$120k - $140k
endpoint management Provide advanced troubleshooting and escalation support Maintain infrastructure documentation and standard processes... ...Work Environment Full-time, onsite role Hands-on IT and infrastructure enviro…
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.
133
Open roles today
$21–$50/hr
Typical pay range
$70k
Median, full-time
6
Fresh in this list
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01
Open it support specialist roles
12 shown of 133 · sorted by freshness
with a highly available enterprise technology environment and a significant on-premise infrastructure footprint. The internal IT team supports business-critical systems across networking, virtualization, servers, storage…
$55k - $60k
is expected to be able to provide advanced desktop and end user support as well as assist with the support of server and network environments... ...resource preferred. ~1-2 years' experience supporting backend IT infrast…
traded on Euronext Brussels (AGFB). At Agfa HealthCare, we support healthcare professionals across the globe to transform the delivery... ...of care. Our focus is 100% on providing best-of-suite Imaging IT software solut…
$25.96 - $33.65 per hour
Description Company SDI Presence LLC is a leading IT services firm that leverages its strong team presence to advance clients... ...connect with us on Xand LINKEDIN. Summary The Desktop Support Specialist is responsible…
Summary Are you excited to help power the productivity of every Yelper globally? The IT Helpdesk team provides tech support to our Yelp offices worldwide. We solve technical challenges daily while providing customer supp…
$45k - $50k
university of uncommon character and enduring excellence, where faith, learning, and service meet. Position Summary The IT Support Specialist provides Tier 1 support for all campus technology systems and platforms includ…
$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…
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…
$93k - $114k
Description Company SDI Presence LLC is a leading IT services firm that leverages its strong team presence to advance clients toward... ..., laptops, and mobile devices as well as other technologies to support the organi…
$100k - $125k
innovation and a willingness to challenge consensus. As a Trade Support Specialist , you’ll provide middle office support to a group of trading... ...’ needs Adopt, integrate, and promote new technology as it becomes ava…
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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
04
Systems Administrator
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