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.
156 jobs for Highway Driver Leasing in Chicago
CDL-A Linehaul Truck Driver, Full-time. Job Description Road Drivers are responsible for the pickup and delivery of cargo trailers to and from various long-distance destinations. Responsibilities Performing various tasks ranging from check-in, tractor/trailer inspection, tractor set up and the pickup and delivery of cargo. Actual duties and sched...
Overview: Imagine a career that truly takes you places, where you get to travel and meet new people every day along the journey. For 100 years, our Greyhound Drivers have been the heart and soul of our company, serving the transportation needs of communities across the nation. Do you enjoy meeting new people and have a passion for safety and the c...
Truck Driver Company - 2yrs EXP Required - OTR - Dry Van - $1.5k - $1.85k per week - Seward Motor Freight, Inc.
NewPosted 23 May 2026Seward Motor FreightHiring CDL-A Drivers | OTR Positions Available . Seward Motor Freight Inc. Is Hiring Reliable/Experienced CDL A Truck Drivers. OTR Routes Available We Offer: Earn between $1,500 - $1,850 per week based on experience and miles No slip seating. Truck is yours until you're promoted out of it. We run 30-35 drivers per Driver Manager. They will kno...
CDL-A Company Driver - 2yrs EXP Required - OTR - Dry Van - $1.5k - $1.85k per week - Seward Motor Freight, Inc.
NewPosted 23 May 2026Seward Motor FreightHiring CDL-A Drivers | OTR Positions Available . Seward Motor Freight Inc. Is Hiring Reliable/Experienced CDL A Truck Drivers. OTR Routes Available We Offer: Earn between $1,500 - $1,850 per week based on experience and miles No slip seating. Truck is yours until you're promoted out of it. We run 30-35 drivers per Driver Manager. They will kno...
Class A CDL Company Driver - 2yrs EXP Required - OTR - Dry Van - $1.5k - $1.85k per week - Seward Motor Freight, Inc.
NewPosted 23 May 2026Seward Motor FreightHiring CDL-A Drivers | OTR Positions Available . Seward Motor Freight Inc. Is Hiring Reliable/Experienced CDL A Truck Drivers. OTR Routes Available We Offer: Earn between $1,500 - $1,850 per week based on experience and miles No slip seating. Truck is yours until you're promoted out of it. We run 30-35 drivers per Driver Manager. They will kno...
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.