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Windows Server Jobs in Chicago, IL (NOW HIRING)

Glow Networks

Architect RTP Stack

Chicago, IL · On-site

$68 - $87/hr

• Experience developing on and managing On-Prem Windows Server-based infrastructure. • Managing endpoints including point-of-sale devices running Windows OS, as well as their communication ...

TEKsystems c/o Allegis Group

Field Engineer

Chicago, IL · On-site

$50 - $52.50/hr

Windows Server and Hypervisor experience (VMware, Hyper-V, or similar virtualization platforms), including strong understanding of virtualization concepts, server deployments, and system ...

TEKsystems

Field Engineer

Chicago, IL

$50 - $52.50/hr

Windows Server and Hypervisor experience (VMware, Hyper-V, or similar virtualization platforms), including strong understanding of virtualization concepts, server deployments, and system ...

TEKsystems

Field Systems Engineer

Chicago, IL

$50 - $52.50/hr

Windows Server and Hypervisor experience (VMware, Hyper-V, or similar virtualization platforms), including strong understanding of virtualization concepts, server deployments, and system ...

Embark Recovery

Systems Administrator

Chicago, IL

$90K - $110K/yr

DUTIES Manage and maintain server environments including Windows Server, Linux, VMware ESXi, and cloud platforms such as AWS and Azure. Oversee system architecture design, configuration management ...

New

Bactech

System Administrator

Rolling Meadows, IL · On-site

Demonstrated Knowledge of HP/IBM/Dell server hardware, Service Management Tool, Microsoft Cluster Services, Windows scripting, Symantec AV, Sophos AV, and/or TSM or NetBackup enterprise backup ...

Bactech

System Administrator

Rolling Meadows, IL · On-site

... Windows Server Administration experience. • 6 years of Windows Operating System experience. • Demonstrated Knowledge of HP/IBM/Dell server hardware, Service Management Tool, Microsoft Cluster ...

Noventech, Inc.

Systems Analyst - Tier 2

Lombard, IL · On-site

$70K - $90K/yr

You will work with a variety of client environments, including Microsoft 365, Windows Server, networking equipment, firewalls, cloud services, and business applications. You will receive escalated ...

Noventech, Inc.

Systems Analyst - Tier 2

Lombard, IL · On-site

$70K - $90K/yr

You will work with a variety of client environments, including Microsoft 365, Windows Server, networking equipment, firewalls, cloud services, and business applications. You will receive escalated ...

Noventech, Inc.

Systems Analyst Tier 2

Lombard, IL · On-site

$70K - $90K/yr

You will work with a variety of client environments, including Microsoft 365, Windows Server, networking equipment, firewalls, cloud services, and business applications. You will receive escalated ...

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Showing results 21-40

All JobsWindows Server JobsWindows Server Jobs in Chicago, IL

Windows Server information

See Chicago, IL salary details

$92.2K

$111.1K

$128.3K

How much do windows server jobs pay per year?

As of Aug 19, 2026, the average yearly pay for windows server in Chicago, IL is $111,065.00, according to ZipRecruiter salary data. Most workers in this role earn between $101,500.00 and $120,500.00 per year, depending on experience, location, and employer.

What is a Windows Server?

A Windows Server job involves managing, maintaining, and troubleshooting Microsoft's Windows Server operating systems in an IT environment. Professionals in this role configure servers, ensure security, handle updates, and support network infrastructure. They may also work with Active Directory, virtualization, and cloud integration to optimize system performance.

What are the typical day-to-day responsibilities of a Windows Server administrator?

As a Windows Server Administrator, your daily tasks often include monitoring server performance, applying updates and patches, managing user accounts through Active Directory, and resolving system issues to minimize downtime. You may also be responsible for backup operations, security checks, and supporting end-users or other IT staff with server-related concerns. Collaboration is common, as you'll frequently work alongside network administrators, cybersecurity professionals, and support teams to ensure seamless IT operations. These responsibilities require a proactive approach to system management and strong attention to detail. Developing your skills in this role can open up opportunities for advancement into senior administration or network management positions.

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

To thrive as a Windows Server Administrator, you need a solid understanding of Windows Server operating systems, Active Directory, networking, and systems troubleshooting, often backed by a relevant degree or IT certifications. Familiarity with tools such as PowerShell, Hyper-V, and certifications like Microsoft Certified: Windows Server Fundamentals or MCSA are typically required. Strong problem-solving skills, effective communication, and the ability to work well under pressure are important soft skills for this role. These abilities are essential to ensure reliable system performance, rapid issue resolution, and successful collaboration within IT teams.

