DriverRoll

OTR CDL-A Flatbed Team Driver — $2,000/Week Flat Pay

Chicago, IL Posted Sep 3, 2026

  • Heavy Haul
  • OTR

Pay

$2,000 - $3,000/wk

Location
Chicago, IL
Equipment
Heavy Haul
Route
OTR · USA only
License
CDL A
Position
Company driver
Experience
2+ years

About this job

This is a team OTR flatbed role hauling freight between the Midwest and Southeast, running a 2022 Kenworth T680 automatic. You'll handle long-haul lanes while keeping safety and documentation sharp along the way.

Pay

  • Flat $2,000 weekly base, with total pay ranging $2,000.00 - $3,000.00 per week depending on bonuses
  • Extra bonuses available for additional days worked, tarping, and other situational conditions

What you'll haul

  • Flatbed trailer freight, loaded to 100% of the rated weight limit, with proper securement (training provided)
  • You'll take photos of the load before and after securing it and again before unloading, to protect against broker or customer claims

Routes

  • Over-the-road lanes connecting the Midwest and Southeast regions
  • You'll plan stops and routes using fleet GPS tools such as Macropoint or Truckers Tools, and fuel up at truck stops like Loves and TA/Petro

What the job involves

  • Pre-trip and post-trip vehicle checks, watching for issues like air brake problems, tire wear, and oil or coolant leaks
  • Staying in touch with dispatch about delivery status, delays, breakdowns, or inspection holds
  • Keeping accurate logs, shipment paperwork, and safety records
  • Treating customers professionally and handling their questions courteously during deliveries

Requirements

  • Valid CDL-A with at least 2 years of driving experience
  • No more than 3 traffic violations on your record
  • Must pass drug screening; zero tolerance policy, with no prior positive results or refusals
  • Flatbed hauling experience required; background with heavy equipment or heavy haul is a plus
  • Comfortable driving in rough weather while keeping safety standards up
  • Basic mechanical know-how to spot common truck problems during inspections

Benefits

  • On-the-job training provided
  • Safety equipment supplied

This is a team position based on the road, running routes out of the Chicago, IL area for our company Inc.

The hiring carrier's name is shared with you once you apply through the DriverRoll app, where you can message them directly.

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