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Remote Level 2 It Support Jobs in Chicago, IL (NOW HIRING)

Sterling Engineering Inc.

Director of IT

Chicago, IL · On-site +1

Title : Director of IT - (Manufacturing and Industrial) Infrastructure and Delivery Location ... remote users. * Partner with operational technology teams to support secure IT/OT integration ...

Sentinel

IT Security Engineer

Downers Grove, IL · On-site +1

$70K - $100K/yr

The Sentinel IT Security Engineer will be responsible for supporting, administering ... This position can work remote within the United States and occasional travel to Downers Grove, IL ...

Sentinel

IT Security Engineer

Downers Grove, IL · On-site +1

$70K - $100K/yr

Responsibilities The Sentinel IT Security Engineer will be responsible for supporting ... This position can work remote within the United States and occasional travel to Downers Grove, IL ...

Sentinel

IT Security Engineer

Downers Grove, IL · On-site +1

$70K - $100K/yr

Responsibilities The Sentinel IT Security Engineer will be responsible for supporting ... This position can work remote within the United States and occasional travel to Downers Grove, IL ...

Natus Medical Incorporated

IT Director

Schaumburg, IL · On-site +1

TSA to support business growth. * Risk Management: Identify, assess, and mitigate risks related to ... Bachelor's Degree or an equivalent level of education and experience in IT, Computer Science ...

Small Business Administration

IT Specialist

Chicago, IL · On-site +1

$140K - $182K/yr

Leads and mentors project teams composed of technical specialist, analysts, and support staff ... There is no education substitution for this grade level. If you are a current career or career ...

Sralab

IT Security Analyst

Chicago, IL · Remote

Provides emergency, after-hours and weekend support on a rotational basis to respond to priority ... Reporting Relationships Reports to Manager of IT Security Operations Remote work within the ...

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Remote Level 2 It Support information

See Chicago, IL salary details

$15

$28

$46

How much do remote level 2 it support jobs pay per hour?

As of Aug 22, 2026, the average hourly pay for remote level 2 it support in Chicago, IL is $28.90, according to ZipRecruiter salary data. Most workers in this role earn between $23.03 and $32.45 per hour, depending on experience, location, and employer.

What is a remote level 2 IT support?

Remote Level 2 IT Support professionals provide technical assistance to users by resolving more complex IT issues that cannot be solved by Level 1 support. They work remotely to troubleshoot software, hardware, and network problems, often using remote access tools and advanced diagnostic methods. These specialists may also escalate unresolved issues to higher-level engineers, maintain documentation, and contribute to system improvements. Strong communication skills and in-depth technical knowledge are essential for this role.

What skills and qualifications are needed for remote level 2 IT support?

To excel as a Remote Level 2 IT Support specialist, you need advanced troubleshooting skills, strong knowledge of operating systems and networks, and usually a relevant IT degree or certifications like CompTIA A+ or Microsoft Certified: Windows Support. Familiarity with remote desktop tools, ticketing systems, and diagnostic utilities is essential for resolving complex user issues. Outstanding communication, patience, and problem-solving abilities help build trust and efficiently assist users remotely. These competencies ensure timely resolution of technical problems, minimize downtime, and maintain high levels of user satisfaction in a distributed work environment.

What challenges do remote level 2 IT support professionals face and how can they address them?

Remote Level 2 IT Support professionals often encounter challenges such as troubleshooting complex technical issues without physical access to devices, managing multiple support tickets simultaneously, and communicating clearly with end-users who may have varying levels of technical knowledge. To address these challenges, it's important to leverage remote diagnostic tools, maintain organized ticket management, and develop strong communication skills to guide users through solutions. Regular collaboration with Level 1 and Level 3 support teams also helps ensure escalated issues are resolved efficiently and knowledge is shared across the team.

What is the difference between Remote Level 2 It Support vs Remote Help Desk Technician?

