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Last updated October 2026
The quick answer: For most Chicago-area businesses with fewer than about 30 users, outsourcing IT costs less than hiring one full-time IT person, and it covers far more skills. Between about 30 and 60 users, the costs are similar. Above that, outsourcing can cost as much as one hire, but it gives you a whole team instead of one person. Many companies with an internal IT person get the best of both with co-managed IT.
If your company has 20 to 250 employees, sooner or later someone asks: “Should we just hire an IT person?” Maybe your IT manager just gave notice. Maybe the office manager has been “doing IT” for years and is worn out. Here’s a plain comparison: what each option costs, what you get, and how to decide.
What it costs to hire IT staff in the Chicago area
The U.S. Bureau of Labor Statistics (BLS) publishes pay data for the Chicago-Naperville-Elgin area. As of May 2025:
- Network and computer systems administrators (the typical “IT person”): median pay of $103,170 a year.
- Computer and information systems managers (IT managers and directors): average pay of $184,810 a year.
Salary isn’t the whole cost. Benefits such as health insurance, retirement and paid leave make up about 30% of total compensation for private-industry workers (BLS, June 2026). That adds roughly 43% on top of pay.
| Role | Pay (BLS, Chicago area) | Estimated total cost with benefits |
|---|---|---|
| IT generalist / systems administrator | $103,170 | about $147,000 a year |
| IT manager | $184,810 | about $264,000 a year |
Costs that don’t show up in salary:
- Recruiting and hiring time. Good IT people are hard to find, and a bad hire is expensive.
- Tools. Security software, monitoring, backup and help desk systems are usually separate purchases.
- Training. Security threats change constantly, and someone has to keep up.
What it costs to outsource
CTI Technology publishes its pricing: $200 to $400 per user per month on one flat-rate plan. Where you fall depends mostly on your security and compliance needs.
| Company size | Managed IT cost per year |
|---|---|
| 20 users | $48,000 to $96,000 |
| 50 users | $120,000 to $240,000 |
| 100 users | $240,000 to $480,000 |
The plan includes help desk support, Microsoft 365 administration, network management, backup and disaster recovery, and cybersecurity, including 24/7 security monitoring & emergency response. See our pricing page.
Where the break-even falls: one IT generalist costs about $147,000 a year with benefits. At $200 to $400 per user per month, that equals managed IT for roughly 30 to 60 users, before you add the tools that person would still need.
Cost isn’t the only difference
At 100 users or more, a managed IT plan can cost as much as, or more than, one in-house person. So why do larger companies still outsource? Because one person can’t be everything.
| One in-house IT person | Managed IT provider | |
|---|---|---|
| Coverage | Out when they’re sick, on vacation or quit | A team covers your account |
| Skills | One person’s knowledge | Help desk, network, security and cloud specialists |
| Security | Depends on one person keeping up | Dedicated security tools and monitoring |
| After hours | Usually no one | 24/7 security monitoring & emergency response |
| Planning | Often too busy fixing things | A dedicated Account Manager and quarterly business reviews |
| Knows your business | Yes, deeply | Learns it during onboarding, and documents it |
| Onsite | Always in the building | Same-day onsite support possible across Chicago and the suburbs |
The in-house person’s biggest strength is being in the building and knowing your people. That’s real. The biggest risk is that everything about your IT lives in one person’s head.
Your IT manager is leaving. Now what?
This is one of the most common reasons companies call us. If your IT person has given notice, do these four things right away:
- Get the admin passwords. Make sure the company, not just the employee, controls the logins for Microsoft 365, your domain name, your firewall and your backups.
- Ask for documentation. A list of systems, software, vendors, renewal dates and anything “only they know how to fix.”
- Check your backups. Confirm backups are running and that someone has tested a restore recently.
- Line up help before their last day. A handover with your departing person in the room is much easier than one without.
How fast can a managed IT provider take over? At CTI Technology, a typical onboarding is finished within 15 to 30 days of the kick-off call. That covers documenting your systems, installing security and monitoring tools, and setting up help desk access. Most of it happens in the background, so your team keeps working. Read more about our onboarding process, or see how to switch IT providers without the headaches.
