Top 86 Windows Systems Engineer Jobs in Chicago, IL

IT Technician Tier 3 – Senior Systems & Network Engineer
AMERICAN FREEDOM INSURANCE —Mount Prospect, IL
- $80,000 - $100,000 a year
- Weekends as needed
- Computer science
- Azure
- Computer Science
- Paid training
- Health savings account
Quick Apply
12d
Lead Associate Principal, Infrastructure Innovation & Automation
Options Clearing Corporation —Chicago, IL
- $136,500 - $189,800 a year
- Full-time
- Hybrid work
- Computer science
- Computer Science
- Windows
- Health insurance
- Dental insurance
Senior Windows Administator / Platform Engineer IV
Hudson Manpower —Illinois
- Full-time
- Remote
- Computer science
- Azure
- Computer Science
- Profit sharing
- Paid training
Quick Apply
Senior Windows Administator / Platform Engineer IV
Hudson Manpower —Skokie, IL
- Full-time
- Remote
- Computer science
- Azure
- Computer Science
- Profit sharing
- Paid training
Quick Apply
Staff Performance Engineer, ServiceNow Platform
ServiceNow —Chicago, IL
- $149,800 - $262,200 a year
- Online Application
- Hybrid work
- Windows
- Residential
- Java
- Employee stock purchase plan
- Health insurance
Quick Apply
10d
Infrastructure Engineer
Invenergy —Chicago, IL
- $137,000 - $160,000 a year
- Full-time
- System design
- 3 years
- Bachelor's degree
- Health insurance
- Dental insurance
Junior Network Engineer
Advyzon —Chicago, IL
- System design
- HIPAA
- Windows
- Health insurance
- Dental insurance
Desktop Support Engineer
Martin Brower —Rosemont, IL
- $87,000 - $109,000 a year
- Full-time
- Mid-level
- Windows
- High school diploma or GED
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Senior Endpoint Systems Engineer (HYBRID: Chicago)
Tempus —Chicago, IL
- $130,000 - $145,000 a year
- Full-time
- 5 years
- System design
- Windows
- Health insurance
9d
Infrastructure Engineer - Digital Network
Costco Wholesale —Addison, IL
- $85,000 - $225,000 a year
- On call
- Azure
- 5 years
- Windows
- AD&D insurance
- Employee stock purchase plan
Applications Engineer
Katten Muchin Rosenman LLP —Chicago, IL
- $100,000 - $125,000 a year
- Full-time
- Hybrid work
- Computer Science
- Mid-level
- Windows
- Disability insurance
- Health insurance
IT Engineer
XR Extreme Reach —Chicago, IL
- $80,000 - $90,000 a year
- Full-time
- Hybrid work
- Mid-level
- Continuous improvement
- SharePoint
Quick Apply
Storage Engineer
Ascendion —Chicago, IL
- $100,000 - $130,000 a year
- 5 years
- Mid-level
- Office
- Disability insurance
- Health insurance
Sr Systems Engineer- Reliability Engineering and Operations
CME Group —Chicago, IL
- $108,700 - $181,100 a year
- Full-time
- Windows
- Scripting
- Senior level
- Health insurance
- 401(k)
Senior Engineer
Midwest Vision Partners —Chicago, IL
- $105,000 - $118,000 a year
- Full-time
- Hybrid work
- Google Workspace
- Office
- Windows
- Paid parental leave
- AD&D insurance
Quick Apply
IT Site Reliability & Performance Engineer
AAR Corp. —Wood Dale, IL
- $110,000 - $130,000 a year
- Full-time
- Computer science
- Azure
- Computer Science
- AD&D insurance
- Paid holidays
Cloud Engineer (Remote)
Inspira Financial Trust, LLC —Oak Brook, IL
- $92,000 - $114,000 a year
- Remote
- Computer science
- Computer Science
- Research
- Health savings account
- Paid holidays
Enterprise Engineer III
Intone Networks —Chicago, IL
- Contract
- 5 years
- Windows
- Senior level
ASC IT Systems Engineer
Illinois Bone and Joint Institute LLC —Park Ridge, IL
- $90,000 - $660,000 a year
- Weekends as needed
- Google Workspace
- Computer science
- Computer Science
- Profit sharing
- Wellness program
Quick Apply
Senior Infrastructure Engineer
CIBC —Chicago, IL
- $140,000 - $150,000 a year
- Full-time
- Azure
- DevOps
- Windows
- Health savings account
- Health insurance
10d

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Windows Systems Engineer jobs near Chicago, IL

IT Technician Tier 3 – Senior Systems & Network Engineer

AMERICAN FREEDOM INSURANCE -
Mount Prospect, IL

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Job Details

$80,000 - $100,000 a year
12 days ago

Benefits

Paid training
Health savings account
Paid holidays
Dental insurance
401(k)
Paid time off
Vision insurance
401(k) matching
Opportunities for advancement

Qualifications

Endpoint Security
Azure
IT user and group management
GPO
Vendor coordination
Operating system updates
Public Cloud
VLAN
DHCP
Patch management
Computer management
Mentoring
DNS
Server virtualization
Networking equipment (troubleshooting support)
UEM
Windows support
Application Maintenance
Cloud solution engineering
Network monitoring tools
Desktop administration
Intune
System performance monitoring
VPN

Full Job Description

Description:

As an onsite Tier 3 Senior Systems & Network Engineer, you will serve as the highest level of technical escalation within the IT department. This role carries a dual mandate: maintaining the reliability, performance, and security of existing infrastructure, and engineering new solutions that support business growth and modernization.

