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1099 Contractor Jobs in Chicago, IL (NOW HIRING)

DKD Logistics

Dispatcher (1099 Contractor)

Willowbrook, IL · On-site

$750 - $1.6K/wk

Classification: 1099 Independent Contractor Key Responsibilities * Schedule and dispatch drivers, vehicles, and loads based on customer needs and delivery timelines * Monitor routes and shipments to ...

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DKD Logistics

Dispatcher (1099 Contractor)

Burr Ridge, IL · On-site

$750 - $1.6K/wk

Classification: 1099 Independent Contractor Key Responsibilities * Schedule and dispatch drivers, vehicles, and loads based on customer needs and delivery timelines * Monitor routes and shipments to ...

RidenRoll

1099 Contractor Drivers

Chicago, IL · On-site

W-9 form for 1099 contractors * Comfortable using GPS navigation apps. Vehicle Requirements: * Less than 10 years old. * 4 doors * 5-8 seats, including the drivers. * Local State license plate ...

RidenRoll

RideShare RidenRoll App Drivers

Chicago, IL · On-site

$19.50 - $26.50/hr

RidenRoll.com is a California-based, for-profit technologies app platform to connect users, 1099 contractor Ride-Hauling drivers, and 1099 contractor delivery drivers to provide all essential ...

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All Jobs1099 Contractor Jobs1099 Contractor Jobs in Chicago, IL

1099 Contractor information

See Chicago, IL salary details

$10

$38

$102

How much do 1099 contractor jobs pay per hour?

As of Sep 5, 2026, the average hourly pay for 1099 contractor in Chicago, IL is $38.17, according to ZipRecruiter salary data. Most workers in this role earn between $20.48 and $43.42 per hour, depending on experience, location, and employer.

What is a 1099 contractor?

A 1099 Contractor is a self-employed individual or independent worker who provides services to a company under a contract, rather than as an employee. They are responsible for paying their own taxes, including self-employment tax, and do not receive benefits like health insurance or paid time off. Companies hire 1099 Contractors for short-term projects, freelance work, or specialized expertise. This type of work offers flexibility but requires managing business expenses and tax obligations independently.

What are some common challenges 1099 contractors face, and how can they overcome them?

As a 1099 Contractor, you may face challenges such as fluctuating workloads, managing multiple client expectations, and keeping track of tax obligations independently. Building strong organizational habits, clear communication with clients, and diligent record-keeping can help you address these issues effectively. Many successful contractors use project management tools and accounting software to stay on top of deadlines and finances. Joining industry networks and continuously upgrading your skills can also provide stability and growth opportunities in a competitive market.

What are the key skills and qualifications needed to thrive as a 1099 contractor, and why are they important?

To thrive as a 1099 Contractor, you need strong expertise in your professional field, solid self-management skills, and a clear understanding of independent contractor requirements. Familiarity with invoicing systems, contract management tools, and accounting software is often necessary, and some contractors may benefit from certifications in their specialty. Excellent communication, time management, and adaptability help contractors effectively manage client relationships and multiple projects. These skills ensure independent contractors can efficiently deliver quality work, remain compliant, and sustain a successful freelance business.

How do I become a 1099 contractor?

To become a 1099 contractor, you typically need to identify a freelance or contract opportunity, complete any required applications or onboarding processes, and set up your own business structure such as a sole proprietorship or LLC. You will also need to obtain any necessary licenses or certifications, and manage your taxes independently since 1099 contractors are responsible for their own tax payments. Having skills relevant to the work and a reliable method of invoicing or payment processing are also important.

How much does a 1099 contractor make?

The earnings of a 1099 contractor vary widely depending on the industry, experience, location, and the type of work performed. Contractors often set their own rates, which can range from $15 to over $100 per hour, and may earn more with specialized skills or certifications. Total income depends on the number of projects completed and hours worked, with some contractors earning six-figure annual incomes.

Is working as a 1099 contractor worth it?

Working as a 1099 contractor offers flexibility and the potential for higher pay, but it also means managing your own taxes, benefits, and job security. Contractors typically have more control over their schedule but lack employer-provided benefits like health insurance and retirement plans. Evaluating personal priorities and financial stability is important when considering this work arrangement.

What are the most commonly searched types of 1099 Contractor jobs in Chicago, IL?

The most popular types of 1099 Contractor jobs in Chicago, IL are:

What are popular job titles related to 1099 Contractor jobs in Chicago, IL?

For 1099 Contractor jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching 1099 Contractor jobs in Chicago, IL look for?

The top searched job categories for 1099 Contractor jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for 1099 Contractor jobs?

Cities near Chicago, IL with the most 1099 Contractor job openings:

1099 Contractor jobs near you
Infographic showing various 1099 Contractor job openings in Chicago, IL as of August 2026, with employment types broken down into 43% Full Time, 11% Part Time, and 46% Contract. Highlights an 83% In-person, and 17% Remote job distribution, with an average salary of $79,393 per year, or $38.2 per hour.

Dispatcher (1099 Contractor)

GTS Transportation

Burr Ridge, IL • On-site

$750 - $1.7K/wk

Full-time

Medical, Retirement

Re-posted 17 days ago

Job description

GTS Transportation, is a Chicagoland carrier specializing in dry-van, refrigerated, flatbed, expedited, and oversize freight logistics. We're looking for a Transportation Dispatcher to coordinate drivers, vehicles, and shipments, and serve as the key point of communication between drivers, customers, and internal teams. This role is based on-site at our Burr Ridge headquarters.
  • Location: 7545 S Madison St, Burr Ridge, IL 60527
  • Schedule: Monday-Friday, standard business hours (CDT)
  • Classification: 1099 Independent Contractor

Key Responsibilities
  • Schedule and dispatch drivers, vehicles, and loads based on customer needs and delivery timelines
  • Monitor routes and shipments to ensure on-time pickups and deliveries
  • Communicate with drivers on routes, delays, weather, and customer instructions
  • Ensure compliance with DOT/FMCSA regulations, including Hours of Service (HOS)
  • Manage operations using dispatch software, GPS, and TMS platforms
  • Troubleshoot delays, breakdowns, or route changes with quick, effective solutions
  • Maintain accurate dispatch records, driver logs, and delivery confirmations
  • Coordinate with warehouse, operations, and customer service teams
  • Keep clients updated on shipment status
  • Review and optimize routes for efficiency and cost savings

Qualifications
  • High School Diploma or GED required
  • 1-2 years of dispatching experience in a carrier, broker, or transportation environment
  • Working knowledge of DOT/FMCSA regulations, including Hours of Service
  • Strong communication, problem-solving, and organizational skills
  • Ability to multitask and stay calm under pressure in a fast-paced environment
  • Proficiency with dispatch software, GPS/TMS systems, and general computer applications

Preferred
  • Experience in dry-van, refrigerated, flatbed, or expedited freight a huge plus
  • Familiarity with route optimization tools
  • Bilingual (Lithuanian, Ukrainian, or Russian) a huge plus

Compensation
This is a 1099 contractor position with pay ranging from $750-$1,700 per week, based on skills, experience, and qualifications. As a 1099 role, this position does not include employee benefits (health insurance, 401(k), etc).
GTS Transportation selects contractors without regard to race, color, religion, sex, national origin, age, disability, genetic information, or any other status protected by federal, state, or local law.

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