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Windows Systems Engineer Jobs in Chicago, IL (NOW HIRING)

TEKsystems

Senior Windows Systems Engineer

Chicago, IL · Hybrid

$65 - $70/hr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Our client is looking for a tenured Windows Engineer. This role is supporting a multi year project to add multiple domains. This role is very heavy in Active Directory so that experience is critical.

Data Bridge Consultants

Windows System Engineer.

Chicago, IL · On-site

  • Medical

  • Dental

  • Life

  • Retirement

Employment Type: Full-Time Execute enterprise-wide Windows infrastructure engineering tasks and ... Manage and monitor all installed systems and infrastructure. * Install, configure, test and ...

Sterling Engineering Inc.

Systems Engineer

Willowbrook, IL · On-site

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

Systems Engineer Location: Willowbrook, Illinois Hire Type: Full-Time Shift: On-Site Compensation ... This is a hands-on technical position focused on Windows and Linux server administration ...

Infobahn SoftWorld Inc

Systems Engineer

Elgin, IL · On-site

Windows and Google programs preferable Required Experience Level: Entry Level Work Environment: Office and programming on a showroom floor Key Contributions (First 90-120 Days): Learning system ...

Judge Group, Inc.

Systems Engineer - Hybrid

Oak Forest, IL · On-site

$100K - $115K/yr

  • PTO

A Tech company is looking for a Sr Systems Engineer with 5+ years of experience. In this role you ... The right candidate will have experience working in a Windows environment and be comfortable with ...

TEKsystems

Field Systems Engineer

Chicago, IL

$50 - $52.50/hr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Windows Server and Hypervisor experience (VMware, Hyper-V, or similar virtualization platforms ... The field engineer acts as a generalist across servers, virtualization, operating systems ...

TEKsystems c/o Allegis Group

Field Systems Engineer

Chicago, IL · On-site

$50 - $52.50/hr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Windows Server and Hypervisor experience (VMware, Hyper-V, or similar virtualization platforms ... The field engineer acts as a generalist across servers, virtualization, operating systems ...

Robert Half

Systems Engineer

Libertyville, IL · On-site

$50 - $60/hr

We are looking for a Systems Engineer to support and evolve a complex enterprise infrastructure ... Administer physical and virtual server environments, including Windows Server platforms, VMware and ...

TEKsystems

Systems Engineer - Traveling

Chicago, IL

$50 - $60/hr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

The ideal candidate will have hands-on experience with Windows Server, VMware/Hyper-V ... We're looking for hands-on Systems Engineers or Administrators with experience in Windows Server ...

Prinova Group LLC

Network Systems Engineer

Itasca, IL · On-site

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Maintain and administer Windows Server, virtualized environments (VMware/Hyper-V), and cloud-based ... network/systems engineering roles. * Experience with enterprise networking technologies.

Motorola

Sr. Systems Engineer

Schaumburg, IL · On-site

$90K - $100K/yr

  • Medical

  • Dental

  • Retirement

We are seeking a Sr. Systems Engineer to serve as a high-level technical escalation point for our ... Operating Systems expertise in installing, configuring, and troubleshooting Windows Server 2008 ...

SG Cap Trading

Linux Systems Engineer

Chicago, IL

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

Linux Systems Engineer ID: 1018 Location: Chicago, IL More about this job > Description SG is a ... Set up desktops, laptops, and virtual machines (Linux, Windows, Mac). Support SQL database ...

TEKsystems c/o Allegis Group

Field Systems Engineer

Chicago, IL · On-site

$50 - $52.50/hr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Windows Server, Virtualization / Hypervisors, SQL Server, Active Directory, Networking fundamentals ... activities, Field engineering or systems deployment backgrounds Job Type & Location This is a ...

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Windows Systems Engineer information

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How much do windows systems engineer jobs pay per hour?

As of Aug 17, 2026, the average hourly pay for windows systems engineer in Chicago, IL is $52.89, according to ZipRecruiter salary data. Most workers in this role earn between $41.83 and $63.41 per hour, depending on experience, location, and employer.

What is a Windows systems engineer?

