---
title: Owner Operator Independent Contractor
description: Legacy Transportation Services is hiring for the Owner Operator Independent Contractor
  role in Chicago, IL. See the full description and apply.
type: job
url: https://www.foundrole.com/jobs/owner-operator-independent-contractor-at-legacy-transportation-services-inc-01a0b3c6-2b6f-76af-a393-35f99609f029
date: 2026-09-28T21:37:49Z
og_description: Join Legacy Transportation Services as Owner Operator Independent Contractor in
  Chicago, IL. Pays $200K–$300K per year.
og_image: https://www.foundrole.com/og/0pivzn.png
breadcrumbs:
  - label: Home
    url: https://www.foundrole.com/
  - label: Search
    url: https://www.foundrole.com/jobs
---

| | |
|---|---|
| **Company** | Legacy Transportation Services |
| **Location** | Chicago, IL |
| **Salary** | $200K/yr - $300K/yr |
| **Type** | Contractor |
| **Posted** | Sep 28, 2026 |
## Description

**DRIVE ELITE. EARN $200K–$300K+.**

****Sign-On Bonus $5000.00 FIRST 6 MONTHS.**

**Legacy Transportation Services is seeking experienced Owner-Operator Independent Contractor Drivers** to haul high-value, sensitive freight throughout all 48 states.

We partner with professional drivers who value precision, reliability, strong communication, and representing a premium carrier. If you are ready for specialized freight, consistent opportunity, and a company that respects your experience, this may be the right fit for you.

*What You Can Earn*

**• $200,000–$300,000+** annual earning potential based on acceptance and completion of dispatched loads.

**• Earn up to a $5,000** earned onboarding bonus during your first 6 months

**•** Compensation based on gross revenue and accepted loads

**•** Use company trailer

**• Weekly pay**

**• Flexible home time**

**•** Specialized, high-value freight

**•** Partner with a respected, professional transportation company

Learn more about Legacy at [**www.legacytsi.com**](http://www.legacytsi.com/)

**Qualifications:**

- Valid **Class A CDL**
- Current **DOT Medical Card**
- Minimum **21 years of age**
- Own a **CARB-compliant tractor** eligible for California operations
- **Must be an owner-operator** eligible to work as an independent contractor
- Ability to run in all 48 states and Canada (if applicable)
- Strong communication skills and punctuality
- Willingness to **live load/unload freight** and **secure freight inside trailer**
- Professional attitude and commitment to excellence

*Ready to Drive With the Best?*

**Call our Recruiting Team today: (408) 213-6345**

Get your questions answered and take the next step toward building your future with Legacy.

**Take the wheel. Drive your success. Build your legacy with** ***LEGACY*** **Transportation Services.**

**As Milestones are met.
## Skills

- Material Handling
- Owner-Operator
- Punctuality
- Commercial Driver's License
- Communication
- DOT Medical Certification

## How to Apply

[Apply for this position](https://www.foundrole.com/jobs/owner-operator-independent-contractor-at-legacy-transportation-services-inc-01a0b3c6-2b6f-76af-a393-35f99609f029?utm_source=ai_markdown)

## Related

- [Browse all companies](https://www.foundrole.com/companies?utm_source=ai_markdown)