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Virtual Help Desk Jobs in Chicago, IL (NOW HIRING)

Helpdesk Technician Company: Four Seasons Heating, Air Conditioning, Plumbing & Electric Location ... Experience supporting Windows Server and Linux virtual machines a plus. * Experience supporting ...

New

Help Desk Associate

Chicago, IL · On-site

$65K - $75K/yr

Helpdesk Technician Company: Four Seasons Heating, Air Conditioning, Plumbing & Electric Location ... Experience supporting Windows Server and Linux virtual machines a plus. * Experience supporting ...

New

Helpdesk Analyst

Chicago, IL

$24.38 - $28.04/hr

The Help Desk Analyst will have opportunities to develop systems administration skills in Microsoft ... FREE Virtual Primary Care, Urgent Care, and Mental Health Counseling for ALL Employees * PAID ...

Helpdesk Analyst

Skokie, IL

$24.38 - $28.04/hr

The Help Desk Analyst will have opportunities to develop systems administration skills in Microsoft ... FREE Virtual Primary Care, Urgent Care, and Mental Health Counseling for ALL Employees * PAID ...

Helpdesk Analyst

Chicago, IL · On-site

$24.38 - $28.04/hr

The Help Desk Analyst will have opportunities to develop systems administration skills in Microsoft ... FREE Virtual Primary Care, Urgent Care, and Mental Health Counseling for ALL Employees * PAID ...

Service Desk Analyst

Chicago, IL · Remote

$20 - $25/hr

The ideal candidate enjoys helping people, excels in a fast-paced environment, and possesses strong ... Provide support for virtual meetings, collaboration platforms, and video conferencing technologies.

Desktop Technician

Crystal Lake, IL · On-site

$19.75 - $25/hr

... virtual desktop, and mobile device hardware and peripherals. • Administer desktop patch ... according to help desk procedures. • Perform periodic help desk and instructional media ...

Front Desk/Admin Assistant

Carol Stream, IL · On-site

$16.25 - $20.75/hr

Front Desk/Admin Assistant QPS Employment Group is hiring a Front Desk/Admin Assistant for a 12 ... Please note that QPS Employment Group may use a virtual recruiting assistant to help screen and ...

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Virtual Help Desk information

See Chicago, IL salary details

$13

$23

$34

How much do virtual help desk jobs pay per hour?

As of Aug 21, 2026, the average hourly pay for virtual help desk 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 virtual help desk?

Virtual help desk jobs involve providing technical support and assistance to customers or employees remotely, often via phone, email, or chat. Professionals in these roles troubleshoot software, hardware, and network issues, guide users through problem-solving steps, and escalate complex issues as needed. They play a crucial role in maintaining smooth IT operations for organizations by resolving issues quickly and efficiently from a remote location.

What are the key skills and qualifications needed to thrive as a virtual help desk professional?

To thrive as a Virtual Help Desk professional, you need strong problem-solving abilities, technical troubleshooting skills, and a solid understanding of computer systems and networks, often supported by a relevant IT certification like CompTIA A+ or Microsoft Certified: Modern Desktop Administrator Associate. Familiarity with remote support tools, ticketing systems such as Zendesk or ServiceNow, and knowledge base platforms is typically required. Excellent communication, patience, and customer service orientation are vital soft skills for effectively assisting users and managing stressful situations. These skills and qualities ensure efficient, accurate support for end-users and contribute to high customer satisfaction in a remote environment.

What are some common challenges faced by virtual help desk professionals, and how can they be addressed?

Virtual Help Desk professionals often encounter challenges such as managing high volumes of support requests, communicating clearly with users remotely, and troubleshooting issues without physical access to devices. To address these, it's important to prioritize tickets effectively, utilize remote access tools, and develop strong written and verbal communication skills. Additionally, ongoing training in the latest support technologies and regular collaboration with team members can help overcome these challenges and ensure excellent service delivery.

What is the difference between Virtual Help Desk vs Technical Support Specialist?

AspectVirtual Help DeskTechnical Support Specialist
Required CredentialsHigh school diploma or equivalent; certifications like CompTIA A+High school diploma; certifications like CompTIA A+ or Network+
Work EnvironmentRemote, customer service-focusedRemote or on-site, technical troubleshooting
Employer & Industry UsageIT service providers, tech companies, MSPsIT companies, tech support firms, hardware vendors

The Virtual Help Desk and Technical Support Specialist roles both require technical knowledge and certifications like CompTIA A+. The main difference lies in their focus: Virtual Help Desk roles emphasize customer service and remote support, while Technical Support Specialists often handle more technical troubleshooting and hardware issues. Both roles are essential in IT support environments and often overlap in skills and certifications.

