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Remote Flatbed Owner Operator Jobs in Chicago, IL

Wanderlust Adventures

Remote Tourism Advisor

Chicago, IL · Remote

Company Description Our company is family owned and operated! We truly strive to keep an upbeat and ... Our company is looking for remote Tourism Advisors ! As a Tourism Advisor, you are responsible for ...

Wanderlust Adventures

Remote Tourism Advisor

Chicago, IL · On-site +1

Company Description Our company is family owned and operated! We truly strive to keep an upbeat and ... Our company is looking for remote Tourism Advisors! As a Tourism Advisor, you are responsible for ...

NAPAA

Allstate Insurance Sales - Remote

Oak Park, IL · On-site +1

$51K - $130K/yr

Salary Range: $51,000.00 - $130,000.00 per year This is a remote position. Compensation: $51,000.00 ... This agency is independently owned and operated. Your application will go directly to the agency ...

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All JobsFlatbed Owner Operator JobsRemote Flatbed Owner Operator JobsRemote Flatbed Owner Operator Jobs in Chicago, IL

Remote Flatbed Owner Operator information

See Chicago, IL salary details

$287

$5.8K

$7K

How much do remote flatbed owner operator jobs pay per week?

As of Aug 15, 2026, the average weekly pay for remote flatbed owner operator in Chicago, IL is $5,825.23, according to ZipRecruiter salary data. Most workers in this role earn between $4,646.15 and $6,934.62 per week, depending on experience, location, and employer.

What is a remote flatbed owner operator?

A Remote Flatbed Owner Operator is an independent truck driver who owns and operates their own flatbed truck and works remotely, often contracting with freight companies to transport various types of cargo. They are responsible for managing their own business operations, including scheduling, maintenance, and compliance with safety regulations. The 'remote' aspect typically refers to handling administrative tasks, bookings, and communication from any location, rather than being tied to a single office or terminal. This role offers flexibility and autonomy, but also requires strong organizational and business management skills.

What skills and qualifications are needed to thrive as a remote flatbed owner operator?

To thrive as a Remote Flatbed Owner Operator, you need a valid CDL, thorough knowledge of flatbed load securement, and experience with long-haul truck driving. Familiarity with electronic logging devices (ELDs), GPS systems, freight management software, and DOT safety regulations is essential. Strong self-motivation, time management, communication skills, and problem-solving abilities help you manage loads and client relationships independently. These competencies ensure safe, efficient transport and business success in a competitive logistics environment.

What is the difference between Remote Flatbed Owner Operator vs Remote Step Deck Owner Operator?

AspectRemote Flatbed Owner OperatorRemote Step Deck Owner Operator
CredentialsCommercial Driver's License (CDL), flatbed-specific trainingCDL, step deck/lowboy training
Work EnvironmentTransporting flatbed loads across regions, often requiring securement skillsHauling step deck/lowboy loads, often oversized or specialized equipment
Industry UsageCommon in construction, manufacturing, and freight industriesUsed for oversized or tall cargo, often in construction and heavy equipment sectors

Both Remote Flatbed Owner Operators and Remote Step Deck Owner Operators require CDL licenses and specialized training. Flatbed operators focus on transporting standard flat loads, while step deck operators handle taller, oversized cargo. The choice depends on the type of freight and industry specialization.

What are common challenges remote flatbed owner operators face, and how can they be managed?

Remote flatbed owner operators often encounter challenges related to route planning, securing consistent freight, and maintaining their equipment while on the road. Managing time efficiently and staying compliant with safety regulations can also be demanding, especially when operating independently. Building strong relationships with dispatchers and freight brokers, leveraging load boards, and investing in regular vehicle maintenance can help mitigate these challenges. Staying organized and proactive in communication are key to success in this role.

What are the most commonly searched types of Flatbed Owner Operator jobs in Chicago, IL?

The most popular types of Flatbed Owner Operator jobs in Chicago, IL are:

Remote Flatbed Owner Operator jobs near you
Infographic showing various Remote Flatbed Owner Operator job openings in Chicago, IL as of August 2026, with employment types broken down into 67% Full Time, and 33% Part Time. Highlights an 100% Remote job distribution, with an average salary of $302,912 per year, or $145.6 per hour.

Entry-Level Freight Dispatcher (Remote) - Earn $2,200 to $3,000 Weekly ($114,400-$156,000 Annually)

American Logistics Authority

Aurora, IL • On-site, Remote

$2.2K - $3.0K/wk

Full-time

Re-posted 29 days ago

Job description

Entry-Level Freight Dispatcher (Remote) - Earn $2,200 to $3,000 Weekly ($114,400-$156,000 Annually)
We are hiring motivated individuals to join our logistics team as Freight Dispatchers. This is a remote position with strong income potential. Candidates must already understand dispatching basics, know how to negotiate rates, be able to recruit owner-operators, and handle back-office support tasks.
Responsibilities:
  • Book freight through load boards and direct shippers
  • Negotiate rates with brokers and shippers to maximize profits
  • Schedule drivers, manage routes, and confirm delivery appointments
  • Provide full support to drivers while on the road
  • Handle back-office work: rate confirmations, carrier packets, invoicing, and compliance documents
  • Recruit and maintain relationships with qualified owner-operators

What We Offer:
  • Remote work from your home office
  • Weekly pay: $2,200-$3,000
  • Annual income potential: $114,400-$156,000
  • Training and ongoing support from experienced dispatchers
  • Long-term growth opportunities in the trucking industry

Qualifications:
  • Must be able to negotiate freight rates confidently
  • Experience with dispatching tasks (load boards, scheduling, paperwork)
  • Able to recruit and retain owner-operators
  • Comfortable handling back-office support tasks
  • Fluent in English (written and spoken)
  • Organized, detail-oriented, and strong at multitasking
  • Ready to start immediately
  • Serious inquiries only

Start your logistics career today with a six-figure income potential. Apply now to become a Freight Dispatcher.

Apply