IT Services in Chicago
Everything your business needs from a Chicago IT partner. Managed IT, helpdesk, infrastructure, backup, project management, and strategic consulting — bundled or modular, sized to your team.
- ✓ 12 core IT services
- ✓ Bundle or pick & choose
- ✓ Chicago-based engineering
- ✓ 20+ years in Chicagoland
Get a Free IT Services Assessment
A 30-minute review of your environment and which IT services would have the highest impact.
One Provider for Every IT Service Your Business Needs
Most Chicago businesses end up with three or four IT vendors — one for helpdesk, one for cybersecurity, one for cloud, one for projects. We consolidate that into a single accountability point with one monthly invoice and one team that knows your environment end-to-end.
Browse All 12 IT Services
Each service is available as a standalone engagement or bundled into a comprehensive managed IT support agreement.
Managed IT Support
Comprehensive managed IT for Chicago businesses — 24/7 monitoring, helpdesk, patching, security, and vCIO strategy under one agreement.
Learn more →Helpdesk Support
Chicago-based helpdesk with response under one hour during business hours. Tier 1 to senior escalation, no offshoring.
Learn more →Onsite Support
Onsite engineering when something needs hands-on attention — hardware, network, server, or major incidents.
Learn more →Data Backup & Recovery
Automated backups for servers, workstations, and Microsoft 365, with quarterly tested restores and documented recovery objectives.
Learn more →IT Consulting & vCIO
Strategic technology guidance, roadmaps, and budgeting from a senior strategist on a fractional basis.
Learn more →Network Infrastructure
Network design, switching, Wi-Fi, VPN, and infrastructure management for Chicago offices and multi-site businesses.
Learn more →Remote Monitoring & Management
RMM for servers, workstations, and cloud services — most issues detected and resolved before users notice.
Learn more →IT Project Management
Server migrations, M365 deployments, Wi-Fi overhauls — scoped projects with fixed pricing and clear deliverables.
Learn more →Server & Workstation Management
Patching, hardening, monitoring, and lifecycle management for servers, desktops, and laptops across your fleet.
Learn more →VoIP Communications
Cloud-based VoIP phone systems for Chicago businesses — installation, configuration, and ongoing support.
Learn more →Web Development
Managed web development for Chicago businesses — design, build, and ongoing maintenance under one roof.
Learn more →Vendor Management
We manage your software licenses, ISP, telephony, and other vendor relationships so your team has one accountability point.
Learn more →One Hire vs. an Entire Bench.
Hiring a single in-house IT person costs roughly the same as a full Datastrive managed support agreement — but a single person can’t cover 24/7, can’t be a senior network engineer and a cybersecurity specialist and a vCIO at the same time, and goes on vacation. Managed IT support gives you depth, redundancy, and predictable cost without the recruiting risk.
- Compliance-Aware Engineering. CIS Controls, HIPAA, PCI DSS, and cyber insurance.
- Predictable Flat-Rate Pricing. One monthly invoice covers everything.
- Proactive, Not Reactive. Most issues resolved before your team notices.
- Local Chicago-Based Team. Onsite at your office, not on the other side of a phone tree.
Switching IT Providers Shouldn't Be Painful
Three steps to a calmer environment. Most onboardings are completed inside two weeks.
Schedule Your IT Health Check
A 30-minute call to understand your business, your software, and the IT pain points actually slowing you down.
Onsite Discovery
We visit your office to inventory your network, workstations, and security setup — everything we need to build an accurate proposal.
Tailored Proposal
You get a clear, fixed-price proposal mapped to your team size, your software, and your goals — no surprise add-ons.
Managed IT Support Across Chicagoland
Frequently Asked Questions
Common questions about IT services in Chicago and how Datastrive structures engagements.
What’s included in managed IT services?
Can I pick individual services or do I need to bundle?
How does pricing work for IT services?
Do you support Mac and Windows environments?
What size companies do you support?
Ready to Consolidate Your Chicago IT Vendors?
Book a free 30-minute IT assessment. We’ll review your current providers, identify which services overlap or have gaps, and quote a consolidated proposal — no obligation.
- ✓ 30-minute call with a senior engineer
- ✓ Vendor consolidation review
- ✓ Fixed-price proposal sized to your business
- ✓ Response within 1 business hour
Get a Free IT Services Assessment
A quick conversation about your IT vendors and where consolidation could help.