Signs you need outside IT help
- Your “IT person” is really an office manager or owner doing it on the side.
- Problems get fixed, but nothing gets planned. No budget, no roadmap.
- You’ve had a scare: a phishing email that got through, a lost laptop, a backup that didn’t work.
- Your cyber insurance company or a big client sent a security questionnaire you couldn’t answer.
- You’re growing, and IT can’t keep up with new hires and new offices.
A note for law firms
Law firms face one extra question: can one person meet your duty to protect client information? ABA Model Rule 1.6(c) and Illinois Rule 1.6(e) require “reasonable efforts” to prevent unauthorized access to client data. In practice that means multi-factor authentication, encryption, tested backups and a written incident response plan, kept up to date. That’s a lot for one IT generalist to own alone. See our IT guide for Chicago law firms.
When co-managed IT makes sense
You don’t have to choose one or the other. Many companies keep their internal IT person and bring in a provider for the rest: help desk overflow, security monitoring, projects and backup. Your person stays focused on what they know best, and they finally get to take a vacation. Learn more about co-managed IT.
If you need high-level planning but not a full-time executive, a fractional CIO/CTO can fill that gap. See IT strategy and fractional CIO.
Frequently asked questions
Is it cheaper to outsource IT or hire an IT person?
For most businesses under about 30 users, outsourcing costs less. A Chicago-area systems administrator earns a median of $103,170 (BLS, May 2025), or about $147,000 a year with benefits. CTI Technology’s managed IT runs $200 to $400 per user per month, so one hire equals managed IT for roughly 30 to 60 users. Above that, coverage, security and depth of skills become the deciding factors.
How much does an IT manager cost in Chicago?
According to the Bureau of Labor Statistics, computer and information systems managers in the Chicago-Naperville-Elgin area earned an average of $184,810 in May 2025. With benefits, which average about 30% of total compensation, the full cost is roughly $264,000 a year. That doesn’t include recruiting, training or the security and monitoring tools the role needs.
Our IT manager is leaving. How quickly can a managed IT provider take over?
At CTI Technology, a typical onboarding is completed within 15 to 30 days of the kick-off call. Before your IT person leaves, make sure the company controls all admin passwords, ask for written documentation, and confirm backups are working. Starting the handover while they’re still there makes the transition much smoother.
What’s the difference between managed IT and co-managed IT?
With managed IT, an outside provider handles all of your IT. With co-managed IT, you keep your internal IT staff and the provider fills the gaps, such as help desk overflow, security monitoring, backup and larger projects. Co-managed IT works well for companies that already have an IT person but need more depth or coverage.
Will we lose onsite support if we outsource?
Not necessarily. CTI Technology is headquartered in Elgin and can provide same-day onsite support across Chicago and the suburbs when a problem can’t be fixed remotely. Most issues are solved remotely. CTI’s average response time is under one hour during help desk hours, Monday through Friday, 8 a.m. to 5 p.m. Central.
Does outsourced IT include support after hours?
CTI Technology’s help desk is available Monday through Friday, 8 a.m. to 5 p.m. Central. Outside those hours, 24/7 security monitoring & emergency response watches for threats such as ransomware and suspicious sign-ins and responds when something needs immediate attention. Routine requests are handled the next business day.
About CTI Technology
CTI Technology has provided managed IT and cybersecurity to Chicago-area businesses since 2004. We’re headquartered in Elgin, we’re a Microsoft AI Cloud Partner, we publish our pricing, and 98.5% of our clients stay with us.
Not sure which fits your business?
We’ll give you a straight answer, even if it’s “keep your IT person.” Schedule a 15-minute call with our team, or call (847) 888-1900 (Chicago: 312-922-8600).
Aaron Kane
Why Is CTI Technology The Best Choice For IT Services In The Chicagoland Region?
“Great pricing, even better service. Highly recommended!”
Great pricing, even better service. Highly recommended!”
Guido Arquilla
“Great IT company for our business! Highly recommended.”
“Great IT company for our business! Highly recommended.”
Brian Coli
“CTI is a great company and I would not trust my IT services to anyone else.”
CTI is a great company and I would not trust my IT services to anyone else.
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