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Weekend Msp System Engineer Jobs in Chicago, IL (NOW HIRING)

Aris Search

MSP Tier 2

Elgin, IL · On-site

$75K/yr

Tier 2 IT Support Engineer (MSP Environment - In Office + Field Work) Location: Elgin, IL Salary ... Monitor client systems and respond to alerts via RMM tools. * Participate in client projects such ...

Aris Search

MSP Tier 2

Elgin, IL

$75K/yr

Tier 2 IT Support Engineer (MSP Environment - In Office + Field Work) Location: Elgin, IL Salary ... Monitor client systems and respond to alerts via RMM tools. * Participate in client projects such ...

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 ... MSP experience ideal) Interviews are being conducted immediately so feel free to apply or contact ...

Noventech, Inc.

Senior Systems Engineer & Project Lead

Lombard, IL · On-site

$90K - $120K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

We are seeking a Senior Systems Engineer & Project Lead to join our growing IT team. This position ... Minimum 5 years of MSP experience, supporting multiple clients in diverse environments. * Proven ...

Noventech, Inc.

Senior Systems Engineer & Project Lead

Lombard, IL · On-site

$90K - $120K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

We are seeking a Senior Systems Engineer & Project Lead to join our growing IT team. This position ... Minimum 5 years of MSP experience, supporting multiple clients in diverse environments. * Proven ...

Impact Networking

Systems Engineer I

Bolingbrook, IL · On-site

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Troubleshoot system and application issues using documented procedures, available tools, and ... MSP experience preferred. Relevant internships, technical training, certifications, or equivalent ...

Impact Networking

Systems Engineer I

Bolingbrook, IL · On-site

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Troubleshoot system and application issues using documented procedures, available tools, and ... MSP experience preferred. Relevant internships, technical training, certifications, or equivalent ...

Impact Networking

Systems Engineer I

Hammond, IN · On-site

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Troubleshoot system and application issues using documented procedures, available tools, and ... MSP experience preferred. Relevant internships, technical training, certifications, or equivalent ...

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All JobsMsp System Engineer JobsWeekend Msp System Engineer JobsWeekend Msp System Engineer Jobs in Chicago, IL

Weekend Msp System Engineer information

See Chicago, IL salary details

$55.1K

$131.1K

$172K

How much do weekend msp system engineer jobs pay per year?

As of Aug 14, 2026, the average yearly pay for weekend msp system engineer in Chicago, IL is $131,050.00, according to ZipRecruiter salary data. Most workers in this role earn between $101,000.00 and $161,700.00 per year, depending on experience, location, and employer.

What are the typical challenges faced by a Weekend MSP System Engineer, and how can I prepare for them?

Weekend MSP System Engineers often encounter challenges such as handling urgent client issues with limited on-site support, managing multiple clients’ systems simultaneously, and troubleshooting critical incidents outside of regular business hours. To prepare, it’s important to develop strong remote problem-solving skills, be comfortable with a wide range of technologies, and communicate proactively with both clients and team members. Familiarity with documentation and escalation procedures can also help ensure smooth operations when unexpected situations arise.

What is a Weekend MSP System Engineer?

A Weekend MSP System Engineer is an IT professional who works for a Managed Service Provider (MSP), focusing on maintaining and supporting clients' IT systems specifically during weekends. Their responsibilities typically include monitoring servers and networks, troubleshooting issues, applying updates, and responding to client requests outside regular business hours. This role is vital for ensuring continuous IT support and minimizing downtime for clients who operate or require support over the weekend. Weekend MSP System Engineers often work remotely or in shifts to provide round-the-clock coverage. They must have strong technical skills, problem-solving abilities, and experience with various IT systems and platforms.

What is the difference between Weekend Msp System Engineer vs Network Support Specialist?

AspectWeekend Msp System EngineerNetwork Support Specialist
CertificationsCompTIA A+, Network+, Microsoft CertifiedCompTIA Network+, Cisco CCNA, Microsoft certifications
Work EnvironmentManaged Service Provider (MSP) settings, remote and on-site supportCorporate IT departments, help desks, remote troubleshooting
Industry UsageCommon in MSPs providing 24/7 IT supportCommon in enterprise and small business networks

The Weekend MSP System Engineer primarily focuses on maintaining and supporting client systems within MSP environments, often working remotely or on-site during weekends. In contrast, a Network Support Specialist typically works within corporate IT teams, providing network troubleshooting and support during regular hours. Both roles require similar certifications and technical skills but differ mainly in work setting and scheduling.

What are the key skills and qualifications needed to thrive as a Weekend MSP System Engineer?

