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.
669 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...
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 ...
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 Stop p...
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 Stop p...
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:...
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:...
Contracting CDL-A Truck Drivers EARN TODAY. OWN TOMORROW - Up to $1,650 weekly take-home PAID TO GET STARTED - $5,000 sign-on bonus + $500 orientation pay EASY FREIGHT. EASY WEEKS. - 100% no-touch dry van, 60% drop & hook Why Drive for Riverside Transport? At Riverside Transport, drivers aren't just numbers on a board - they're part of the family...
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...
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.