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Contractor Connection Jobs in Chicago, IL (NOW HIRING)

CONNECTION

IT Specialist/AI Tech

Downers Grove, IL

Overview Connection has a fantastic opportunity through our Technical Staffing division for an ... This is an excellent opportunity to join a growing organization offering competitive contractor ...

Connection

IT Specialist/AI Tech

Downers Grove, IL

Connection has a fantastic opportunity through our Technical Staffing division for an IT Specialist ... This is an excellent opportunity to join a growing organization offering competitive contractor ...

Connection

IT Specialist/AI Tech

Downers Grove, IL · On-site

Overview Connection has a fantastic opportunity through our Technical Staffing division for an ... This is an excellent opportunity to join a growing organization offering competitive contractor ...

Connection

IT Specialist/AI Tech

Downers Grove, IL

Overview Connection has a fantastic opportunity through our Technical Staffing division for an ... This is an excellent opportunity to join a growing organization offering competitive contractor ...

CONNECTION

IT Specialist/AI Tech

Downers Grove, IL

Overview Connection has a fantastic opportunity through our Technical Staffing division for an ... This is an excellent opportunity to join a growing organization offering competitive contractor ...

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Contractor Connection information

See Chicago, IL salary details

$10

$56

$81

How much do contractor connection jobs pay per hour?

As of Aug 9, 2026, the average hourly pay for contractor connection in Chicago, IL is $56.64, according to ZipRecruiter salary data. Most workers in this role earn between $44.33 and $70.82 per hour, depending on experience, location, and employer.

What is a Contractor Connection?

A Contractor Connection job typically involves coordinating and managing a network of contractors to handle property repairs, renovations, or insurance claims. Professionals in this role ensure quality service, compliance with industry standards, and efficient project completion. They may work with homeowners, insurers, and contractors to facilitate seamless project execution. The role often requires strong communication, organization, and problem-solving skills.

What are the key skills and qualifications needed to thrive in the Contractor Connection position, and why are they important?

To excel as a Contractor Connection, you need strong project coordination skills, knowledge of contracting processes, and experience in vendor management, often supported by a background in construction management or business administration. Familiarity with contractor management platforms, CRM systems, and relevant compliance or safety certifications is highly beneficial. Exceptional organizational skills, effective communication, and problem-solving abilities set outstanding professionals apart in this role. These competencies ensure efficient management of contractor relationships and successful completion of projects to client standards.

What does a Contractor Connection do?

A typical day in a Contractor Connection role involves managing the onboarding and communication between contractors and clients, reviewing work orders, and ensuring all project milestones are met on schedule. You will often coordinate with both internal teams and external vendors to resolve issues, facilitate compliance checks, and track progress through dedicated software systems. Additionally, you'll be responsible for maintaining documentation and updating stakeholders on project statuses. This role is highly collaborative and requires effective multitasking to ensure project quality and client satisfaction.

What are the most commonly searched types of Contractor Connection jobs in Chicago, IL? The most popular types of Contractor Connection jobs in Chicago, IL are:
What are popular job titles related to Contractor Connection jobs in Chicago, IL? For Contractor Connection jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Contractor Connection jobs in Chicago, IL look for? The top searched job categories for Contractor Connection jobs in Chicago, IL are:
Contractor Connection jobs near you
Infographic showing various Contractor Connection job openings in Chicago, IL as of July 2026, with employment types broken down into 60% Full Time, 10% Part Time, and 30% Contract. Highlights an 75% In-person, and 25% Remote job distribution, with an average salary of $117,819 per year, or $56.6 per hour.

IT Specialist (AI & Desktop Support)

Connection

Downers Grove, IL • On-site

$27.88 - $31.25/hr

Full-time

Medical, Dental, Vision, Life, Retirement

Posted 17 days ago

Job description

Connection has a fantastic opportunity through our Technical Staffing division for an IT Specialist supporting our client in Downers Grove, IL. This is an excellent opportunity to join a growing organization offering competitive contractor benefits with the potential to convert to a full-time employee. Once hired permanently, employees receive an excellent benefits package including 3 weeks of paid PTO, tuition reimbursement, 401(k), comprehensive medical, dental, and vision coverage, and outstanding career growth opportunities.


This is an onsite position located in Downers Grove, IL (60515) working Monday through Friday, 8:00 AM – 5:00 PM. There is no travel required.


Contract-to-Hire
Permanent Salary: Comparable to contract compensation

Position Overview


We are seeking an IT Specialist who has a solid foundation in desktop support and a genuine interest in expanding their knowledge of Artificial Intelligence technologies. This is an exciting opportunity for someone who enjoys traditional IT support while also wanting hands-on exposure to emerging AI tools and initiatives.


This position is ideal for someone who is naturally curious about AI and wants to grow into a more AI-focused role over time.


AI Responsibilities (Approximately 40%)

  • Utilize and explore AI platforms such as Microsoft Copilot, ChatGPT, Gemini, or similar generative AI tools.
  • Assist with AI initiatives and process improvements across the organization.
  • Help develop, configure, or test AI agents or AI-powered workflows.
  • Support experimentation with AI chatbots, automation, AI-generated content, and related technologies.
  • Stay current on emerging AI trends and recommend new opportunities for improving business processes.
  • Collaborate with internal teams to identify practical AI use cases.

IT Support Responsibilities (Approximately 60%)

  • Provide desktop and end-user support by resolving service desk tickets.
  • Configure and deploy desktop and laptop computers.
  • Create, modify, and maintain Active Directory user accounts and permissions.
  • Support Microsoft 365 / Office 365 users.
  • Troubleshoot desktop hardware, software, printers, and peripheral devices.
  • Perform PC inventory management, asset tracking, shipping, and receiving of equipment.
  • Follow documented procedures while managing multiple priorities.
  • Assist with general desktop support projects as needed.
  • Maintain excellent customer service and communication with end users.


Qualifications

  • 3+ years of IT support, desktop support, or help desk experience.
  • Experience supporting Active Directory and Microsoft 365 / Office 365 environments.
  • Strong troubleshooting and customer service skills.
  • Excellent verbal and written communication abilities.
  • Ability to multitask and follow established processes.
  • Interest in learning and growing within Artificial Intelligence technologies.
  • Experience using AI tools such as Copilot, ChatGPT, Gemini, or similar platforms.
  • Exposure to AI agents, chatbots, prompt engineering, or AI automation is highly preferred.
  • Self-motivated with a willingness to learn new technologies.


Physical Requirements


  • Ability to bend, lift, carry, and move equipment weighing up to 30 pounds.
  • Ability to transport computers and equipment using carts when necessary.


Preferred Qualifications


  • Experience creating or experimenting with AI agents or AI workflows.
  • Familiarity with AI image generation, AI bots, or business automation tools.
  • Previous experience working in a Windows desktop support environment.


Start Date: Immediate opening with the opportunity to start as soon as possible.

Company Description

Connection, a Fortune 1000 Global Solutions Provider, drives customer growth by calming the confusion of IT, guiding the connection between people and technology. The Connection brand includes Connection® Business Solutions, Connection® Enterprise Solutions, and Connection® Public Sector Solutions, which provide IT solutions and services to SMB, enterprise, and public sector markets. Connection holds hundreds of certifications with top vendors and offers expertise across multiple technology areas, delivering solutions to customers in over 174 countries.