To thrive as a Weekend MSP System Engineer, you need strong expertise in network administration, troubleshooting, and server management, typically supported by a degree in IT or related certifications such as CompTIA, Microsoft, or Cisco. Proficiency with remote monitoring and management (RMM) tools, ticketing systems, and cloud platforms like Azure or AWS is crucial. Excellent problem-solving skills, effective communication, and the ability to work independently during off-hours are key soft skills for this role. These skills ensure timely resolution of client issues and reliable IT infrastructure support during critical weekend hours.

What are the most commonly searched types of Msp System Engineer jobs in Chicago, IL?

The most popular types of Msp System Engineer jobs in Chicago, IL are:

Weekend Msp System Engineer jobs near you
Infographic showing various Weekend Msp System Engineer job openings in Chicago, IL as of August 2026, with employment types broken down into 67% Full Time, and 33% Part Time. Highlights an 93% In-person, and 7% Remote job distribution, with an average salary of $131,050 per year, or $63 per hour.

Systems Engineer - Infrastructure & Managed Services

Providence Management and Development Company Incorporated

Tinley Park, IL • On-site

$80K - $100K/yr

Full-time

Re-posted 23 days ago

Job description

Systems Engineer | Infrastructure & Managed Services

Do you thrive on solving technical puzzles, jumping between environments, and being the person clients trust when technology goes sideways? Do you enjoy a mix of support, projects, cloud, infrastructure, and “every day is different” energy? If so, keep reading.

We’re looking for a Systems Engineer to join our growing Managed Services team. This is not a narrow, siloed role where you only touch one platform all day. We’re looking for a well-rounded engineer who enjoys wearing multiple hats and helping small and mid-sized businesses stay secure, productive, and modern.

One day you may be troubleshooting a hybrid identity issue, the next you’re deploying Intune policies, assisting with a Microsoft 365 migration, or helping standardize a client’s infrastructure. If variety keeps you motivated, you’ll fit right in.

What You’ll Be Doing
  • Supporting and troubleshooting a variety of SMB client environments
  • Working service tickets, escalations, proactive maintenance, and project work
  • Managing Windows Server environments, Active Directory, Group Policy, DNS, DHCP, and file services
  • Supporting Microsoft 365 technologies including:
    • Exchange Online
    • SharePoint Online
    • Teams
    • OneDrive
    • Entra ID
    • Intune
  • Assisting with Microsoft 365 migrations and modernization initiatives
  • Supporting virtualization platforms like VMware and Hyper-V
  • Troubleshooting networking issues involving VPNs, firewalls, switches, wireless, and WAN/LAN connectivity
  • Helping onboard new clients and standardize environments
  • Maintaining clean documentation and accurate records
  • Collaborating with internal teams, vendors, and clients
  • Participating in occasional on-call escalation support
What Makes Someone Successful in This Role

You’re the kind of person who:

  • Likes solving problems and figuring things out
  • Can juggle multiple priorities without panicking
  • Communicates well with both technical and non-technical people
  • Understands that great customer service matters just as much as technical ability
  • Enjoys learning new technologies and adapting quickly
  • Takes ownership of issues instead of passing them around
What You Bring to the Table
  • MSP experience supporting multiple clients and environments
  • Strong Windows infrastructure knowledge
  • Experience with Microsoft 365 and hybrid environments
  • Familiarity with virtualization platforms such as VMware and Hyper-V
  • Networking fundamentals including TCP/IP, VPNs, switching, firewalls, and wireless
  • Strong troubleshooting and analytical skills
  • Experience working in ticket-driven, SLA-focused environments
  • Excellent documentation and organizational habits
Qualifications
  • Bachelor’s degree in IT, Computer Science, or equivalent real-world experience
  • 3+ years of systems engineering or administration experience in an MSP environment
  • Experience supporting Microsoft 365 environments and Windows infrastructure
  • Ability to independently diagnose and resolve complex technical issues
Bonus Points For
  • Microsoft certifications (AZ-900, MS-900, SC-900, MD-102)
  • VMware, networking, or security certifications
  • Experience with RMM tools, PSA platforms, and documentation systems
The Details
  • Full-time position
  • Occasional onsite client visits may be required
  • Participate in on-call rotation
  • Fast-paced, collaborative MSP environment
  • A role where your ideas, technical skills, and initiative actually matter
Why You’ll Love It Here

We know MSP life can be chaotic, but we also know it can be incredibly rewarding with the right team. We value collaboration, accountability, strong communication, and people who genuinely enjoy technology. You’ll work alongside a team that supports each other, solves problems together, and believes work can be both professional and enjoyable.

If you’re looking for a role where no two days are the same and your technical skills can continue to grow, we’d love to hear from you.