What are Windows Server roles?

Windows Server roles are specific functions or services that a Windows Server operating system can perform, such as Active Directory Domain Services, DHCP, DNS, File and Storage Services, and Web Server (IIS). These roles enable the server to provide various network and infrastructure services essential for enterprise environments and can be installed and managed through Server Manager or PowerShell. Understanding these roles helps IT professionals configure and optimize server environments effectively.

What can you do with a Windows Server?

A Windows Server administrator manages and maintains Windows Server environments, including configuring network services, managing user accounts, deploying applications, and ensuring security and system stability. They also handle tasks such as setting up Active Directory, virtualization with Hyper-V, and implementing backup and disaster recovery solutions.

What are the most commonly searched types of Windows Server jobs in Chicago, IL?

The most popular types of Windows Server jobs in Chicago, IL are:

What are popular job titles related to Windows Server jobs in Chicago, IL?

For Windows Server jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Windows Server jobs in Chicago, IL look for?

The top searched job categories for Windows Server jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Windows Server jobs?

Cities near Chicago, IL with the most Windows Server job openings:

Windows Server jobs near you
Infographic showing various Windows Server job openings in Chicago, IL as of August 2026, with employment types broken down into 75% Full Time, 20% Part Time, and 5% Contract. Highlights an 93% Physical, 3% Hybrid, and 4% Remote job distribution, with an average salary of $111,065 per year, or $53.4 per hour.

System Automation Engineer

Computer Futures

Chicago, IL

Contractor

Re-posted 22 days ago

Job description

Company Description

Computer Futures is a leading IT recruitment consultancy, specializing in placing IT experts in permanent and contract roles across Asia, Europe and the US. 

With a proven track record in IT recruitment, we enjoy success within all sectors and business types, placing a candidate every 38 minutes. From single job vacancies to large-scale projects, our proficiency in providing exceptional professionals across the board has carved our reputation as a secure and significant supplier partner. 

A robust and financially strong business we have grown organically from our first office in London in 1986, to 18 offices in Europe; including Amsterdam, Brussels, Dublin, Edinburgh, Frankfurt, Hamburg, Munich and Paris as well as one office in San Francisco and Tokyo. 

Gaining market share, year-on-year, we have the largest client base of any IT recruitment business across Europe. We work with a range of clients, from SMEs to large multi-nationals and high-profile names. 

Passionate about recruitment, our 350+ specialist IT recruitment consultants' priority is to secure the right person for the right role, within a specified time frame and budget. Through Computer Futures' methodology, our consultants - who focus on a specific IT technical market and geographical area - create a bespoke service to meet our individual clients' recruitment needs.

Job Description

Split time approximately 60:40 between project based work and support based work; split may change depending on workload

Strong Windows Server administration experience in an enterprise environment

Devise and automate procedures for provisioning new system instances

Implement and lead continuous integration, automated testing, configuration management, release management, deployment, cloud hosting and systems monitoring

Support incoming server incident and request tickets in a distributed high volume environment

Rack, configure, decommission, and deploy OS for physical servers in co-located and local datacenters

Administer and troubleshoot OS-level issues in a VM environment, as well as hardware problems on physical servers (Dell, Cisco)

Manage Print Server queues, drivers, and DR

Manage and respond to daily alerts from monitoring systems (SCOM, xMatters)

Patch deployments to 1,500+ Windows Servers during predetermined outage windows; software, driver, and firmware deployment and configuration

Qualifications

- 5+ years of relevant, hands-on experience supporting Windows Server 2012/2008 (R2) in an Enterprise Environment

 Expertise with scripting languages such as Powershell, VB Scripting, Python is desirable.

 Experience with server management tools such as MS System Center (preferred), Altiris, or similar

 Experience managing an automated patching of Windows Servers with SCCM (preferred), Lumension, or a similar tool

 Thorough understanding of working principles, and experience supporting Active Directory, Group Policy, Microsoft DNS, IIS, Virtualization (Hyper-V or VMware), Symantec Endpoint Protection (or similar enterprise AV)

 Experience with monitoring systems such as SCOM, WhatsUpGold, NetScout, HP NMS, Syslog, or others

 Bachelor's degree in Computer Science, Management Information Systems, or equivalent work experience

 Experience in Financial sector preferred

Additional Information

All your information will be kept confidential according to EEO guidelines.

Look for: Danielle

Phone: 346 231 7544

Email: d.garan@computerfutures. com

Apply