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.
664 jobs for Southwest Truck Driving Training in Chicago
Job Description: CDL-A Truck Driver Midwest Regional Home SAT & Sun for 34 Reset $4,000 Sign On Bonus Run Midwest-Chi Based Up to .64 CPM Consistent Home time Top 20% earn $1,550+ Weekly Excellent Benefits Package Health, Dental, Vision Consistent Miles and Paychecks 100% No Touch Freight 2021 or Newer Freightliner Cascadia or KW Rider and Pet ...
Flatbed OTR Class A CDL Driver - $1,094.00 - $2,103.53 per week. Full Benefits
Posted 11 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...
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 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...
Call Smith Today at Job Description: CDL-A OTR TRUCK DRIVER JOBS Must have at least 1 year recent CDL-A OTR Experience Home Weekly on Week Days 48 Hours - Off Either Tuesday & Wednesday or Wednesday & Thursday Come see what it means to have it all at Smith Transport - the best company driver equipment, steady dedicated freight, predictable ...
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
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...
CDL-A OTR Company Driver - Affordable Benefits Package + $98,280 Per Year Per Driver
Posted 11 May 2026ForwardJob Description:Searching for a company that values team drivers and rewards your miles? Forward is actively hiring team Class A OTR Company Drivers in your area! When driving with Forward, you can expect consistent miles, industry-leading benefits and a competitive per-mile rate - paid to you based on your team's total miles. What makes this oppo...
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...
Job Description: CDL A Lease Purchase Driver Apply today or call us at Pay: $2,000.00 - $3,000.00 per week Job description: Join our team based out of our main yard in Chicago, Illinois, and take advantage of this incredible lease-to-own opportunity! With our transparent pay structure and premium trucks, you can focus on your driving career ...
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.