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.
638 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...
Looking for dedicated truck driving jobs? J.B. Hunt is hiring local 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: $0.23-$0.25 per mile Stop pay:...
Hiring CDL-A Truck Drivers PAY THAT GOES THE DISTANCE - Drivers can earn $0.62 - $0.66CPM GREAT TRUCKS, EASY MILES - Late-model equipment, 100% no-touch freight OWN MORE THAN YOUR ROUTE - ESOP ownership means your miles build equity Why Drive for J&R Schugel? At J&R Schugel, drivers aren't just hauling freight - they're building a future. Our OT...
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...
Top drivers earn up to $75,000 Average pay: $1,130-$1,390 weeklyHome time: DailyExperience: 6 months or greater CDL experienceJob ID: 240289 Overview Haul freight containers secured to company-owned chassis. 100% no-touch freight that is 50% drop-and-hook. Drive a tractor from Schneider's pool of 150+ day cabs. No assigned trucks. Drive in and ou...
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...
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
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...
Job Title: Driver Training Manager Job Location: Des Plaines-USA-60016 Work Location Type: On-Site Salary Range: $75,615.05 - 94,518.82 About us LSG Sky Chefs is one of the world’s largest airline catering and hospitality providers, known for its outstanding reputation and dynamic approach in the industry. Voted “Airline Caterer o...
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...
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.