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Windows Engineer Jobs in Chicago, IL (NOW HIRING)

TEKsystems c/o Allegis Group

Intune Engineer

Lake Forest, IL · On-site

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Familiar with Windows Update for Business and update rings, feature and quality update deployments ... Use AI-assisted engineering tools - Claude Code, Cowork, GitHub Copilot, Microsoft Copilot, and ...

TEKsystems

Intune Engineer

Lake Forest, IL

$65 - $70/hr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

This role owns hands-on engineering and operations across Microsoft Intune and Microsoft ... Windows endpoints and a multi-platform Intune estate spanning Windows, macOS, iOS/iPadOS, and ...

TEKsystems

Intune Engineer

North Chicago, IL

$65 - $70/hr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

This role owns hands-on engineering and operations across Microsoft Intune and Microsoft ... Windows endpoints and a multi-platform Intune estate spanning Windows, macOS, iOS/iPadOS, and ...

TEKsystems c/o Allegis Group

Intune Engineer

North Chicago, IL · On-site

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Familiar with Windows Update for Business and update rings, feature and quality update deployments ... Use AI-assisted engineering tools - Claude Code, Cowork, GitHub Copilot, Microsoft Copilot, and ...

Sterling Engineering Inc.

Systems Engineer

Willowbrook, IL · On-site

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

This is a hands-on technical position focused on Windows and Linux server administration ... engineering. * Strong experience with Windows and Linux server administration. * 4-6 years of ...

TEKsystems

Field 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 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 ...

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Showing results 21-40

All JobsWindows Engineer JobsWindows Engineer Jobs in Chicago, IL

Windows Engineer information

See Chicago, IL salary details

$10

$57

$69

How much do windows engineer jobs pay per hour?

As of Aug 17, 2026, the average hourly pay for windows engineer in Chicago, IL is $57.60, according to ZipRecruiter salary data. Most workers in this role earn between $49.57 and $63.46 per hour, depending on experience, location, and employer.

How much do Windows engineers make?

Windows engineers typically earn a median annual salary ranging from $70,000 to $110,000, depending on experience, location, and certifications such as Microsoft Certified: Windows Server. Senior roles or those with specialized skills in scripting, virtualization, or cloud integration can earn higher salaries.

What does a Windows engineer do?

A Windows Engineer is responsible for designing, implementing, and maintaining Microsoft Windows-based systems within an organization. Their duties include installing and configuring Windows servers and workstations, managing system updates and security patches, troubleshooting technical issues, and ensuring network performance and security. They often work with other IT professionals to support business operations and may also be involved in virtualization, cloud services, and scripting automation tasks. A Windows Engineer ensures that the organization's Windows infrastructure is reliable, secure, and optimized for business needs.

How does a Windows engineer typically collaborate with other IT teams within an organization?

Windows Engineers regularly work alongside network administrators, security analysts, and application support teams to ensure seamless integration and optimal performance of Windows-based systems. Collaboration often involves troubleshooting complex issues, coordinating system updates or deployments, and aligning security protocols across departments. Effective communication skills and the ability to translate technical concepts for non-technical stakeholders are essential for success in this collaborative environment.

What are the key skills and qualifications needed to thrive as a Windows engineer, and why are they important?

To thrive as a Windows Engineer, you need a strong background in Windows operating systems, system administration, and networking, often supported by a degree in computer science or a related field. Familiarity with tools such as Active Directory, PowerShell scripting, and certifications like Microsoft Certified: Windows Server or Azure Administrator are typically required. Excellent problem-solving skills, attention to detail, and effective communication help you collaborate with teams and handle complex technical issues. These skills and qualifications ensure reliable system performance, security, and efficient support in enterprise IT environments.

What is the difference between Windows Engineer vs Network Administrator?

AspectWindows EngineerNetwork Administrator
CertificationsMicrosoft Certified: Windows Server, CompTIA Network+Cisco CCNA, CompTIA Network+
Work EnvironmentFocus on Windows OS, servers, and related infrastructureManage entire network, including routers, switches, and security
Employer UsageIT departments supporting Windows-based systemsOrganizations needing network infrastructure management
Search IntentRoles related to Windows server managementRoles related to network infrastructure and security

While both roles work within IT infrastructure, a Windows Engineer specializes in Windows server environments, whereas a Network Administrator manages overall network systems and connectivity. Understanding these differences helps in choosing the right career path or job focus.

Windows Engineer jobs near you
Infographic showing various Windows Engineer job openings in Chicago, IL as of August 2026, with employment types broken down into 89% Full Time, 5% Part Time, and 6% Contract. Highlights an 87% Physical, 5% Hybrid, and 8% Remote job distribution, with an average salary of $119,798 per year, or $57.6 per hour.

