How Much Should a Small Business Pay for IT Support in Chicago?

The two main pricing models

Most IT support falls into one of two categories. Break-fix means you call when something goes wrong and pay an hourly rate for the time it takes to fix it. Managed IT means you pay a flat monthly fee and your provider handles monitoring, maintenance, and support on an ongoing basis.

Break-fix is unpredictable. Your monthly bill could be zero or it could be $3,000, depending on what breaks. Managed IT is predictable. You know exactly what you are spending each month.

There is a third option, which is hiring an in-house IT person. For a small business in Chicago, a full-time IT employee costs $60,000 to $90,000 per year in salary alone, plus benefits. Most businesses with fewer than 50 employees cannot justify that cost.

What managed IT support typically costs in Chicago

For small businesses in Chicago with 5 to 50 employees, managed IT support typically runs between $100 and $250 per user per month, depending on what is included. At the lower end, you are usually getting basic monitoring and helpdesk access. At the higher end, you are getting proactive security management, backup monitoring, vendor management, and on-site support.

A 10-person firm might pay $1,000 to $2,500 per month for comprehensive managed IT. That sounds like a lot until you compare it to the cost of a single significant IT failure, a ransomware attack, or hiring even a part-time IT employee.

Some providers charge per device instead of per user. If your team has multiple devices each, per-user pricing is usually better. If your team is lean on devices, per-device can work out lower. Ask for both calculations.

What should be included

• 24/7 monitoring of your systems so problems are caught before they become outages
• Helpdesk support with a defined response time, not just a ticket queue with no SLA
• Security patching and software updates handled on a regular schedule
• Endpoint protection across all covered devices
• Backup monitoring to confirm your backups are actually running and completing
• Vendor management, meaning your IT provider deals with Microsoft, your internet provider, and any other tech vendors on your behalf
• On-site support for issues that cannot be resolved remotely

What cheap IT support usually means

A provider quoting significantly below market rates is doing something differently. Sometimes that means they are newer to the business and trying to build a client base, which can work out fine. More often it means they are cutting corners somewhere.

Common corners that get cut: slower response times, less proactive monitoring, security that is reactive rather than preventive, and limited on-site availability. Some budget providers also lock clients into long contracts that are difficult to exit.

The real cost of cheap IT support shows up when something goes wrong and your provider is slow to respond, or when a security gap they never addressed leads to a breach.

Questions to ask any IT provider before signing

• What is your guaranteed response time for a critical issue, like a server that is down?
• Is on-site support included or billed extra?
• What security controls are included in the base price?
• Do you require a long-term contract?
• How many clients does each technician support? A high ratio means slower service.
• Can I speak with a current client in a similar business to mine?

A note on local vs. national providers

National IT support companies with call centers can handle a lot of things remotely. For a Chicago-area small business, local support matters when you need someone on-site. A national provider may sub out on-site work to a third party or charge a significant premium for it.

A local IT company knows the Chicago market, can be on-site quickly, and has a relationship with you rather than a ticket number. That relationship has real value when something goes wrong at a critical moment.