Chicago's Small Business Tech Experts
360° Technology Coverage
We love technology and we love helping businesses succeed. From Managed IT Services to Cybersecurity, we've got you covered.

Managed IT Services
Eliminate your tech debt with expert IT Managed Services. We handle your technology needs so you can focus on growth—offering unlimited support, proactive maintenance, and scalable solutions. Trust us to keep your systems running smoothly.

Cybersecurity
We provide 24/7 threat monitoring, proactive defense strategies, and elegant solutions tailored to protect your data and systems. We ensure your business stays secure with our robust security measures, compliance support, and real-time threat detection.

Mobile Devices
Keep your focus on delivering exceptional customer experiences while we handle the technical aspects of your tablet-based operations. Trust us to optimize efficiency and security in your storefront with our specialized mobile device management solutions.

System Integrations
We provide customized solutions to seamlessly connect diverse systems and technologies, ensuring a unified and efficient operational environment. Once integrated, automations and AI agents can be tailored to your needs.

Security Training
Empower your team with essential cybersecurity knowledge and threat awareness through tailored training solutions. Assess your preparedness with simulated phising attacks and social engineering campaigns.

Backup & Compliance
Ensure your data is safe and operations compliant with our robust backup and documentation solution. Offsite backups and auditable documentation designed for PCI, SOC2, and other compliance needs.
Instant Savings Estimate
Use the form below to get a savings estimate based on your specific IT needs.
YOUR TECHNOLOGY PARTNER
Hey! 👋 I'm Brennan Walls
I spent the last half-decade building and managing the IT department for a seven-figure manufacturing company. I founded Windy City Cyber because I know there are other SMBs, Teams, and Entrepreneurs who need help to bridge the gap between what they want from their tech and their budget.
Passionate About SMB
I enjoy how rewarding it is to work with smaller firms and companies who have fallen "out of love" with their technology and need a fresh perspective.
A Maker at Heart
All my life I've wanted to build things and solve problems, so that's what I've gotten good at: innovative, cost-effective, and elegant solutions coupled with hard work.