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Windows Installer Jobs in Chicago, IL (NOW HIRING)

Renuity

Bath Installer

Bensenville, IL · On-site

$21.50 - $26/hr

... City Windows & Baths, FHIA Remodeling, Statewide Remodeling, MaxHome, Rite Window, and Closet ... installation--at competitive prices. At Renuity, you'll join a dynamic, fast-paced, and ...

Renuity

Bath Installer

Chicago, IL · On-site

$21.50 - $26/hr

... City Windows & Baths, FHIA Remodeling, Statewide Remodeling, MaxHome, Rite Window, and Closet ... installation-at competitive prices. At Renuity, you'll join a dynamic, fast-paced, and ...

Westward360

Invest Handyman

Chicago, IL

$27 - $30/hr

Doors & Windows: installation and repairs * Carpentry: crown molding, chair rails, wainscoting, base molding, stairs, railings, shelving, trim. * Electrical : fixtures, ceiling fans, GFCIs, outlets ...

Westward360

Invest Handyman

Chicago, IL · On-site

$27 - $30/hr

Doors & Windows: installation and repairs * Carpentry: crown molding, chair rails, wainscoting, base molding, stairs, railings, shelving, trim. * Electrical : fixtures, ceiling fans, GFCIs, outlets ...

Westward360

Invest Handyman

Chicago, IL

$27 - $30/hr

Doors & Windows: installation and repairs * Carpentry: crown molding, chair rails, wainscoting, base molding, stairs, railings, shelving, trim. * Electrical : fixtures, ceiling fans, GFCIs, outlets ...

M&M

Window & Door Technician (Repair + Install)

Crete, IL · On-site

$33 - $34/hr

If you've worked with windows, doors, or exterior installs and want steady work without slow seasons, this is a strong opportunity.We're hiring a hands-on Window & Door Technician who can handle ...

M&M

Window & Door Technician (Repair + Install)

Crete, IL · On-site

$33 - $34/hr

If you've worked with windows, doors, or exterior installs and want steady work without slow seasons, this is a strong opportunity. We're hiring a hands-on Window & Door Technician who can handle ...

Westward360

Invest Handyman

Chicago, IL · On-site

$27 - $30/hr

Doors & Windows: installation and repairs * Carpentry: crown molding, chair rails, wainscoting, base molding, stairs, railings, shelving, trim. * Electrical : fixtures, ceiling fans, GFCIs, outlets ...

McCann Window & Exteriors

Remodeler

Northbrook, IL · On-site

$60K - $90K/yr

We are hiring Window and Door Installers Now! Good pay. Lots of work. Do you want to be recognized ... windows, doors, and/or siding. * Ready and equipped to work. * Strong work ethic. * Provide ...

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Showing results 21-40

All JobsWindows Installer JobsWindows Installer Jobs in Chicago, IL

Windows Installer information

See Chicago, IL salary details

$13

$34

$129

How much do windows installer jobs pay per hour?

As of Aug 12, 2026, the average hourly pay for windows installer in Chicago, IL is $34.90, according to ZipRecruiter salary data. Most workers in this role earn between $19.81 and $29.71 per hour, depending on experience, location, and employer.

What are some common challenges Windows installers face when setting up operating systems in varied environments?

Windows Installers often encounter challenges such as hardware compatibility issues, managing driver installations, and ensuring seamless integration with existing network infrastructure. Each environment may have unique requirements, such as custom configurations or legacy software, which can add complexity to the installation process. Additionally, coordinating with IT teams or end-users to minimize downtime and performing thorough post-installation testing are crucial parts of the role. Successfully navigating these challenges requires strong troubleshooting skills and effective communication.

What is a Windows installer?

Windows Installers are professionals who install, configure, and maintain the Microsoft Windows operating system and related software on computers and servers. Their responsibilities include setting up new hardware, upgrading or repairing existing systems, and ensuring that Windows runs smoothly and securely. They may also troubleshoot issues, install updates, and help users with software compatibility. Windows Installers often work in IT departments, helping businesses and individuals keep their systems up to date and secure.

How much do you get paid to install Windows Installer?

The role of a Windows Installer typically involves deploying and configuring Windows operating systems and software, with salaries ranging from $40,000 to $80,000 annually depending on experience, location, and certifications. Entry-level positions may start lower, while experienced technicians or specialists can earn higher wages, especially in enterprise environments.

What is the difference between Windows Installer vs Software Deployment Specialist?

AspectWindows InstallerSoftware Deployment Specialist
Primary RoleCreates, manages, and troubleshoots Windows installation packagesImplements and manages software deployment across networks
Required SkillsKnowledge of MSI, scripting, and Windows OSDeployment tools, scripting, network management
Work EnvironmentIT support, software development, system administrationIT teams, system administrators, network operations
CertificationsMicrosoft Certified: Windows Client or ServerITIL, Microsoft Deployment certifications

While Windows Installer focuses on creating and troubleshooting Windows installation packages, a Software Deployment Specialist manages the broader process of deploying software across multiple systems. Both roles require knowledge of Windows environments and scripting, but the Installer is more technical in package creation, whereas the Specialist handles deployment strategies and tools.

