually...
CDL A Lease Purchase Opportunities With ATS | Flatbed OTR. The Lifestyle You Want. The Support You Need To Get There. You chose a truck driving career because it gave you freedom. Now you want more control over your lifestyle, so you're thinking about leasing options . Get the support you need to be successful with one of the best lease-purchase...
Class A CDL Company Driver - 6mo EXP Required - OTR - Dry Van - $1.2k - $1.5k per week - Bison Transport Inc.
NewPosted 24 May 2026BISON TRANSPORTBison Transport is Hiring CDL-A Drivers in Your Area!. OTR Drivers: OTR drivers earn $1,320 - $1,408 per week ($68,640 - $73,216 annually) $5,000 sign on bonus for all OTR drivers with 6+ months experience! OTR Runs — Stay out 2-3 weeks, run solid miles. Regional Drivers: Regional drivers earn $1,197 - $1,503 per week ($62,244 - $78,162 annually...
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.