Key Takeaways
- For offices under about 75 people, outsourcing usually costs less than one full-time IT hire.
- An in-house hire knows your business best but can’t cover every skill or every day of the year.
- Co-managed IT combines both: your own person plus an outside team.
- Compare total cost, including benefits, tools, training and the cost of gaps.
Sooner or later every growing Chicago business asks the same question: hire an IT person, or hand IT to an outside team through managed IT services? Both can work. The right answer depends on your size, your systems and how much risk you can live with.
This guide compares the two honestly, with typical Chicago numbers, and shows when outsourced IT support, an in-house hire or a mix of both makes the most sense. It also gives you a calculator, so you can test the math against your own headcount.
The Real Cost of Each Option
Here is a typical first-year comparison for a 25-person Chicago office.
| Cost item | In-house IT hire | Outsourced IT (25 users) |
|---|---|---|
| Salary | $75,000 to $95,000 | Included |
| Benefits & payroll taxes | $18,000 to $28,000 | Included |
| Tools & software | $5,000 to $12,000 | Included |
| Training & certifications | $2,000 to $5,000 | Included |
| Recruiting | $10,000 to $18,000 | None |
| Service fees | None | $37,500 to $52,500 |
| First-year total | $110,000 to $158,000 | $37,500 to $52,500 |
The figures are typical estimates for an experienced IT support or systems administrator role in Chicago and a fully managed plan at $125 to $175 per user per month. Salary is the line that varies most, and the Bureau of Labor Statistics wage data for the Chicago metro area is a good reference when you budget a hire. The Chicago pricing guide explains what moves the per-user rate on the outsourced side.
The Costs That Hide Behind the Salary
Benefits and payroll taxes typically add a quarter or more to a salary. On top of that, your IT person needs monitoring software, a ticketing system, backup tools and training to stay current, which a provider spreads across many clients. Recruiting is the cost people forget most: an agency fee or weeks of a manager’s time, plus the months before a new hire knows your systems.
What Outsourcing Does Not Include
A fair comparison also counts what sits outside a monthly plan. Microsoft 365 and other software licenses, new laptops and network hardware, and one-off projects such as an office move are usually billed separately, whether you outsource or hire. They belong in both budgets, so they rarely change which option wins, but they keep the comparison honest.
Benefits, tools, training and recruiting add a large share on top of an IT salary, while an outsourced fee includes them.
Run Your Own Numbers
Enter your headcount, the salary you would offer and a per-user rate to compare one year of each option.
First year, in-house vs. outsourced$121,500 vs. $45,000In-house includes about 27% for benefits and taxes plus $8,000 for tools and training, before recruiting.
The break-even point usually sits somewhere between 60 and 90 employees, depending on the salary you need to offer and the plan level you choose. Above that, a hire starts to make financial sense, although coverage and skills still argue for outside help.
Where Each Option Wins
Hiring Makes Sense When IT Is Constant
A full-time hire pays off when there is enough daily, hands-on work to fill a week, every week, and when that work depends on knowing your business inside out.
- You have 100+ staff in one location
- You run custom or in-house software
- Technology is part of what you sell
- You need someone on-site all day
Outsourcing Makes Sense for Most Offices
For teams without IT staff, an outside team covers more skills for less money than one salary, and nobody has to recruit, train or replace anyone.
- You have fewer than about 75 staff
- Nobody on your team owns IT today
- You need security, cloud & network skills
- You want a predictable monthly cost
The Mix Works When Your IT Person Is Stretched
If you already have one or two IT people, adding an outside team is often better than hiring more, because you buy coverage and specialist skills instead of another generalist.
- Your IT staff are overloaded
- Nobody covers vacations or nights
- Security monitoring is missing
- Big projects keep slipping
Teams under 25 people should look at small business IT support, which is priced and sized for that stage.
The break-even point usually sits between 60 and 90 employees, depending on salary and plan level.
In-House vs. Outsourced, Side by Side
| Factor | In-house IT | Outsourced IT |
|---|---|---|
| Knows your business | Deeply, over time | Learns it during onboarding, then documents it |
| Availability | Business hours, minus time off | Every business day, plus 24/7 monitoring |
| Range of skills | One person’s strengths | Help desk, security, cloud and network |
| Cost | Salary, benefits, tools, training | One predictable monthly fee |
| Security coverage | Depends on the person’s time | Monitoring and patching on a schedule |
| Growing the team | Another hire, months away | Add users to the plan |
An in-house person wins on familiarity and walk-up questions. An outside team wins on coverage, breadth and predictability. Which of those matters more depends on how your office works day to day.
Risks People Forget
The Single Point of Failure
If your only IT person leaves, passwords, setups and vendor contacts often leave with them. Vacations and sick days create smaller versions of the same gap. Whatever you choose, insist on written documentation that someone else could pick up tomorrow.
The Security Skills Gap
Phishing, invoice fraud and ransomware hit businesses of every size, and the FBI’s Internet Crime Complaint Center tracks billions in reported losses every year. One generalist rarely has time to watch alerts around the clock, which is why security monitoring is often the first thing companies outsource, even when they keep an internal IT person.
The question to ask is simple: who is watching your systems at 2 a.m. on a Sunday? If the honest answer is nobody, that gap exists whether you hire or not, and closing it usually costs far less as part of a monitored plan than as a second full-time salary.