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

To thrive as a Windows Installer, you need a solid understanding of operating systems, system configuration, and troubleshooting, usually supported by experience or certifications such as CompTIA A+ or Microsoft Certified: Modern Desktop Administrator Associate. Familiarity with deployment tools like Windows Deployment Services (WDS), System Center Configuration Manager (SCCM), and imaging software is commonly required. Attention to detail, problem-solving abilities, and effective communication are crucial soft skills in this role. These skills ensure efficient and reliable system installations, minimize downtime, and provide users with seamless IT experiences.
What are popular job titles related to Windows Installer jobs in Chicago, IL? For Windows Installer jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Windows Installer jobs in Chicago, IL look for? The top searched job categories for Windows Installer jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Windows Installer jobs? Cities near Chicago, IL with the most Windows Installer job openings:
Windows Installer jobs near you
Infographic showing various Windows Installer job openings in Chicago, IL as of August 2026, with employment types broken down into 78% Full Time, 14% Part Time, and 8% Contract. Highlights an 92% Physical, 2% Hybrid, and 6% Remote job distribution, with an average salary of $72,582 per year, or $34.9 per hour.

Senior Microsoft Windows Field Deployment Technician

MKS2 Technologies

Chicago, IL

$60K - $70K/yr

Full-time

Re-posted 4 days ago

Job description

MKS2 Technologies, LLC, an award-winning high growth small business, creates innovative and customer-centric technology solutions in the areas of Cyber Security, Instructional Design and Training, Software Engineering and IT Support Services to improve the security and well-being of our clients. Our commitment to excellence and our "Mission First" orientation has resulted in steady growth and an expanding client base across government agencies. We have employees nationwide and for the past three consecutive years were named one of the fastest growing Veteran-owned companies in the nation. Please take a moment to browse through our website and learn more about what it means to serve with MKS2.

Position Title: Senior Microsoft Windows Field Deployment Technician
As a Senior Microsoft Windows Field Deployment Technician on our project, you'll work with a team of onsite technicians supporting the VA's EHR deployment and training project and assist with oversight of workload. In this role you will be deploying, imaging, and setting up equipment (PCs, Laptops, Docking Stations, Monitors, Printers, Scanners, and Network Connections) around the VA medical center campus as well as offsite training centers. This role combines strong technical skills with an emphasis on delivering a high level of customer service. You will be responsible for unboxing, setting up, installing, configuring, removing equipment, re-packaging hardware for shipment, and with limited supervision. This role will also require setup of equipment at various training sites, verifying each computer has the most current VA computer image, computer is available for scheduled security scans and update, Active Directory assignment for training use, configure network connectivity in the training room, and computer peripherals are installed at each training seat. You will be managing inventory and network connectivity at each training site and ensuring connectivity during all training sessions. This position is located onsite at Veterans' Administration Medical Centers and offsite training locations with daytime hours and may require evening hours and the potential for weekend hours. The staff may be required to travel to other sites outside of the metropolitan area throughout the week.
You Have:
  • 5 years' experience in imaging, installing computer equipment and managing teams of technical staff
  • Must be able to unpack/re-pack, move, and install pallets of IT equipment with each item weighing up to 50 pounds with no restrictions
  • Must have personal transportation available during work hours
  • Will need to consistently traverse around the site campus transporting equipment to various office buildings and frequently stoop, crouch, and reach to setup/remove computers/pull cords under desks and in server closets
  • Will frequently need to be able to push carts carrying equipment
  • Experience with hardware and software support, troubleshooting, system imaging, hardware break-fix support (i.e. laptops, desktops, and printers), refresh, upgrade, and deployment projects as well as excellent customer service skills
  • Experience with conducting routine system administration tasks and logging data in system admin logs
  • Experience with maintaining troubleshooting a wide variety of systems and networks, including high availability systems
  • Knowledge of debugging protocols and processes and the ability to work independently while providing excellent customer service
  • Bachelor's degree in computer science, Information System, Information Technology, or Equivalent and 5 total years of experience; or 13 total years of experience in lieu of a degree
Nice If You Have:
  • Experience with the ServiceNow ticketing system a plus
  • Experience with the VA
  • Public Trust clearance
  • Experience with Microsoft Windows desktop deployments
  • Experience as IT helpdesk Tier 1 or 2
LCAT: Senior Test Engineer
Salary Range: $60,000-$70,000

Diversity creates a healthier atmosphere: MKS2 Technologies is proud to be an Equal Employment Opportunity / Affirmative Action employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, protected veteran status, disability status, sexual orientation, gender identity or expression, marital status, genetic information, or any other characteristic protected by law.