Highway Driver Leasing Jobs in Chicago

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.

96 jobs for Highway Driver Leasing in Chicago

$110,000 per annum

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...

$110,000 per annum

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...

$110,000 per annum

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...

$81,000 per annum

Millis Transfer is now hiring Regional CDL-A Drivers in the Midwest! Top 25% of Drivers Earn $81,000+ Annually Guaranteed Home Weekly - New Pay Increase! Applicants must have 6 Months of OTR experience. Applicants must have a Valid Class A CDL. Millis Drivers Enjoy: Drivers average $1,600 per week Top 25% of Midwest Regional drivers earn $81...

$110,000 per annum

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...

$1,400 - $1,700 per week

Terminals located in both Lansing, IL and Channahon, IL Rewarding Career Starts Here! $5,000 Sign-onbonus $1,400-$1,700 Weekly earnings Loads under 200 miles paid at $30/hour Loads over 200 miles paid $0.65 CPM $50 Accessorial pay for loading/unloading Details Home daily Hauling liquid chemicals in a liquid tanker Company Benefits ...

$65,000 - $75,000 per annum

REGIONAL OTR JOBS OPEN NOW FOR CDL-A TRUCK DRIVERS! Family-owned McLeod Express is now hiring forCDL-A regional and OTR truck driver jobs with excellent earning potential! Advantages and earnings include: Multiple routes available! Regional Routes: Earn $65,000-$75,000/year Pay Protection of $1,000/week Home Weekends! OTR Routes: Earn $0....

CLASS A DRIVERS  READY TO OWN YOUR TRUCK AND YOUR FUTURE? Lease Purchase Built for Drivers Who Want More. This is not for everyone. Must have 12 months of verifiable OTR Experience. This is for drivers who are done settling and ready to level up. Own your truck Build real, long-term financial freedom Run consistent refrigerated freigh...

CLASS A DRIVERS READY TO OWN YOUR TRUCK AND YOUR FUTURE?Lease Purchase Built for Drivers Who Want More.  Own your truck Build real, long-term financial freedom Run consistent refrigerated freight Partner with a carrier that respects your grind Take full control of your future Because here, you are not just another truck number, you are part of ...

$100,000 per annum

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. Drivers in this position over the last six...

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.

An unhandled error has occurred. Reload 🗙