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.
44 jobs for Southwest Truck Driving Training 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...
Hiring CDL-A Truck Drivers PAY THAT DELIVERS - Earn up to $120,000 per year SPECIALIZED FREIGHT, STRONG START - Drivers get a $2,500 sign on bonus PERKS THAT STACK - 100% paid medical premium, paid holidays, bonuses & more Why Drive for E.W. Wylie? Choosing the right carrier is about more than miles and money-it's about respect, support, and lo...
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...
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...
KAG Specialty Products is hiring CDL-A Owner Operator Truck Drivers to haul specialty products nationwide. If you're looking for high earning potential, consistent freight, and OTR runs, this is the opportunity for you.OTR Owner Operators – Big Miles. Big Money. Real Support. | $240,000/year Text APPLY to to get your quick app started! Why Ow...
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...
KAG Specialty Products is hiring CDL-A Owner Operator Truck Drivers to haul specialty products nationwide. If you're looking for high earning potential, consistent freight, and OTR runs, this is the opportunity for you.OTR Owner Operators – Big Miles. Big Money. Real Support. | $240,000/year Text APPLY to to get your quick app started! Why Ow...
Looking for dedicated truck driving jobs? J.B. Hunt is hiring regional CDL-A drivers! Become a Dedicated Contract Services® driver and start enjoying consistent freight and deliveries for a single customer. This position is an activity-based pay plan that encourages safety, efficiency and a strong work ethic. Job Details: $0.55-$0.57 per mile St...
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.