Provider Lock-In
The biggest outsourcing risk is choosing the wrong provider: unclear scope, slow response or contracts that are hard to exit. Keep admin access in your own hands and read the exit terms before you sign. The guide to choosing an IT provider in Chicago shows what to check.
Three Chicago Companies, Three Answers
The right model depends less on industry than on size, systems and how much hands-on work there is. These three examples show how the decision usually plays out.
A 15-Person Architecture Studio in River North
Large drawing files, fast Wi-Fi and a handful of powerful workstations, but nobody on staff who owns IT. A full-time hire would cost more than the rest of the studio’s technology budget combined. An outsourced plan covers the help desk, backups of project files and security for a fraction of that, with on-site visits when a workstation or plotter needs attention.
A 70-Person Manufacturer in Elk Grove Village
One long-serving IT manager knows the shop-floor systems better than anyone, but spends the day resetting passwords and has not taken a real vacation in years. Replacing that knowledge would be risky, so the company keeps its manager and adds co-managed support for the help desk, after-hours monitoring and patching. The manager finally has time for the ERP upgrade that kept slipping.
A 180-Person Distributor in the Western Suburbs
At this size, a small internal team of two or three makes financial sense, especially with warehouse systems that need someone on-site every day. Even here, security monitoring around the clock is outsourced, because staffing a 24/7 security function internally would cost far more than the service.
Notice the pattern: the smaller the company, the more it gains from outsourcing everything. The larger it gets, the more it keeps in-house, but almost nobody covers every skill alone.
Smaller companies gain most from outsourcing everything, while larger ones keep more in-house but still buy specialist help.
The Hybrid Route: Co-Managed IT
Many Chicago companies land in the middle. They keep one or two internal IT people for daily decisions and projects, and add an outside team for the help desk, after-hours coverage and security monitoring. That model is called co-managed IT, and it is usually priced below a full outsourced plan because your team keeps part of the work.
It works best when roles are written down from the start: which tickets go where, who handles which alerts and who has admin access to what. Without that, two teams can leave the same gap.
A good co-managed setup also shares the same tools. When your internal person and the outside team work from one ticketing system and one set of documentation, nobody has to ask what the other one did, and handovers at night or on weekends happen without a phone call.
Shared tools and written roles keep a co-managed setup from leaving the same gap twice.
How to Switch Without Losing a Day of Work
- Secure the admin accounts. Make sure the company, not one person, owns Microsoft 365, the domain, the firewall and backups.
- Document before anyone leaves. Capture passwords, vendors, licenses and network details while your current person is still around.
- Move support in stages. Start with monitoring and backups, then hand over the help desk once staff know how to reach it.
- Review after 30 days. Check the first monthly report and adjust the scope while the switch is fresh.
If your IT person is leaving on short notice, start with step one the same day. Losing access to a domain registrar or a firewall login is the one mistake that turns a simple switch into weeks of recovery work.
Securing admin accounts first is the single step that prevents most switching problems.
How to Choose
Before you decide, answer five questions honestly. They settle most cases faster than any spreadsheet.
- How much hands-on work is there? If someone would be busy on-site all day, every day, a hire starts to make sense.
- Which skills do you need? Count help desk, security, cloud and networking. One person rarely covers all four well.
- What happens during a vacation? If the answer is “nothing gets fixed,” you need coverage beyond one person.
- How fast are you growing? Adding users to a plan takes days. Adding IT staff takes months.
- Who owns the passwords today? If it is one person, fix that first, whichever option you choose.
Count your staff, list the skills you need and price both options for a full year, including the gaps. Under about 75 people with no IT staff, outsourcing usually wins. With one or two IT people already, co-managed IT usually wins. With constant on-site work and custom systems, a hire can make sense.
Need help only now and then? IT support services may be all you need for now, and you can move to a monthly plan as the office grows.
FAQs
Is outsourced IT less secure than in-house IT?
Not usually. A good provider brings security tools and specialists that most single IT hires don’t have. Ask how they monitor threats and who has access to your systems.
Can I switch from in-house to outsourced IT later?
Yes. Many companies outsource after an IT person leaves. The switch goes much smoother if systems and passwords are documented before they go.
What happens to our IT person if we outsource?
Many companies keep them and move to co-managed IT, so they focus on projects while the outside team handles daily support and monitoring.
How much does an IT person cost in Chicago?
Expect roughly $75,000 to $95,000 in salary for an experienced support or systems administrator role, plus benefits, tools and training.
Is outsourcing only for small businesses?
No. Companies of every size outsource some or all of their IT. Larger companies more often use co-managed IT alongside their internal team.
Reid Callahan
Editorial Director, Ping Chicago
Reid leads the Ping Chicago editorial team and works with our technicians to turn real support tickets, office moves and security reviews into plain-English guides for Chicago business owners. Born and raised in Chicago, he has spent more than 15 years in IT services, starting on the help desk and later running support and network projects for law firms, medical practices and manufacturers from the Loop to the western suburbs. He holds Microsoft 365 and CompTIA Security+ certifications and has helped hundreds of local offices move to the cloud. Today he focuses on how AI tools like Microsoft Copilot can save small teams time without putting company data at risk, and every guide he writes is checked by a working technician before it goes live.