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.
Drive your career forward with our dedicated job board for driving-based roles across the UK. Whether you're an experienced driver or looking to enter the profession, our platform offers a wide range of opportunities in logistics, delivery, public transport, and more. Stay ahead of the competition with our up-to-date listings from reputable employers seeking skilled drivers. Explore diverse positions that match your qualifications and preferences. Begin your search today and accelerate your career in the driving sector with our comprehensive job offerings.
18 jobs for The Gainey Agency in Chicago
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...
REGIONAL OTR JOBS OPEN NOW FOR CDL-A TRUCK DRIVERS! Family-owned McLeod Express is now hiring forCDL-A regional and OTR truck driver jobs with excellent earning potential! Advantages and earnings include: Multiple routes available! Regional Routes: Earn $65,000-$75,000/year Pay Protection of $1,000/week Home Weekends! OTR Routes: Earn $0....
CDL-A Truck Drivers: GREAT ROUTES AVAILABLE! Top Pay & Benefits OTR Drivers: Average 2,000+ miles per week. Bonuses may be available. Count on consistent miles and paycheck with flexible home time that works for you.Regional Opportunities: Drive regional and earn strong pay and dependable miles with the confidence of knowing you'll be home e...
KAG Specialty Products is hiring OTR CDL A Drivers who want to stay out, run hard, and earn BIG.If you're willing to stay "in system" for at least 14 consecutive days, this is one of the highest earning mileage packages in the industry.CDL A OTR Drivers - High Mileage = High Money $110,000+ W 2 Text APPLY to to get your quick app started! Pay Pa...
KAG Specialty Products is hiring OTR CDL A Drivers who want to stay out, run hard, and earn BIG.If you're willing to stay "in system" for at least 14 consecutive days, this is one of the highest earning mileage packages in the industry.CDL A OTR Drivers - High Mileage = High Money $110,000+ W 2 Text APPLY to to get your quick app started! Pay Pa...
OTR & Regional CDL-A Tanker Drivers! CORE48 Transport, LLC is a bold, new name in trucking - we're rebranding what it means to drive with a company that truly cares. As a third-generation transportation leader, we honor nearly 60 years of excellence with a fresh, driver-first approach to Tanker, Reefer, and Dry Van freight. We offer top-notch bene...
CDL-A Dedicated Reefer Truck Driving Job - (Earn $1,400-$1,600/Wk)
NewPosted 21 May 2026Little River TransportationCDL-A Reefer OTR Truck Driver - Dedicated Power Lanes Earn $75,000+ Annually & Get Home Every Other Weekend! Little River Transportation is hiring CDL-A Company Reefer OTR Truck Drivers to run dedicated reefer power lanes with consistent, predictable freight. If you're looking for a small company with great communication and a strong network of st...
OTR CDL-A Reefer Truck Driver Job - ($1,400-$1,600/Wk Avg)
NewPosted 21 May 2026Little River TransportationCDL-A Reefer OTR Truck Driver - Dedicated Power Lanes Earn $75,000+ Annually & Get Home Every Other Weekend! Little River Transportation is hiring CDL-A Company Reefer OTR Truck Drivers to run dedicated reefer power lanes with consistent, predictable freight. If you're looking for a small company with great communication and a strong network of st...
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.