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Local Owner Operator Trucking Jobs in Wisconsin (NOW HIRING)

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Owner Operator driver

Milwaukee, WI · On-site

$3.5K - $5.0K/wk

We provide freight opportunities for Sprinter Vans and Straight Trucks, with local, regional, and ... Owner-operators work with our 24/7 dispatch and tracking team while maintaining the freedom to ...

New

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Owner Operator driver

Milwaukee, WI · On-site

$3.5K - $5.0K/wk

We provide freight opportunities for Sprinter Vans and Straight Trucks, with local, regional, and ... Owner-operators work with our 24/7 dispatch and tracking team while maintaining the freedom to ...

New

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Owner Operator driver

Milwaukee, WI · On-site

$3.5K - $5.0K/wk

We provide freight opportunities for Sprinter Vans and Straight Trucks, with local, regional, and ... Owner-operators work with our 24/7 dispatch and tracking team while maintaining the freedom to ...

New

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Owner Operator driver

Milwaukee, WI · On-site

$3.5K - $5.0K/wk

We provide freight opportunities for Sprinter Vans and Straight Trucks, with local, regional, and ... Owner-operators work with our 24/7 dispatch and tracking team while maintaining the freedom to ...

New

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Van Owner Operator

Milwaukee, WI · On-site

$3.5K - $5.0K/wk

We provide freight opportunities for Sprinter Vans and Straight Trucks, with local, regional, and ... Owner-operators work with our 24/7 dispatch and tracking team while maintaining the freedom to ...

New

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Van Owner Operator

Milwaukee, WI · On-site

$3.5K - $5.0K/wk

We provide freight opportunities for Sprinter Vans and Straight Trucks, with local, regional, and ... Owner-operators work with our 24/7 dispatch and tracking team while maintaining the freedom to ...

New

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Van Owner Operator

Milwaukee, WI · On-site

$3.5K - $5.0K/wk

We provide freight opportunities for Sprinter Vans and Straight Trucks, with local, regional, and ... Owner-operators work with our 24/7 dispatch and tracking team while maintaining the freedom to ...

New

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Van Owner Operator

Milwaukee, WI · On-site

$3.5K - $5.0K/wk

We provide freight opportunities for Sprinter Vans and Straight Trucks, with local, regional, and ... Owner-operators work with our 24/7 dispatch and tracking team while maintaining the freedom to ...

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Local Owner Operator Trucking information

See Wisconsin salary details

$650

$4.4K

$7.8K

How much do local owner operator trucking jobs pay per week?

As of Aug 23, 2026, the average weekly pay for local owner operator trucking in Wisconsin is $4,436.79, according to ZipRecruiter salary data. Most workers in this role earn between $2,426.92 and $6,600.00 per week, depending on experience, location, and employer.

What is a local owner operator in trucking?

A local owner operator in trucking is an individual who owns and operates their own commercial truck and contracts with companies or shippers to transport goods within a specific local or regional area. Unlike company drivers, owner operators are independent contractors responsible for maintaining their vehicle, managing their business operations, and handling expenses such as fuel, insurance, and repairs. Their work typically involves shorter routes, allowing them to return home daily or nightly, which can provide a better work-life balance compared to long-haul trucking.

What are the key skills and qualifications needed to thrive as a local owner operator in trucking?

To thrive as a Local Owner Operator Trucking professional, you need a valid commercial driver's license (CDL), safe driving record, and a solid understanding of logistics and route planning. Familiarity with GPS navigation systems, electronic logging devices (ELDs), and basic truck maintenance tools is typically required. Strong time management, self-motivation, and customer service skills help you stand out in this role. These skills ensure efficient deliveries, regulatory compliance, customer satisfaction, and the profitability of your independent trucking business.

What are the typical challenges faced by local owner operator truck drivers, and how can they successfully manage them?

Local owner operator truck drivers often face challenges such as managing their own business expenses, securing consistent loads, and handling vehicle maintenance. Unlike company drivers, owner operators are responsible for their own insurance, fuel costs, and regulatory compliance, which requires strong organizational skills. Building relationships with reliable freight brokers and shippers, staying proactive with preventive maintenance, and keeping detailed records can help manage these challenges effectively. Additionally, networking with other local drivers and joining industry associations can provide valuable support and business opportunities.

What is the difference between Local Owner Operator Trucking vs Local Company Driver?

AspectLocal Owner Operator TruckingLocal Company Driver
CredentialsCommercial Driver's License (CDL), business license (if applicable)CDL, no business licensing needed
Work EnvironmentOperate own truck, flexible routes, independentDrive company-owned trucks, supervised by employer
Employer & Industry UsageSelf-employed, contracts with carriersEmployed directly by trucking companies
Search & Comparison IntentHigh overlap, both involve local freight delivery

In summary, Local Owner Operator Trucking involves operating your own truck independently, often with business responsibilities, while a Local Company Driver works for a trucking company using their equipment. Both roles require a CDL and involve local deliveries, but differ in ownership, independence, and employment structure.

How much do local owner operator truckers make?

Local owner operator truckers typically earn between $100,000 and $200,000 annually, depending on factors such as experience, routes, and freight volume. They are responsible for managing their own schedules, expenses, and equipment maintenance, which can impact their overall income.

What are popular job titles related to Local Owner Operator Trucking jobs in Wisconsin?

For Local Owner Operator Trucking jobs in Wisconsin, the most frequently searched job titles are:

What job categories do people searching Local Owner Operator Trucking jobs in Wisconsin look for?

The top searched job categories for Local Owner Operator Trucking jobs in Wisconsin are:

What cities in Wisconsin are hiring for Local Owner Operator Trucking jobs?

Cities in Wisconsin with the most Local Owner Operator Trucking job openings:

Infographic showing various Local Owner Operator Trucking job openings in Wisconsin as of August 2026, with employment types broken down into 1% As Needed, 71% Full Time, 25% Part Time, and 3% Contract. Highlights an 97% Physical, 1% Hybrid, and 2% Remote job distribution, with an average salary of $230,713 per year, or $110.9 per hour.

Owner Operator driver

METRO TRANS LOGISTICS LLC

Milwaukee, WI • On-site

$3.5K - $5.0K/wk

Contractor

Posted 2 days ago

New

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Job description

Metro Trans Logistics LLC is hiring Owner-Operators with their own Sprinter Van or Straight Truck.

Average Gross Revenue: $3,000–$4,000 per week
Actual earnings depend on vehicle type, availability, miles, and load volume.

What We Offer:

  • No forced dispatch
  • Local, regional, and OTR opportunities
  • Weekly settlements via direct deposit
  • QuickPay option available
  • 24/7 dispatch and tracking support
  • Consistent freight opportunities
  • Choose the loads and routes that work for you

Vehicle Requirements:

  • Sprinter Van – 2012 or newer
  • Straight Truck – 2009 or newer
  • Straight trucks must have a liftgate
  • Vehicle must be owned or financed and registered in your name
  • No rental or leased vehicles

Position Type: Independent Contractor / 1099 Owner-Operator

If you own the required equipment and are ready to run, apply today to start the onboarding process with Metro Trans Logistics LLC.

Company Description

Metro Trans Logistics LLC is a transportation and logistics company working with independent owner-operators across the United States. We provide freight opportunities for Sprinter Vans and Straight Trucks, with local, regional, and OTR options available.

Our focus is on reliable communication, flexible dispatch, and consistent support for our contractors. Owner-operators work with our 24/7 dispatch and tracking team while maintaining the freedom to choose the loads and routes that fit their availability.

We offer weekly settlements, QuickPay options, no forced dispatch, and ongoing freight opportunities for qualified owner-operators.