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.
54 jobs for Highway Driver Leasing in Chicago
Job Description: CDL CLASS A DRIVERS UP TO $0.70 CPM NEWER TRUCKS TONS OF MILESWe're growing and looking for pros who want great miles, smooth dispatch, and real support.Why drive with us Up to $0.70 per mile (experience & performance) Newer equipment tractors not older than 3 years Plenty of miles stay rolling and earning 24/7 support + ...
OTR CDL A Driver Home Every Weekend, Dedicated Lanes
NewPosted 22 May 2026Green Lines Transportation, Inc.Job Description: OTR CDL A Driver Home Every Weekend, Dedicated LanesCall ex. 218 Immediately! These opportunities won t last long! Green Lines Transportation is looking for CDL A Flatbed Drivers. We are busy. We have been Family Owned and Operated for over 30 years. We are one of the top paying carriers in the Industry while maintaining excellen...
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...
Class A CDL Flatbed OTR Driver: Earn $1,094.00 - $2,103.53 per week. Full Benefits
NewPosted 23 May 2026System TransportCDL 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 transporting important goo...
CDL-A OTR Flatbed Driver: Earn $1,094.00 - $2,103.53 per week. Full Benefits
NewPosted 23 May 2026System TransportCDL 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 transporting important goo...
$5K Hiring Bonus Flatbed Class A CDL Regional Driver: Earn $1,095.18 - $1,980.65 per week. Off Most Weekends
NewPosted 23 May 2026System Transport$5K Hiring Bonus! Flatbed CDL-A Driver, Regional Route: $1,095.18 - $1,980.65 per week. Most Weekends off!AMERICA 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 ...
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...
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...
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 ...
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...
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.