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.

679 jobs for Highway Driver Leasing in Chicago

$240,000 per annum

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...

$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...

$86,000 per annum

Looking for regional truck driving jobs? J.B. Hunt is hiring intermodal truck drivers! Drive with J.B. Hunt Intermodal and enjoy express access railyard gates, onsite maintenance and 100% company-owned equipment. This position is an activity-based pay plan that encourages safety, efficiency and a strong work ethic.Drivers are averaging $86,000 a ye...

$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...

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 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 ...

$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...

$300,000 per annum

Hiring CDL-A Owner Operators GROSS BIG. KEEP MORE. - Top 25% earn $300K+ annually* RUN HARD. RESET HOME. - Most contractors are home weekends CONTRACTOR SUPPORT THAT PAYS OFF - Fuel, maintenance, and roadside savings Why Partner with Page Trucking? At Page Trucking, Owner Operators get the freedom of running their own business w...

$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...

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.

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