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Remote Windows System Administrator Jobs in Illinois

SA Technologies Inc.

Network Engineer

Bloomington, IL · Remote

... as a system administrator. The technical skills include the ability to install, support and ... Control and direct test efforts of employees at remote sites when applicable. Maintain and update ...

Elase Nationwide

Business System Manager

Wheaton, IL · On-site +1

$65 - $100K/hr

Bachelor's degree required * 2+ years as a systems admin required * POS experience and proficiency ... This position is remote and you must live in one of the states we currently operate in. CO, ID, AZ ...

Humana

Senior Systems Engineer

Chicago, IL · On-site +1

$107K - $147K/yr

Location Remote Candidates must be located in one of the following markets: Louisville, KY ... Design, implement, and maintain Windows and Linux server infrastructure. * Administer ...

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All JobsWindows System Administrator JobsRemote Windows System Administrator JobsRemote Windows System Administrator Jobs in Illinois

Remote Windows System Administrator information

See Illinois salary details

$52.3K

$93K

$126.5K

How much do remote windows system administrator jobs pay per year?

As of Sep 5, 2026, the average yearly pay for remote windows system administrator in Illinois is $92,984.00, according to ZipRecruiter salary data. Most workers in this role earn between $76,600.00 and $107,100.00 per year, depending on experience, location, and employer.

What is a remote Windows system administrator?

A Remote Windows System Administrator is an IT professional responsible for managing, configuring, and maintaining Windows-based servers and systems from a remote location. Their duties include monitoring system performance, applying updates and patches, troubleshooting technical issues, and ensuring the security and reliability of Windows environments across an organization. They often use remote access tools to perform their tasks, helping organizations maintain efficient and secure IT operations without being physically present on-site.

What are the key skills and qualifications needed to thrive as a remote Windows system administrator?

To thrive as a Remote Windows System Administrator, you need expertise in Windows Server administration, Active Directory, network protocols, and typically a degree in IT or related certifications like Microsoft Certified: Windows Server or Azure Administrator. Familiarity with tools such as PowerShell, Remote Desktop Services, VMware, and monitoring platforms is essential for managing and troubleshooting systems remotely. Excellent problem-solving, communication, and time-management skills help you to efficiently address issues and collaborate with distributed teams. These competencies ensure system reliability, security, and fast resolution of technical challenges in a remote environment.

What are some common challenges faced by remote Windows system administrators and how can they be addressed?

Remote Windows System Administrators often face challenges such as ensuring secure remote access, coordinating with geographically dispersed teams, and promptly resolving issues without on-site presence. To address these, effective communication tools, robust security protocols (like VPNs and multi-factor authentication), and proactive monitoring solutions are essential. Building strong documentation practices and maintaining regular updates with team members can also help manage tasks efficiently and ensure smooth operations.

What is the difference between Remote Windows System Administrator vs Remote Network Administrator?

AspectRemote Windows System AdministratorRemote Network Administrator
CertificationsMicrosoft Certified: Windows Server, CompTIA Network+Cisco CCNA, CompTIA Network+
Work EnvironmentManaging Windows servers, Active Directory, and server infrastructureManaging network hardware, routers, switches, and network security
Employer & Industry UsageIT departments across various industries focusing on Windows environmentsOrganizations needing network infrastructure management across industries

Remote Windows System Administrators primarily focus on managing Windows server environments, Active Directory, and related infrastructure. In contrast, Remote Network Administrators concentrate on network hardware, routing, switching, and network security. While both roles require networking certifications like CompTIA Network+ or Cisco CCNA, their daily tasks and focus areas differ significantly, catering to different aspects of IT infrastructure management.

What are popular job titles related to Remote Windows System Administrator jobs in Illinois?

For Remote Windows System Administrator jobs in Illinois, the most frequently searched job titles are:

What job categories do people searching Remote Windows System Administrator jobs in Illinois look for?

The top searched job categories for Remote Windows System Administrator jobs in Illinois are:

What cities in Illinois are hiring for Remote Windows System Administrator jobs?

Cities in Illinois with the most Remote Windows System Administrator job openings:

Remote Windows System Administrator jobs near you
Infographic showing various Remote Windows System Administrator job openings in Illinois as of August 2026, with employment types broken down into 1% As Needed, 80% Full Time, 17% Part Time, and 2% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $92,984 per year, or $44.7 per hour.

Technical IT Support Specialist - Chicago, IL

Buckeye Mountain

Chicago, IL • Remote

Full-time

Re-posted 8 days ago

Job description

The Role

We are looking for a technically minded IT support professional who can bridge the gap between end-user helpdesk and senior engineering. You are not a traditional help desk — you understand systems well enough to triage a network issue, interpret a monitoring alert, and know whether to resolve it yourself or get the right engineer involved. You will own monitoring across our network, cloud, and NaaS environments, serve as the first-level escalation for technical issues, and support endpoint and device management operations. When something is wrong somewhere in our environment, you will often be the first to know.

What You'll Own

Monitoring & Observability

• Monitor network, cloud, and NaaS environments using observability and alerting platforms — Splunk, cloud monitoring consoles, and remote management tools

• Own NaaS site monitoring — track link health, power telemetry, and connectivity status for all active remote sites

• Respond to and triage monitoring alerts; resolve within your scope or escalate with full context to the appropriate engineer

• Manage NaaS firmware and configuration changes for live sites in coordination with the Field Engineering team

Technical First-Level Support

• Serve as the first technical escalation point for issues routed up from the helpdesk — network connectivity, application access, system performance

• Perform first-level network troubleshooting — diagnosing issues before escalating to the Senior Network Engineer

• Own the technical ticket queue for infrastructure-adjacent issues, ensuring nothing sits unrouted

• Contribute to SLA compliance by maintaining response time discipline and clear ticket documentation

Endpoint & Device Support

• Assist the Identity & Endpoint Systems Administrator with device enrollment (Intune, Apple Business Manager), compliance policy deployment, and device imaging

• Support OS patching cycles for Windows and Linux systems under direction of the Systems & Application Engineer

• Contribute to knowledge base and troubleshooting documentation for recurring issues

What We're Looking For

Required

• 3+ years in an IT support, NOC, or junior systems administration role

• Working knowledge of networking concepts — TCP/IP, DNS, VLANs, subnetting, basic firewall behavior

• Experience with monitoring and alerting platforms — Splunk, PRTG, Datadog, Zabbix, or equivalent

• Familiarity with Microsoft Intune or another MDM platform for device enrollment and policy deployment

• Experience supporting Windows environments at a systems level — not just end-user troubleshooting

• Strong communication skills — ability to escalate clearly, document concisely, and keep stakeholders informed during incidents

• Experience with a ticketing platform (Jira Service Management preferred)

Preferred

• Experience monitoring or supporting remote or field-deployed network infrastructure

• NaaS, managed connectivity, ISP, or telecom support background

• Splunk experience — dashboards, searches, alert configuration

• Basic scripting ability — PowerShell or Python for automation or log parsing

• Linux command-line proficiency at a support level

Details

• Location: Remote — must be available during core US business hours

• Travel: Minimal

• Employment type: Full-time