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Remote It Helpdesk Jobs in Chicago, IL (NOW HIRING)

Sterling Engineering Inc.

Director of IT

Chicago, IL · On-site +1

Title : Director of IT - (Manufacturing and Industrial) Infrastructure and Delivery Location ... remote users. * Partner with operational technology teams to support secure IT/OT integration ...

Noor Locum

Diagnostic Radiologist

Tinley Park, IL · Remote

Integrated PACS and RIS * Remote IT support available during all shifts Qualifications * Board Certification in Diagnostic Radiology (ABR or AOBR) * Active Illinois medical license (or willingness to ...

Sralab

IT Security Analyst

Chicago, IL · Remote

... care to help patients achieve better, faster outcomes - as we Advance Human Ability, together ... Reporting Relationships Reports to Manager of IT Security Operations Remote work within the ...

Sentinel

IT Security Engineer

Downers Grove, IL · On-site +1

$70K - $100K/yr

This position can work remote within the United States and occasional travel to Downers Grove, IL required as needed. The IT Security Engineer will need excellent written and verbal communication ...

Sentinel

IT Security Engineer

Downers Grove, IL · On-site +1

$70K - $100K/yr

This position can work remote within the United States and occasional travel to Downers Grove, IL required as needed. The IT Security Engineer will need excellent written and verbal communication ...

Sentinel

IT Security Engineer

Downers Grove, IL · On-site +1

$70K - $100K/yr

This position can work remote within the United States and occasional travel to Downers Grove, IL required as needed. The IT Security Engineer will need excellent written and verbal communication ...

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All JobsIt Helpdesk JobsRemote It Helpdesk JobsRemote It Helpdesk Jobs in Chicago, IL

Remote It Helpdesk information

See Chicago, IL salary details

$13

$23

$34

How much do remote it helpdesk jobs pay per hour?

As of Aug 29, 2026, the average hourly pay for remote it helpdesk in Chicago, IL is $23.85, according to ZipRecruiter salary data. Most workers in this role earn between $19.81 and $26.73 per hour, depending on experience, location, and employer.

What is a remote IT helpdesk?

A Remote IT Helpdesk is a service or team that provides technical support to users from a distance, typically via phone, chat, or remote desktop tools. These professionals assist with troubleshooting computer issues, software problems, network connectivity, and other IT-related concerns without being physically present. Remote IT Helpdesk staff are essential for organizations with distributed workforces, ensuring employees have reliable access to technology and can resolve issues quickly. Their work helps minimize downtime and keep business operations running smoothly.

What are the key skills and qualifications needed to thrive as a remote IT helpdesk professional?

To thrive as a Remote IT Helpdesk professional, you need a solid understanding of computer systems, troubleshooting techniques, and customer support, often supported by a relevant IT degree or certifications like CompTIA A+ or Microsoft Certified: Modern Desktop Administrator Associate. Familiarity with ticketing systems (such as ServiceNow or Zendesk), remote desktop tools, and knowledge bases is typically required. Outstanding communication, patience, and problem-solving skills help you effectively resolve user issues and deliver excellent customer service remotely. These competencies ensure efficient technical support, minimize downtime, and enhance user satisfaction in distributed work environments.

What are some common challenges faced by remote IT helpdesk professionals and how can they be managed?

Remote IT Helpdesk professionals often encounter challenges such as troubleshooting issues without physical access to devices, communicating effectively with users of varying technical skills, and managing multiple support tickets simultaneously. To overcome these, it's important to develop strong remote diagnostic skills, use clear and patient communication, and leverage remote support tools efficiently. Staying organized and proactively documenting solutions can also help manage workload and ensure consistent service quality.

What is the difference between Remote It Helpdesk vs Remote Technical Support Specialist?

AspectRemote It HelpdeskRemote Technical Support Specialist
CertificationsCompTIA A+, Network+CompTIA A+, Cisco CCNA
Work EnvironmentHelpdesk ticketing systems, remote troubleshootingCustomer support, remote diagnostics, software/hardware issues
Industry UsageIT service providers, corporate IT departmentsIT support companies, tech vendors
Search IntentRemote IT Helpdesk vs Technical SupportRemote Technical Support vs Helpdesk

Remote It Helpdesk and Remote Technical Support Specialist roles share similarities in certifications and remote work environments. However, the Helpdesk typically focuses on ticket-based support for general IT issues, while Technical Support Specialists often handle more complex technical problems and may require additional certifications like Cisco CCNA. Both roles are vital in IT support, but they differ in scope and technical depth.

What are the most commonly searched types of It Helpdesk jobs in Chicago, IL?

The most popular types of It Helpdesk jobs in Chicago, IL are:

What are popular job titles related to Remote It Helpdesk jobs in Chicago, IL?

For Remote It Helpdesk jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote It Helpdesk jobs in Chicago, IL look for?

The top searched job categories for Remote It Helpdesk jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote It Helpdesk jobs?

Cities near Chicago, IL with the most Remote It Helpdesk job openings:

Remote It Helpdesk jobs near you
Infographic showing various Remote It Helpdesk job openings in Chicago, IL as of August 2026, with employment types broken down into 79% Full Time, 14% Part Time, and 7% Contract. Highlights an 100% Remote job distribution, with an average salary of $49,605 per year, or $23.8 per hour.

IT Specialist / Helpdesk Technician - Remote

Connection

Schaumburg, IL • On-site, Remote

Full-time

This job post has expired 2 days ago. Applications are no longer accepted.

Job description

Overview
Connection has a fantastic opportunity through our Technical Staffing division for a Technical Help Center IT Specialist. This is a contract to hire remote position with benefits.
Success in this role requires a positive attitude, strong customer service skills, curiosity, and a willingness to learn while supporting a fast-paced, nationwide organization.
Responsibilities
  • Provide Tier 1 and Tier 2 technical support for corporate team members and pet care centers nationwide.
  • Troubleshoot and resolve hardware, software, Windows, macOS, printer, network, phone, camera, and cloud service issues.
  • Manage and prioritize support requests through the IT ticketing system while delivering outstanding customer service.
  • Create and manage user accounts, permissions, and access within Okta, Active Directory, and Microsoft 365.
  • Configure, deploy, and support desktops, laptops, mobile devices, and related IT equipment.
  • Maintain accurate IT asset inventory and assist with equipment procurement and deployment.
  • Communicate project status and technical updates with team members and Technology staff.
  • Document solutions and contribute to technical knowledge resources.
  • Participate in an after-hours on-call rotation (currently approximately once every 6-8 weeks).

Qualifications
  • 2 - 5 years IT Help Desk experience supporting Windows / Office 365 Environments
  • Basic to intermediate understanding of networking and networking principles
  • Experience supporting macOS devices.
  • Nice to Haves - Zendesk experience, Okta experience, Azure or AWS experience
  • Enjoy communicating with and helping team members with a positive, friendly disposition
  • Great communication skills, ability to listen, empathize and communicate with team members over the phone or email
  • Learn quickly, self-starter, take direction well
  • Exceptional troubleshooting skills, detail orientated
  • Ability to manage multiple projects and meet deadlines.

Apply