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Posted June 15, 2026
Classic Transportation Services Inc.

CDL A Local Intermodal Owner Operator in Chicago, IL

Classic Transportation Services Inc.
1127 South Chicago Street, Joliet, Illinois, United States Full Time

Owner Operators — Be Home Every Day & Earn Strong Daily Pay Spend More Time at Home Without Sacrificing Your Income

Are you tired of long hauls and missing time with your family? At Classic Transportation & Warehousing, you can enjoy consistent work, excellent pay, and the ability to be home every day.

We’re currently hiring experienced Class A CDL Owner Operators to run dedicated daily routes.

Compensation

  • Average Gross Daily Pay: $810
    • $800 Monthly Dispatch Bonus
    • $1,050 Quarterly Safety Bonuses
    • Sign-On Bonus of $1,500
    • Referral Bonus of $1,500 after 120 days worked
  • Settlements paid via direct deposit weekly

Highlights

  • Will operate under Classic Transportation Services authority
  • 24/7 Dispatch and Support
  • Family-oriented company culture
  • Friendly, driver-focused dispatchers
  • Consistent routes and dependable freight
  • Seasonal Opportunities Available
  • Fuel Taxes Paid
  • AD&D insurance
  • Disability insurance
  • Fuel card
  • Fuel discount
  • Paid orientation
  • Paid toll fees
  • Paid training
  • Safety equipment provided

Home Time, Route, & Schedule

  • Home Daily!
  • Route:
    • Chicago to West Michigan
  • Day shift with no forced dispatch
  • Level of Touch: No touch

Equipment Requirements

  • Must have your own truck (2014 and above); Must be ELD compatible.

Qualifications

  • Must be at least 21 years of age
  • Valid Commercial Driver's License (CDL) Class A with a clean driving record.
  • Minimum of 1-year of professional driving experience with a verifiable safety record
  • Hazmat Endorsement preferred
  • No more than 10 jobs in 3 years
  • No more than 3 moving violations in past 3 years
  • No more than 3 accidents in the past 5 years
  • No truck abandonment
  • Familiarity with state and federal regulations governing the transportation industry.
  • Strong attention to detail and commitment to safety and compliance.
  • Excellent communication and customer service skills.
  • Basic computer skills for electronic logs and communication.
  • Ability to pass a DOT physical and possess a valid DOT medical card
  • Partnering with drivers within 50 miles of Chicago, IL