Managed IT Services Pricing for Chicago Businesses (2026)
CIO Landing has one plan that covers all your day-to-day IT: support, monitoring, maintenance and the full security stack. It costs $150 to $225 per user per month, depending on how complex your environment is and how mature your technology is today. Projects are quoted separately.
Why we have only one plan
We don't strip out protections to hit a price point, and we won't leave a client exposed to save a few dollars. Every client gets the full security stack, and the price reflects your environment, not a menu of protections.
What moves you within the range
- Complexity: number of locations, servers, core business applications and compliance requirements.
- Maturity: how up to date your systems are. Outdated equipment and technical debt take more work to support. Take the technical debt self-assessment
Included for every user
- Help desk support for all of your users
- 24/7 device monitoring, security updates and patching
- Microsoft 365 or Google Workspace management
- Cybersecurity tools and monitoring: AI antivirus and managed detection and response (MDR), disk encryption, email protection and DMARC monitoring
- Security awareness training
- Backup and disaster recovery
- Employee onboarding and offboarding
- Client Success Manager and Technology Alignment Manager
- Technology Business Reviews and IT strategy
- Management of your other IT vendors
Full details are on our Service Levels page.
Estimate your monthly cost
$3,750–$5,625 per month
Users × $150–$225. Hardware, licenses and projects are extra.
Agreement terms
- Contract: 3-year agreement
- Onboarding: a one-time fee equal to one month of service
- All terms are public: read our Master Services Agreement, Service Level Objectives and other documents before you talk to us.
What costs extra
- Hardware, such as laptops, firewalls and Wi-Fi
- Software licenses, such as Microsoft 365 seats
- Projects, such as office moves and migrations, quoted up front (why we don't offer "unlimited projects")
- Fractional CIO (vCIO) strategy, such as a multi-year technology roadmap and IT budgeting, as an add-on (Fractional CIO services)
- After-hours work outside the plan, at the after-hours rates in your agreement
If we don't deliver, you can leave
A 3-year agreement only works if we earn it every month. If our service falls short, tell us in writing. We'll fix it, and if we can't, you can end the service. The details are in the "Service Warranty" section of our Master Services Agreement.
| What is happening | Response target |
|---|---|
| Everyone is down | 1 business hour |
| Many users or a critical system affected | 2 business hours |
| A few users affected, work continues | 4 business hours |
| One user, minor issue | 1 business day |
Example monthly costs
- 15-person nonprofit: $2,250–$3,375
- 25-person law firm: $3,750–$5,625
- 50-person manufacturer: $7,500–$11,250
Pricing questions
How much do managed IT services cost in Chicago?
At CIO Landing, managed IT costs $150 to $225 per user per month for all day-to-day IT. Projects are quoted separately. Where you land depends on the complexity and maturity of your environment.
Why is there only one plan?
Because every client gets the full security stack. Your price depends on the complexity and maturity of your environment, not on which protections you give up.
Do you offer unlimited projects?
No. Day-to-day support, monitoring, maintenance and security are all included in the monthly plan, but projects like migrations and office build-outs are quoted separately, in writing and up front, so you decide what happens and when. Here is why we work this way.
How long is the contract?
Three years, plus a one-time onboarding fee equal to one month of service. If our service falls short and we can't correct it, you can end the service under the warranty in our Master Services Agreement.
How fast do you respond?
Our targets are 1 business hour when everyone is down, 2 hours for critical systems, 4 hours when a few users are affected, and 1 business day for single-user issues.
Does the price change if we hire or downsize?
Yes. You pay per user, so the fee follows your headcount, with a minimum monthly fee set in the agreement.
Can I read your contract before a sales call?
Yes. All our agreements are published at ciolanding.com/documents.
Our IT provider was acquired and prices went up. What are our options?
See our MSP acquisitions tracker for what typically changes after a private equity buyout and how to switch. CIO Landing is independently owned.