AspectRemote Level 2 It SupportRemote Help Desk Technician
CertificationsCompTIA A+, Network+; Microsoft CertifiedCompTIA A+; Basic certifications
Work EnvironmentTechnical support, troubleshooting complex issuesCustomer support, basic troubleshooting
Employer UsageIT departments, managed service providersHelp desk services, IT support companies
Search IntentTechnical problem-solving, advanced supportBasic support, customer service

Remote Level 2 It Support involves handling more complex technical issues, requiring advanced certifications and troubleshooting skills. In contrast, Remote Help Desk Technicians focus on basic customer support and initial troubleshooting. Both roles are essential in IT support but differ in complexity and responsibilities.

What are the most commonly searched types of Level 2 It Support jobs in Chicago, IL?

The most popular types of Level 2 It Support jobs in Chicago, IL are:

What are popular job titles related to Remote Level 2 It Support jobs in Chicago, IL?

For Remote Level 2 It Support jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote Level 2 It Support jobs in Chicago, IL look for?

The top searched job categories for Remote Level 2 It Support jobs in Chicago, IL are:

Remote Level 2 It Support jobs near you
Infographic showing various Remote Level 2 It Support job openings in Chicago, IL as of August 2026, with employment types broken down into 74% Full Time, 9% Part Time, and 17% Contract. Highlights an 100% Remote job distribution, with an average salary of $60,105 per year, or $28.9 per hour.

Technical IT Support Specialist - Chicago, IL

Buckeye Mountain

Chicago, IL • Remote

Full-time

Posted 23 days ago

Job description

The Role

We are looking for a technically minded IT support professional who can bridge the gap between end-user helpdesk and senior engineering. You are not a traditional help desk — you understand systems well enough to triage a network issue, interpret a monitoring alert, and know whether to resolve it yourself or get the right engineer involved. You will own monitoring across our network, cloud, and NaaS environments, serve as the first-level escalation for technical issues, and support endpoint and device management operations. When something is wrong somewhere in our environment, you will often be the first to know.

What You'll Own

Monitoring & Observability

• Monitor network, cloud, and NaaS environments using observability and alerting platforms — Splunk, cloud monitoring consoles, and remote management tools

• Own NaaS site monitoring — track link health, power telemetry, and connectivity status for all active remote sites

• Respond to and triage monitoring alerts; resolve within your scope or escalate with full context to the appropriate engineer

• Manage NaaS firmware and configuration changes for live sites in coordination with the Field Engineering team

Technical First-Level Support

• Serve as the first technical escalation point for issues routed up from the helpdesk — network connectivity, application access, system performance

• Perform first-level network troubleshooting — diagnosing issues before escalating to the Senior Network Engineer

• Own the technical ticket queue for infrastructure-adjacent issues, ensuring nothing sits unrouted

• Contribute to SLA compliance by maintaining response time discipline and clear ticket documentation

Endpoint & Device Support

• Assist the Identity & Endpoint Systems Administrator with device enrollment (Intune, Apple Business Manager), compliance policy deployment, and device imaging

• Support OS patching cycles for Windows and Linux systems under direction of the Systems & Application Engineer

• Contribute to knowledge base and troubleshooting documentation for recurring issues

What We're Looking For

Required

• 3+ years in an IT support, NOC, or junior systems administration role

• Working knowledge of networking concepts — TCP/IP, DNS, VLANs, subnetting, basic firewall behavior

• Experience with monitoring and alerting platforms — Splunk, PRTG, Datadog, Zabbix, or equivalent

• Familiarity with Microsoft Intune or another MDM platform for device enrollment and policy deployment

• Experience supporting Windows environments at a systems level — not just end-user troubleshooting

• Strong communication skills — ability to escalate clearly, document concisely, and keep stakeholders informed during incidents

• Experience with a ticketing platform (Jira Service Management preferred)

Preferred

• Experience monitoring or supporting remote or field-deployed network infrastructure

• NaaS, managed connectivity, ISP, or telecom support background

• Splunk experience — dashboards, searches, alert configuration

• Basic scripting ability — PowerShell or Python for automation or log parsing

• Linux command-line proficiency at a support level

Details

• Location: Remote — must be available during core US business hours

• Travel: Minimal

• Employment type: Full-time