You will handle complex technical issues that cannot be resolved by Tier 1 or Tier 2 support while simultaneously architecting and deploying next-generation infrastructure. Networking is a core competency for this role — you will own and evolve the organization’s network environment alongside Windows Server, Microsoft Azure, Intune, infrastructure monitoring platforms, and line-of-business application maintenance.

Responsibilities

Act as the highest escalation point for infrastructure, system, and network issues
Maintain, support, and continuously improve existing server, network, and endpoint infrastructure
Engineer and deploy new infrastructure solutions from design through implementation, aligned with business growth and modernization goals
Own and evolve the organization’s network infrastructure — including firewalls, routers, switches, VLANs, and VPNs — both maintaining current environments and designing improvements
Troubleshoot and resolve complex technical issues across servers, endpoints, and network systems
Manage and maintain Windows Server environments and Active Directory infrastructure
Monitor system and network performance using platforms such as Zabbix; deploy and manage infrastructure monitoring and alerting solutions
Architect and lead deployment of new infrastructure solutions aligned with business growth and modernization goals
Own and administer Microsoft Azure and hybrid cloud environments
Deploy, manage, and maintain endpoint environments using Microsoft Intune
Support and maintain line-of-business applications, including patching, updates, and vendor coordination
Support virtualization environments and ensure system availability and performance
Assist with infrastructure projects, including migrations, deployments, and integrations
Provide technical guidance and escalation support to Tier 1 and Tier 2 teams
Maintain technical documentation, network diagrams, and system procedures
Ensure security best practices, patch management, and system hardening standards are followed
Evaluate and recommend new technologies to improve infrastructure efficiency and reliability

Requirements:

Bachelor’s degree in Information Technology, Computer Science, or related field preferred
5+ years of experience in IT infrastructure, systems administration, or network engineering
Strong experience with Windows Server (2016/2019/2022) environments
Advanced knowledge of Active Directory, DNS, DHCP, and Group Policy
Strong networking experience including switches, routers, VLANs, VPNs, and firewalls – required
Experience troubleshooting both server and network infrastructure issues
Experience with virtualization (Hyper-V or VMware)
Hands-on experience with Microsoft Azure and hybrid cloud environments – required
Proficiency with endpoint management tools, specifically Microsoft Intune – required
Experience with infrastructure monitoring platforms such as Zabbix, or demonstrated ability and willingness to learn
Experience supporting and maintaining line-of-business applications, including patching and vendor coordination
Strong problem-solving and analytical skills
Ability to mentor and support Tier 1 and Tier 2 technicians
Certifications such as CCNA, Microsoft certifications (Azure, Intune), or equivalent preferred

Benefits: AFIC offers a competitive salary and a comprehensive benefits package to support you

Competitive Salary: Rewarding your expertise and experience
Financial Security: 401K with up to a 6% company match
Health & Wellness: Choice of Blue Cross Blue Shield PPO, HMO, or HSA plans, Dental and vision coverage, Access to telemedicine services
Growth/Stability: Over 12 consecutive years of profitable growth, confirmed by A+ Superior rating by A.M. Best
Work-Life Balance: Monday-Friday, 8 am-5 pm CST (Weekends- if needed)
Holidays: At Least 6 Paid Holidays
Paid Time Off (PTO): PTO that can be used for vacation, personal, or sick time
Personal Days: Separate personal days for sickness, family needs, appointments or personal matters
Employee Recognition: We celebrate work milestones to show appreciation for your contributions
Professional Growth: Paid training, state licensing reimbursement, and opportunities for advancement
Positive Culture: Enjoy our inclusive holiday events, employee referral bonuses, virtual team meetings, and more

Quick Apply

Refine Your Search

Windows Systems Engineer jobs in Chicago, IL

IT Technician Tier 3 – Senior Systems & Network Engineer

Lead Associate Principal, Infrastructure Innovation & Automation

Senior Windows Administator / Platform Engineer IV

Senior Windows Administator / Platform Engineer IV

Staff Performance Engineer, ServiceNow Platform

Infrastructure Engineer

Junior Network Engineer

Desktop Support Engineer

Senior Endpoint Systems Engineer (HYBRID: Chicago)

Infrastructure Engineer - Digital Network

Applications Engineer

IT Engineer

Storage Engineer

Sr Systems Engineer- Reliability Engineering and Operations

Senior Engineer

IT Site Reliability & Performance Engineer

Cloud Engineer (Remote)

Enterprise Engineer III

ASC IT Systems Engineer

Senior Infrastructure Engineer

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