A Windows Systems Engineer is responsible for designing, implementing, managing, and maintaining Windows-based infrastructure in an organization. They ensure system stability, security, and performance by configuring servers, managing updates, and troubleshooting issues. Their role often includes automation, scripting, and working with Active Directory, Group Policy, and virtualization technologies. Additionally, they collaborate with IT teams to optimize system efficiency and provide technical support.

What does a Windows systems engineer do?

Windows Systems Engineers are responsible for managing, monitoring, and maintaining Windows server environments, including performing routine updates, applying security patches, and troubleshooting system issues. Their day often involves configuring user access, managing Active Directory objects, scripting automation tasks, and responding to technical support requests. They also collaborate closely with network engineers, security specialists, and helpdesk teams to ensure system reliability and resolve incidents efficiently. This mix of proactive and reactive work provides variety and the opportunity to build both technical depth and teamwork skills.

What skills and qualifications are needed to be a Windows systems engineer?

A Windows Systems Engineer should have deep knowledge of Windows Server environments, networking principles, and scripting or automation, usually supported by a relevant degree and experience in IT infrastructure roles. Familiarity with tools such as Active Directory, PowerShell, virtualization platforms, and certifications like Microsoft Certified: Windows Server or Azure Administrator is highly valued. Strong troubleshooting, analytical thinking, and communication skills are essential for collaborating with technical teams and supporting end-users. These capabilities ensure stable, secure, and efficient IT systems, critical to business operations.

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

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

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

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

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

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

Windows Systems Engineer jobs near you
Infographic showing various Windows Systems Engineer job openings in Chicago, IL as of August 2026, with employment types broken down into 72% Full Time, and 28% Contract. Highlights an 67% In-person, and 33% Hybrid job distribution, with an average salary of $110,011 per year, or $52.9 per hour.

Systems Engineer - Windows

Hudson River Trading

Chicago, IL • On-site, Remote

Full-time

Re-posted 24 days ago

Job description

Hudson River Trading (HRT) is seeking a Windows Systems Engineer to join our Enterprise Engineering team. In this role, you will help scale HRT's global hybrid Windows deployment and develop automation, configuration-as-code, and infrastructure-as-code solutions to seamlessly manage fleets of top-of-the-line user endpoints, mission critical servers, cloud infrastructure, and secure remote computing environments around the world. You will apply configuration-as-code practices to reduce operational overhead, build PowerShell-based systems that improve platform stability and resilience, and enhance the reliability of our Windows platform by designing and implementing automation that identifies and resolves technical inefficiencies across on-premises and Azure infrastructure.

The ideal candidate is a Microsoft-based technology engineer and eager problem solver who is comfortable working in a fast-paced environment. Terrific communication and collaboration skills, as well as a positive attitude towards team members and internal customers, are crucial to success within this role. 

Responsibilities

  • Leverage configuration-as-code paradigms to reduce the operational overhead of managing Windows infrastructure
  • Use infrastructure-as-code to consistently configure Microsoft Azure resources
  • Develop PowerShell-based systems to automate operational tasks and enhance the reliability of the Windows platform
  • Leverage automation to identify and remediate technical inefficiencies across Windows endpoints, Windows infrastructure, and Microsoft Azure resources
  • Participate in ongoing engineering, maintenance, and support efforts to improve the Windows environment

Qualifications

  • 10+ years of experience as a Microsoft-based technology engineer
  • Experience using Ansible (or similar configuration-as-code tool) to manage a fleet of Windows devices
  • Proven ability to provision Microsoft Azure resources with Terraform
  • Proficiency with Microsoft Graph API development
  • Experience developing scripts and tools using PowerShell
  • Familiarity with Microsoft Intune, Autopilot, Entra ID, and Active Directory
  • A general design approach that incorporates security best practices, business continuity, high availability, and scalability
  • A self-motivated and driven work ethic

The estimated base salary range for this position is 150,000 to 250,000 USD per year (or local equivalent). The base pay offered may vary depending on multiple individualized factors, including location, job-related knowledge, skills, and experience. This role will also be eligible for discretionary performance-based bonuses and a competitive benefits package.

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