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.
156 jobs for Highway Driver Leasing in Chicago
Flatbed OTR Class A CDL Driver - $1,094.00 - $2,103.53 per week. Full Benefits
NewPosted 21 May 2026System TransportJob Description:CDL A OTR Flatbed Driver: $1,094.00 - $2,103.53 per week. Full BenefitsAMERICA 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 transporti...
Class A CDL Flatbed OTR Driver: Earn $1,094.00 - $2,103.53 per week. Full Benefits
NewPosted 23 May 2026System TransportCDL A OTR Flatbed Driver: $1,094.00 - $2,103.53 per week. Full BenefitsAMERICA 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 goo...
CDL A Driver: Earn $101,176 yr with 1 yr or more driving experience!
NewPosted 16 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 often? We ve...
12 Days Out CDL A Driver Job -Top 50% average $92,163 / $.61 to $.64 cpm
Posted 11 May 2026Crete Carrier Corporation> 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 pay on AL...
12 Days Out CDL A Driver Job -Top 50% average $92,163 / $.61 to $.64 cpm
NewPosted 21 May 2026Crete Carrier Corporation> 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 pay on AL...
$5K Hiring Bonus Flatbed Class A CDL Regional Driver: Earn $1,095.18 - $1,980.65 per week. Off Most Weekends
NewPosted 23 May 2026System Transport$5K Hiring Bonus! Flatbed CDL-A Driver, Regional Route: $1,095.18 - $1,980.65 per week. Most Weekends off!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 ...
Illinois has OTR CDL A flatbed driver jobs-1 yr. experience required
NewPosted 21 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-earning dr...
Illinois has OTR CDL A flatbed driver jobs-1 yr. experience required
Posted 11 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-earning dr...
Driver Contractors With or Without Own Tow Vehicle Local Regional OTR and Next Day Pay
Posted 14 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 a...
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...
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.