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Remote Contractor Jobs in Chicago, IL (NOW HIRING)

BIA Group

Freight Contractor

Mount Prospect, IL · Remote

$1.0K - $1M/yr

BIA Group LLC is seeking an experienced Freight Contractor to secure high-value contracts in a remote, commission-based role. This is an exciting opportunity to work with a fast-growing company ...

Conifer

Design Researcher - Contractor

Chicago, IL · On-site +1

We are currently looking to hire on a project/contractor basis. ABOUT CONIFER Conifer Research ... Execute research programs drawing from established methodologies for ethnography, remote research ...

Liveops

Remote Customer Service Agent

Hammond, IN · Remote

$15 - $20/hr

Customer Service Agent -- Independent Contractor (Remote) Location: Remote (US-Based) Liveops is seeking independent contractors to provide virtual customer service support for a variety of client ...

Liveops

Remote Customer Service Agent

Crown Point, IN · Remote

$14.75 - $19.75/hr

Customer Service Agent -- Independent Contractor (Remote) Location: Remote (US-Based) Liveops is seeking independent contractors to provide virtual customer service support for a variety of client ...

Liveops

Remote Customer Service Agent

Gary, IN · Remote

$15.50 - $20.75/hr

Customer Service Agent -- Independent Contractor (Remote) Location: Remote (US-Based) Liveops is seeking independent contractors to provide virtual customer service support for a variety of client ...

Anderson Johnson Agency

Remote Insurance Agent

Joliet, IL · Remote

$60K - $120K/yr

Position Type: 1099 Independent Contractor * Compensation: Commission-based; earnings vary by activity and performance * Schedule: Flexible, remote; part-time or full-time * Location: Remote, United ...

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All JobsContractor JobsRemote Contractor JobsRemote Contractor Jobs in Chicago, IL

Remote Contractor information

See Chicago, IL salary details

$17

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How much do remote contractor jobs pay per hour?

As of Jul 20, 2026, the average hourly pay for remote contractor in Chicago, IL is $22.15, according to ZipRecruiter salary data. Most workers in this role earn between $18.56 and $23.51 per hour, depending on experience, location, and employer.

What is the difference between Remote Contractor vs Remote Freelancer?

AspectRemote ContractorRemote Freelancer
CredentialsOften requires specific certifications or industry experienceMay have varied credentials, often self-taught or with informal skills
Work EnvironmentTypically works for a single employer or client on a contractual basisWorks independently on multiple projects for different clients
Employer UsageCommonly hired through agencies or direct contracts for ongoing workHired directly by clients for short-term or one-off projects
Search & Comparison IntentOften compared for long-term project work or contractual rolesCompared for flexible, project-based work opportunities

Remote Contractors usually work for a single employer under a formal contract, often requiring specific credentials. Freelancers work independently across multiple clients, offering flexibility but less long-term stability. Both roles are popular in remote work, but they differ in work structure and employer relationships.

How to make $70,000 a year from home?

A remote contractor can reach a $70,000 annual income by developing specialized skills such as programming, digital marketing, or graphic design, and building a strong portfolio. Consistently applying for high-paying freelance projects, maintaining a professional online presence, and managing multiple clients can help achieve this income level.

Can contractors work remotely?

Remote contractors can work from any location with internet access, depending on the employer’s policies and the nature of the work. Many remote contracting roles require skills in communication tools and project management software, and some may have specific location or time zone requirements.

What are remote contractors?

Remote contractors are independent professionals or freelancers who work for companies or clients from a location outside of the traditional office setting, often from their own home or a co-working space. They are typically hired for specific projects or tasks and are not considered employees, which means they manage their own taxes, benefits, and work schedule. Remote contractors use digital communication tools to collaborate with teams and deliver results across a variety of industries, such as IT, marketing, writing, and design. This arrangement provides flexibility for both the contractor and the hiring company.

