$45.76k
Take ownership of the sites ticketing system and resolve technical support issues promptly and professionally. Communicate clearly with... ...Windows Hardware More: We are hiring a full-time Site IT Technician for in-per…
Engineering & IT · Chicago, IL
IT Support Specialist jobs in Chicago, IL
IT support specialists are the first call when technology breaks — diagnosing hardware, software, and account issues, and keeping employees productive. A common entry point into IT careers.
141
Open roles today
$21–$50/hr
Typical pay range
$70k
Median, full-time
8
Fresh in this list
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01
Open it support specialist roles
12 shown of 141 · sorted by freshness
$43.33 per hour
job summary: We are seeking an experienced IT Change Management Specialist to partner across enterprise teams and lead large-scale change initiatives centered on AI Literacy and tool adoption. In this role, you will desi…
$90.13k - $110.93k
business unit leaders, HR, and corporate communications to support leadership role modeling and sustain change goals.... ...Support Excel More: We are seeking an experienced IT Change Management Specialist to lead large-…
$45k - $55k
research laboratory services and specialized pre-clinical studies in support of pharmaceutical and biotechnology products.Position/Job... ...changes, validation/UAT, and new functionality in partnership with IT and relev…
$45k - $56k
IT Support Specialist Employment Type: Full-Time, Permanent Work Arrangement: Hybrid Experience Required: 0-2 years Salary: $45,000-$56,000/year Job Summary We are hiring an IT Support Specialist to maintain and troubles…
$26 - $32 per hour
Full-Time | Excellent Benefits Are you a hands-on IT professional who enjoys troubleshooting technology, supporting users, and helping keep systems running smoothly? Labelmaster is seeking an IT Support Specialist to pro…
We are seeking a hands-on Systems & Network Administrator to support and maintain our server, virtualization, storage, and network infrastructure... ...-service skills. Ability to lift, move, rack, and connect IT equipme…
range of activities related to the administration and support of the various computer systems, as well a preparing... ...Operates under the direct general supervision of the IT Systems Coordinator. The Systems Specialist…
$65k - $85k
Position Summary The IT Support Specialist provides hands-on and remote technical support to attorneys, staff, and business professionals across the firm. Reporting to the Manager of IT Services, this position serves as…
We are seeking an experienced Tonkean Support Engineer to provide technical support, administration, troubleshooting, and enhancement of Tonkean-based applications, workflows, and integrations. The ideal candidate will h…
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 t…
$45k - $50k
clients. Job Description: We are seeking a skilled Warehouse IT Technician with experience in IT inventory management. The ideal... ...be instances where field IT technician duties are required to support our clients wit…
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What it support specialists earn in Chicago
Hourly first — that's how the offer arrives
| Experience | Hourly | Annual, full-time |
|---|---|---|
| Entry level | $21–$28 | $43k–$59k |
| Mid level | $28–$39 | $59k–$81k |
| Senior | $38–$50 | $78k–$103k |
Adjusted for the Chicago market from national ranges.
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What employers ask for
The skills these listings keep naming
Windows and macOS troubleshootingTicketing systems (Jira, ServiceNow)Active Directory / Azure AD basicsHardware setup and repairMicrosoft 365 / Google WorkspaceNetworking basicsPatient, clear communicationDocumentationRemote support tools
04
Interview questions worth rehearsing
With the thing the interviewer is actually listening for
A user says their computer is slow. Walk me through your troubleshooting.
Ask clarifying questions first, then check the obvious in order: resource usage, startup programs, updates, disk health. The structured approach is the answer.
How do you explain a technical fix to a frustrated non-technical user?
Show empathy first, plain language second, and confirmation the user is unblocked. They are hiring your bedside manner as much as your knowledge.
How do you prioritize when multiple tickets come in at once?
Impact and urgency: outages affecting many people before individual inconveniences, with communication to those who wait. Mention using SLAs if you have worked with them.
What do you do when you cannot solve an issue yourself?
Timebox, document what you tried, and escalate with full context. Knowing when to escalate is a strength, not a failure.
A user asks you to bypass a security policy to work faster. What do you say?
Decline kindly, explain the reason, and offer a compliant alternative or escalate the policy question. They are checking your judgment under social pressure.
How do you keep track of recurring issues?
Talk about ticket tagging, knowledge-base articles, and flagging patterns to reduce repeat work. Turning tickets into documentation shows initiative.
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Resume tips that move the needle
For it support specialists specifically — generic advice costs you here
01
Include your ticket metrics: volume handled, first-contact resolution rate, or satisfaction scores if tracked.
02
List the exact systems supported (Windows 11, macOS, M365, AD) because postings filter on them literally.
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Show knowledge-base or documentation contributions; they signal you reduce future tickets, not just close today's.
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CompTIA A+ or similar certifications materially help at entry level — list in-progress ones too.
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Mention the environment scale (number of users or sites supported) to give your experience context.
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Where this role goes
Typical progression
01
Help Desk Technician
02
IT Support Specialist
03
Senior IT Support Specialist
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Systems Administrator
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