Senior Software Engineer, Windows/Desktop Applications - Chicago, IL, USA

Speechify

Chicago, IL

$133K - $166K/yr

Full-time

Re-posted 18 days ago

Job description

Mission

The mission of Speechify is to make sure that reading is never a barrier to learning.

Over 50 million people use Speechify's text-to-speech products to turn whatever they're reading - PDFs, books, Google Docs, news articles, websites - into audio, so they can read faster, read more, and remember more. Speechify's text-to-speech reading products include its iOS app, Android App, Mac App, Chrome Extension, and Web App. Google recently named Speechify the Chrome Extension of the Year and Apple named Speechify its 2025 Design Award winner for Inclusivity.  

Today, nearly 200 people around the globe work on Speechify in a 100% distributed setting - Speechify has no office. These include frontend and backend engineers, AI research scientists, and others from Amazon, Microsoft, and Google, leading PhD programs like Stanford, high growth startups like Stripe, Vercel, Bolt, and many founders of their own companies

What You'll Do
  • Lead the design, architecture, and development of native Windows desktop applications using Windows App SDK, WinUI (or related UI frameworks), C#, XAML, and - when needed - C++.
  • Define and enforce best-practices for Windows desktop development across the codebase: code architecture, performance, memory usage, responsive UI, cross-version compatibility (Windows 10/11+), and maintainability.
  • Drive accessibility efforts: integrate and validate support for accessibility APIs (e.g. Microsoft UI Automation or other relevant Windows accessibility frameworks), ensure UI controls, focus management, keyboard navigation, screen-reader support, and usability for users with disabilities.
  • Collaborate closely with product designers, UX researchers, QA, and other stakeholders to shape feature planning, UI/UX architecture, and long-term roadmap for the Windows platform.
  • Take ownership of full lifecycle of features: conception design implementation testing release maintenance. Ensure quality, reliability, and consistency across releases.
  • Identify, diagnose, and resolve complex bugs, performance bottlenecks, memory leaks, rendering issues, or compatibility problems - and propose robust architectural or design solutions.
 
An ideal candidate should have

Required:

  • 3+ in Windows desktop application development using Windows App SDK, WinUI (or similar), C#, XAML - and ideally additional experience with native Windows code (C++, Win32/WinRT/COM).
  • Deep understanding of Windows application architecture, including interop between managed code (.NET) and native code.
  • Proven track record of designing, building, and shipping production-quality desktop applications, with an emphasis on reliability, performance, scalability, and maintainability.
  • Strong experience with accessibility APIs on Windows (e.g. Microsoft UI Automation or similar), and a dedication to building accessible and inclusive software.
  • Excellent software engineering fundamentals: OOP, design patterns, data structures, algorithms, memory management, multi-threading or asynchronous programming (where relevant).
  • Experience leading technical design, mentoring other engineers, conducting code reviews, and making architecture-level decisions.
  • Strong communication skills; ability to articulate tradeoffs, collaborate with cross-functional teams, and drive consensus.
  • A user-centric mindset: focus on building polished, intuitive, and accessible experiences for end users.

Preferred / Bonus:

  • Experience with writing automated tests for UI - unit tests, integration tests, UI automation tests; familiarity with relevant testing frameworks.
  • Experience with performance optimization for desktop apps (memory usage, startup time, rendering performance, high-DPI support, responsiveness under load).
  • Experience with localization/globalization, right-to-left UI support, internationalization, accessibility for multiple regions.
  • Familiarity with telemetry, analytics, crash reporting, logging, and error monitoring in desktop applications.
  • Previous experience in shaping CI/CD workflows, release pipelines, and deployment strategies for desktop applications.
  • Demonstrated ability to take ownership of feature areas or modules and drive them long-term, including maintenance, refactoring, and technical debt management.

What we offer

  • A high-impact role: you will define architecture, shape the future of our Windows product, and directly influence what millions of users see and experience.
  • A collaborative, flat-structure engineering culture - you are not just a coder, but a builder and a decision-maker.
  • Opportunities to lead - mentor others, steer technical direction, and grow into broader technical leadership (e.g. Tech Lead, Architect).
  • Flexibility, autonomy, and responsibility: you define how to solve problems, own features end-to-end, and contribute to long-term product vision.
  • A purpose-driven mission: building software that's reliable, accessible, and user-centered - making a real difference for people.

The United States Based Salary range for this role is: 140,000-200,000 USD/Year + Bonus + Stock depending on experience             

Think you're a good fit for this job? 

Tell us more about yourself and why you're interested in the role when you apply.
And don't forget to include links to your portfolio and LinkedIn.

Not looking but know someone who would make a great fit? 
Refer them! 

Speechify is committed to a diverse and inclusive workplace. 
Speechify does not discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status.

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