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

To thrive as a Remote Contractor, strong time management, self-motivation, and relevant domain expertise are essential, often supported by proven experience or industry-specific credentials. Familiarity with collaboration tools like Slack, Zoom, and project management platforms such as Asana or Trello is typically required. Excellent written communication, adaptability, and problem-solving skills help remote contractors stand out in virtual environments. These skills and qualities ensure productivity, reliability, and effective collaboration when working independently from various locations.

How does communication typically work for remote contractors collaborating with distributed teams?

Remote contractors usually communicate with their teams via digital platforms such as Slack, Microsoft Teams, or Zoom. It is common to participate in regular virtual meetings, submit progress updates, and coordinate tasks through project management tools. Since contractors often work across time zones, clear and timely communication is essential to stay aligned with team goals and project deadlines. Being proactive in sharing your availability and progress helps ensure smooth collaboration and fosters trust within the team.

How to make $1000 a week remotely?

A remote contractor can earn $1000 a week by taking on multiple freelance or contract projects that pay well, such as in writing, programming, design, or digital marketing. Building a strong skill set, maintaining a professional portfolio, and using platforms like Upwork or Freelancer can help secure higher-paying assignments and increase weekly income.

What jobs pay 4000 a week without a degree?

Remote contractors in fields like software development, digital marketing, or consulting can earn $4,000 or more weekly without a degree, often based on experience, skills, and project scope. High-paying freelance roles typically require strong expertise, a solid portfolio, and proficiency with relevant tools or platforms. Such positions may involve project-based work, client management, and self-motivation.
What are the most commonly searched types of Contractor jobs in Chicago, IL? The most popular types of Contractor jobs in Chicago, IL are:
What are popular job titles related to Remote Contractor jobs in Chicago, IL? For Remote Contractor jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Contractor jobs in Chicago, IL look for? The top searched job categories for Remote Contractor jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Contractor jobs? Cities near Chicago, IL with the most Remote Contractor job openings:
Remote Contractor jobs near you
Infographic showing various Remote Contractor job openings in Chicago, IL as of July 2026, with employment types broken down into 73% Full Time, 10% Part Time, and 17% Contract. Highlights an 89% Physical, 1% Hybrid, and 10% Remote job distribution, with an average salary of $46,072 per year, or $22.1 per hour.

Digital Advertising Sales Reps - Remote Contractor Opportunity

Terraboost

Joliet, IL • Remote

$20K/mo

Other

Posted 17 days ago

Job description

Advertising Sales on Jumbo 5-Foot Ads at Major Retailers Amazing Opportunity for Independent Sales Contractors

High Earning Potential Total Flexibility Real Impact

This isnt just ad sales its the implied endorsement of major retailers like CVS, Kroger, HEB, and Albertsons. Youll offer clients prime front-door exposure on full-color, 5-foot-tall wellness kiosks the first message shoppers see as they walk in.

Join Terraboost Media as an Independent Sales Contractor and take full control of your income and schedule.

CLICK HERE TO WATCH A 2-MINUTE VIDEO WITH DETAILS ABOUT THE OPPORTUNITY!

Why Terraboost?

  • Unlimited Earning Potential Top reps earn UP TO $20,000+/month and up to $1,500 per contract
  • Total Flexibility Work remotely, set your own hours
  • Proven Support Tools, training, and expert guidance to help you close more deals
  • Optional Leads & Telemarketing Provided after proving results, or available sooner for a fee
  • Earn While You Train After completing training, earn $30 per qualified meeting you set (up to 5). Thats up to $150 right away and youll be joined by a seasoned Terraboost pro who helps present and close. If the deal closes, you earn the full commission (typically $800$1,500 per sale).

Who Were Looking For:

  • Experienced Sales Pros Ideally with advertising, marketing, or media background
  • Driven Closers Self-motivated, commission-focused, and results-driven
  • Proactive Prospectors Comfortable reaching out to local businesses and booking meetings
  • Or someone with grit and hunger ready to follow a proven playbook and win

Learn more at www.terraboost.com

Apply now and start selling something that truly stands out and get paid while learning how.

CLICK HERE TO WATCH A 2-MINUTE VIDEO WITH DETAILS ABOUT THE OPPORTUNITY!

Apply