What are the most commonly searched types of Help Desk jobs in Chicago, IL?

The most popular types of Help Desk jobs in Chicago, IL are:

Infographic showing various Virtual Help Desk job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 71% Full Time, 24% Part Time, and 4% Contract. Highlights an 86% Physical, 2% Hybrid, and 12% Remote job distribution, with an average salary of $49,605 per year, or $23.8 per hour.

$65K - $75K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 2 days ago

New


Job description

Job Title: Helpdesk Technician

Company: Four Seasons Heating, Air Conditioning, Plumbing & Electric

Location: Bedford Park, IL

Pay: $65k-$75k

About Us

Four Seasons Heating and Cooling is Chicagoland’s leading provider of HVAC, electrical, plumbing, duct cleaning, and backup generator services.  We are committed to delivering exceptional service to our customers by equipping our back-office and field teams with exceptional technology support, ensuring they have the necessary tools for success. We are currently seeking a skilled and motivated Helpdesk Technician to join our IT team and support our fast-paced and rapidly growing company.

Job Responsibilities

  • Respond to employee support requests submitted via ticketing system (Jira), phone, email, Teams chat, and in-person visits.
  • Diagnose and resolve technical issues efficiently to minimize employee impact.
  • Track and manage support tickets using our case management system (Jira).
  • Maintain and troubleshoot office IT equipment, including mobile devices (Android), printers, video conferencing systems, wireless access points, etc.
  • Provide support for employee workstations and devices, including laptops, desktops, thin clients, monitors, docking stations, and peripherals. 
  • Facilitate employee onboarding and offboarding by setting up workspaces, including laptop/desktop, monitors, docking station, headset, mobile devices, and managing user accounts.
  • Provide support for a wide range of business applications, and Microsoft hybrid service environments.
  • Be an advocate for the helpdesk to advise employees on how to request support from the helpdesk.
  • Escalate complex issues to Level 3 support, if necessary.
  • Work shifted hours, as needed, to provide Helpdesk support to the company during the hours Monday-Friday 730a-6p CT. 
  • Be part of the Helpdesk after-hours support rotation to provide support for critical issues outside of normal business hours.
  • Occasionally report to other Four Seasons offices on a scheduled or as-needed basis to support employees or projects.

Job Requirements

  • This position requires daily attendance at our Bedford Park, IL office and is not eligible for hybrid work.  May require occasional travel to other offices.
  • Excellent communication and customer service skills are critical for this role.
  • Minimum 2 years of experience in an IT helpdesk support role.
  • Minimum 2 years of experience using a support case management system such as Jira or ServiceNow.
  • Deep knowledge troubleshooting and supporting Windows Operating system and Dell laptop and desktop computers. 
  • Significant experience managing users in Active Directory, Microsoft 365, and Azure Entra ID.
  • Experience supporting Android mobile. Familiarity with Samsung Knox mobile device management a plus.
  • Experience managing Windows laptop and desktop computers using Microsoft Intune.
  • Experience supporting Windows Server and Linux virtual machines a plus.
  • Experience supporting network devices such as wireless access points and switches a plus.
  • Strong organizational skills and attention to detail.
  • Ability to work independently and handle multiple tasks simultaneously.
  • Experience working for an HVAC, electrical, plumbing, managed service provider, or other service-oriented industries is a plus.
  • Must have reliable transportation.  Preference given to candidates with valid driver’s license and own vehicle.

Benefits

  • Medical Insurance (employer subsidized)
  • Accident Insurance
  • Critical Illness Insurance
  • Hospital Indemnity Insurance
  • Dental Insurance (free to employees)
  • Vision Insurance (free to employees)
  • Short-Term Disability (free to employees)
  • Long-Term Disability
  • Basic Life Insurance (free to employees)
  • Holiday Pay
  • Paid Time Off
  • 401(k) with matching
  • Credit Union
  • Cellular Discounts

Equal Opportunity & Reasonable Accommodation

Four Seasons is an affirmative action and equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, disability, age, sexual orientation, gender identity, national origin, veteran status, or genetic information. Four Seasons is committed to providing access, equal opportunity, and reasonable accommodation for individuals with disabilities. To request reasonable accommodation, contact Human Resources at 773-284-6161 Ext 5010.

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