Managed IT Services for Chicago, IL Businesses
IT LEGENDS LLC provides security-first, modern IT support for Chicago solo professionals, professional firms, clinics, and small & medium businesses that depend on reliable technology.
Whether you’re downtown in the Loop, on the North Side, or running a distributed team, we help you standardize devices, secure Microsoft 365, and respond quickly when something breaks — without enterprise complexity or long-term contracts.
What We Do for Chicago Teams
We keep Chicago offices, clinics, and solo pros stable, secure, and supported — so your staff can stay focused on clients instead of IT issues.
Managed Devices
- Standardized builds for workstations & laptops
- Health monitoring, patching & remote tools
- Onboarding/offboarding support for new hires
Microsoft 365 & Collaboration
- Tenant setup and ongoing administration
- MFA, security policies & basic conditional access
- Teams, Exchange, OneDrive and SharePoint basics
Security & Resilience
- Endpoint protection (AV/EDR) deployment
- Backup strategy & basic recovery testing
- Network & Wi-Fi review and recommendations
Right-Sized Bundles for Chicago
Our core bundles fit solo professionals, small firms, and regulated offices across the Chicago area. Start small and evolve over time.
Home & Solo Bundle
For Chicago solo pros & home offices.
Starts at $109/month (up to 3 devices)
- Managed laptops/desktops
- Core security & remote support
- Ideal for consultants, agents & independent professionals
Business Essentials
For offices & growing teams in Chicago.
Starts at $189/month (up to 5 users)
- Managed workstations & core servers
- Microsoft 365 tenant management
- Network monitoring & backup basics
Industry Plus
For clinics & regulated Chicago offices.
Starts at $289/month (up to 10 users)
- Stronger security policies & MFA guidance
- Vendor coordination (EHR, accounting, line-of-business apps)
- Quarterly IT & security reviews
Why Chicago Businesses Work with IT LEGENDS
You don’t need a huge IT department — you need a partner that answers quickly, speaks clearly, and helps you make smart decisions over time.
Security-First, Business-Friendly
- Security-first mindset without scare tactics
- Plain-language explanations & clear options
- Roadmap thinking instead of one-time fixes
Flexible, No Long-Term Contracts
- No long-term lock-in for Chicago clients
- Bundles that grow with your team
- Founder-led service and fast response times
Ready to Talk About Chicago IT Support?
Start with our short consultation form. Tell us how many users/devices you have and what’s not working today. You’ll then be redirected to our calendar to pick a consultation time.
Start Consultation Form & Pick a Time