1

Senior Windows Systems Engineer Jobs in Chicago, IL

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.

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 ...

Senior Systems Engineer

Chicago, IL · On-site

$107K - $147K/yr

Senior Systems Engineer, Chicago IL This Senior Systems Engineer position is fully onsite. Responsibilities: - Work collaboratively with technology and business teams on all aspects of a global ...

Senior Systems Engineer

Chicago, IL

$107K - $147K/yr

Job Summary Senior Systems Engineer is responsible for resolving escalated service incidents and ... maintaining Windows Server 2008 or later systems 5-7 years of experience engineering and ...

Systems Engineer - Hybrid

Oak Forest, IL · On-site

$100K - $115K/yr

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 ...

Senior Trading Systems Engineer

Chicago, IL · On-site

$107K - $147K/yr

Senior Trading Systems Engineer, Chicago, IL This Senior Trading Systems Engineer position is 100% fully onsite. Responsibilities: - Work collaboratively with technology and business teams on all ...

next page

Showing results 1-20

Senior Windows Systems Engineer information

See Chicago, IL salary details

$36

$65

$82

How much do senior windows systems engineer jobs pay per hour?

As of Aug 11, 2026, the average hourly pay for senior windows systems engineer in Chicago, IL is $65.41, according to ZipRecruiter salary data. Most workers in this role earn between $57.50 and $78.08 per hour, depending on experience, location, and employer.

What are some common challenges faced by senior Windows systems engineers when managing large-scale enterprise environments?

Senior Windows Systems Engineers often encounter challenges such as ensuring system uptime during maintenance, managing complex Active Directory environments, and troubleshooting issues across multiple Windows servers. Balancing security requirements with user accessibility, keeping up with frequent updates and patches, and coordinating with other IT teams for seamless integration can also be demanding. Effective communication and strong problem-solving skills are key to overcoming these challenges and maintaining a stable, secure infrastructure.

What is the difference between Senior Windows Systems Engineer vs Windows Systems Administrator?

AspectSenior Windows Systems EngineerWindows Systems Administrator
CertificationsMCSE, MCSA, VMwareMCSE, MCSA
Work EnvironmentDesign, implementation, troubleshooting complex systemsDay-to-day maintenance, user support, system monitoring
ResponsibilitiesArchitecting solutions, optimizing performance, leading projectsManaging user accounts, backups, system updates

The Senior Windows Systems Engineer typically focuses on designing and implementing complex Windows infrastructure, while the Windows Systems Administrator handles routine maintenance and support tasks. Both roles require similar certifications and work in Windows-based environments, but the engineer role involves higher-level planning and problem-solving.

What are the key skills and qualifications needed to thrive as a senior Windows systems engineer?

To thrive as a Senior Windows Systems Engineer, you need expert knowledge of Windows Server environments, Active Directory, and strong troubleshooting skills, typically backed by a bachelor’s degree in IT or related field. Familiarity with tools like PowerShell, virtualization platforms (VMware/Hyper-V), and certifications such as Microsoft Certified: Windows Server Hybrid Administrator Associate are highly valued. Strong problem-solving abilities, effective communication, and the capacity to work independently or lead teams distinguish top performers in this role. These skills ensure reliable system performance, secure infrastructure, and seamless operations within complex enterprise environments.

How much money does a senior Windows Systems Engineer make?

A senior Windows Systems Engineer typically earns between $90,000 and $130,000 annually, depending on experience, location, and certifications such as Microsoft Certified Solutions Expert (MCSE). They often work with enterprise environments, managing Windows servers, Active Directory, and virtualization tools like Hyper-V or VMware.

What does a senior Windows systems engineer do?

A Senior Windows Systems Engineer is responsible for designing, implementing, and maintaining complex Windows-based server environments for organizations. They manage system configurations, troubleshoot technical issues, and ensure the security and performance of Windows servers. Additionally, they often lead projects, mentor junior engineers, and collaborate with other IT teams to support business operations. Their role is critical in ensuring that the organization's IT infrastructure runs efficiently and securely.
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 cities near Chicago, IL are hiring for Senior Windows Systems Engineer jobs? Cities near Chicago, IL with the most Senior Windows Systems Engineer job openings:
Infographic showing various Senior Windows Systems Engineer job openings in Chicago, IL as of August 2026, with employment types broken down into 95% Full Time, and 5% Contract. Highlights an 68% In-person, 16% Hybrid, and 16% Remote job distribution, with an average salary of $136,043 per year, or $65.4 per hour.

Senior Windows Systems Engineer

TEKsystems

Chicago, IL • Hybrid

$65 - $70/hr

Contractor

Medical, Dental, Vision, Life, Retirement, PTO

Posted 20 days ago


Job description

Job Description:

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. This resource must have experience in an enterprise multi-domain environment. They must have very strong PowerShell scripting skills and the ability to write their own scripts.

This environment is high regulated so documentation is very important. Communication is also key in this environment, so strong skills in communication are also required. This person must also be able to perform root cause analysis.

Location: This role can sit out of Chicago, Philadelphia, Baltimore, or Kennett Square. This resource must be onsite 3 days a week.

Job Type & Location

This is a Contract position based out of Chicago, IL.

Pay and Benefits

The pay range for this position is $65.00 - $70.00/hr.

Eligibility requirements apply to some benefits and may depend on your job classification and length of employment. Benefits are subject to change and may be subject to specific elections, plan, or program terms. If eligible, the benefits available for this temporary role may include the following: • Medical, dental & vision • Critical Illness, Accident, and Hospital • 401(k) Retirement Plan – Pre-tax and Roth post-tax contributions available • Life Insurance (Voluntary Life & AD&D for the employee and dependents) • Short and long-term disability • Health Spending Account (HSA) • Transportation benefits • Employee Assistance Program • Time Off/Leave (PTO, Vacation or Sick Leave)

Workplace Type

This is a hybrid position in Chicago,IL.

Application Deadline

This position is anticipated to close on Jul 31, 2026.

About TEKsystems

We're partners in transformation. We help clients activate ideas and solutions to take advantage of a new world of opportunity. We are a team of 80,000 strong, working with over 6,000 clients, including 80% of the Fortune 500, across North America, Europe and Asia. As an industry leader in Full-Stack Technology Services, Talent Services, and real-world application, we work with progressive leaders to drive change. That's the power of true partnership. TEKsystems is an Allegis Group company.

The company is an equal opportunity employer and will consider all applications without regards to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

About TEKsystems and TEKsystems Global Services

We’re a leading provider of business and technology services. We accelerate business transformation for our customers. Our expertise in strategy, design, execution and operations unlocks business value through a range of solutions. We’re a team of 80,000 strong, working with over 6,000 customers, including 80% of the Fortune 500 across North America, Europe and Asia, who partner with us for our scale, full-stack capabilities and speed. We’re strategic thinkers, hands-on collaborators, helping customers capitalize on change and master the momentum of technology. We’re building tomorrow by delivering business outcomes and making positive impacts in our global communities. TEKsystems and TEKsystems Global Services are Allegis Group companies. Learn more at TEKsystems.com.

The company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

San Francisco Fair Chance Ordinance: Pursuant to the San Francisco Fair Chance Ordinance, for all positions located in the city and county of San Francisco, we will consider for employment qualified applicants with arrest and conviction records.

Massachusetts Lie Detector: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Use of Artificial Intelligence (AI): We may use Artificial Intelligence (AI) to support parts of our hiring process, including sourcing, screening, and evaluating candidates. AI helps assess applications and qualifications, but final decisions are made by our hiring team. By applying, you acknowledge and agree that your application may be reviewed using AI tools.