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Remote Windows System Administrator Jobs in Chicago, IL

ECHO

IBM System Administrator

Lake Zurich, IL · On-site +1

$90K - $110K/yr

The IBM Power Systems Administrator / Operator is responsible for the administration, operation, maintenance, and support of ECHO's IBM Power infrastructure and IBM i (AS/400) environments. This role ...

Firstup

Senior Systems Administrator - Chicago

Chicago, IL · Remote

$125K - $140K/yr

As a fully remote role supporting a globally distributed workforce, this position owns and manages ... Monitor system health, performance, availability, and capacity, proactively identifying and ...

Firstup

Senior Systems Administrator - Chicago

Chicago, IL · Remote

$88K - $120K/yr

As a fully remote role supporting a globally distributed workforce, this position owns and manages ... Monitor system health, performance, availability, and capacity, proactively identifying and ...

Shure

Senior Systems Administrator

Niles, IL · On-site +1

$86K - $117K/yr

This role will lead key functions including Windows and Linux administration, SAN management, and ... Focus on optimizing system performance, scalability, and security across all platforms. * Manage ...

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All JobsWindows System Administrator JobsRemote Windows System Administrator JobsRemote Windows System Administrator Jobs in Chicago, IL

Remote Windows System Administrator information

See Chicago, IL salary details

$55.6K

$98.8K

$134.4K

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

As of Aug 7, 2026, the average yearly pay for remote windows system administrator in Chicago, IL is $98,849.00, according to ZipRecruiter salary data. Most workers in this role earn between $81,400.00 and $113,800.00 per year, depending on experience, location, and employer.

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 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 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 Chicago, IL? For Remote Windows System Administrator jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Windows System Administrator jobs in Chicago, IL look for? The top searched job categories for Remote Windows System Administrator jobs in Chicago, IL are:
Remote Windows System Administrator jobs near you
Infographic showing various Remote Windows System Administrator job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 83% Full Time, 13% Part Time, and 3% Contract. Highlights an 92% Physical, 2% Hybrid, and 6% Remote job distribution, with an average salary of $98,849 per year, or $47.5 per hour.

Senior Windows Administrator, Financial or Trading Experience Required - Work From Home

Next Step Systems

Chicago, IL • On-site, Remote

Full-time

Medical, Retirement, PTO

Re-posted yesterday

Job description

Senior Windows Administrator, Financial or Trading Experience Required - Work From Home
We are currently looking for a Senior Windows Administrator for a great work from home opportunity. We are seeking a talented and self-motivated Senior Windows Administrator to join a growing IT team. This position is 100% Remote.
Senior Windows Administrator Responsibilities:
- The Senior Windows Administrator will be added to an existing IT team where they will interact with all IT functional areas (e.g. architecture, design, network engineering, Helpdesk/Desktop support, application development and support).
- The Senior Windows Administrator will be working in a dynamic, heterogeneous environment and must have an extensive technical background including experience in troubleshooting, monitoring, maintenance and networking.
Senior Windows Administrator Qualifications:
- Bachelor's Degree from a 4-year university in computer science, information science or related technical field.
- Excellent written and verbal communication.
- Thorough knowledge (5+ years) of Windows architecture, deployment, administration, networking, performance monitoring/tuning, security hardening, troubleshooting and production operations.
- Thorough knowledge of Windows 7 and Windows 10 desktop operating systems.
- Highly organized, self-motivated, able to multi-task, able to work independently as well as a team player.
- Must be willing to work some weekend shifts in support of maintenance and participate in On-call for overnights, weekends and holidays on a rotational basis with openness to change duties.
- Must have operations experience in 24/7 environments.
- Must be knowledgeable about Active Directory and recent versions of Microsoft Exchange.
- Have familiarity with basic Linux commands and ability to assist in building and managing Linux systems.
- System configuration experience (SMS, Altiris, PowerShell).
- Experience supporting Citrix is a plus.
- System monitoring experience (SNMP, Dell Open Manage, etc.).
- Working knowledge of virtualization (Hyper-V, VMWare, etc.) is a plus.
- The ideal candidate will have worked within the financial industry with a robust background in Linux design, implementation and support.
- Must be highly self-motivated, excel at multitasking, and comfortable working in a demanding, state of the art trading environment.
- Employees must be legally authorized to work in the US.
- Work location in the US is generally flexible and subject to approval.
Benefits include medical insurance, retirement plan, PTO, etc. Salary: 80K+ DOE. Keywords: Chicago IL Jobs, Senior Windows Administrator, Windows, Windows 7, Windows 10, Active Directory, Microsoft Exchange, Linux, SMS, Altiris, PowerShell, SNMP, Dell Open Manage, Hyper-V, VmWare, Trading, Financial, Remote, Work From Home, Chicago Recruiters, Information Technology Jobs, IT Jobs, Chicago Recruiting
Looking to hire for similar positions in Chicago, IL or in other cities? Our IT recruiting agencies and staffing companies can help.
We help companies that are looking to hire Senior Windows Administrators for jobs in Chicago, Illinois and in other cities too. Please contact our IT recruiting agencies and IT staffing companies today! Phone 630-428-0600 ext. 11 or email us at jobs@nextstepsystems.com. Click here to submit your resume for this job and others.
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