IT Consulting · Chicago

IT Consulting in Chicago, IL

Chicago companies are moving offices, retiring servers and deciding what to do about AI, often in the same year. NetSys provides IT consulting for those decisions: written assessments, costed roadmaps, cloud and Microsoft 365 migrations, office move planning and a virtual CIO who keeps the plan current, delivered remotely by the engineers who carry it out.

The short answer

NetSys provides IT consulting in Chicago: assessments of your current environment, technology roadmaps with budget lines, Microsoft 365, SharePoint and Azure migrations, office relocation and network design, plans for replacing Windows Server 2016 and leftover Windows 10 machines, security and compliance programs, and virtual CIO reviews. Projects have fixed milestones, change windows in Central time, acceptance checks and a documented handover. The work is remote; NetSys does not send consultants on site in Chicago. A consulting project does not include an ongoing help desk unless you add a managed agreement, and fixed-price quotes follow a discovery call.

Service information by The NetSys Group. Our editorial standards.

How IT consulting works for Chicago projects

Consulting starts with discovery interviews over Teams, a read-only look at your Microsoft 365 tenant, firewall and servers through the access you grant, and an inventory script on each computer. From that we write the deliverable you hired us for, whether an assessment, a migration plan or a design, each with costs, risks and a timeline. Meetings and change windows are booked in Central time, and cutovers usually run on evenings or weekends so staff arrive to a working system. Because NetSys does not send consultants to Chicago, physical work is specified rather than performed: we write the cabling and rack plan, order equipment preconfigured and walk your contractor or building staff through installation on a video call. Every project ends with acceptance checks and handover documentation in IT Glue. Assessment, design and integration work is coordinated from Brooklyn, with meetings and change windows stated in Central time. The project has agreed milestones, acceptance checks and a handover. Ongoing monitoring and help desk require a separately defined managed scope.

Planning an office move in a shifting Chicago market

Downtown Chicago's office market is pushing firms to move. CBRE put direct vacancy in the central business district at 26.8% in the second quarter of 2026, with Class B space at 33.7% against 20.0% for Class A, and described larger tenants trading big footprints for smaller, better space; Fulton Market had the lowest vacancy, at 17.4%, and River North the highest, at 33.6%. Some vacated LaSalle Street buildings are becoming apartments, with the Bellwether Residences at 79 W. Monroe opening in September 2026. A move is an IT project with a fixed date. We confirm which carriers serve the new address and order circuits early, design Wi-Fi for the floor plan, size conference room systems, plan the network closet and schedule the cutover so the old lease does not end before the new circuit is live.

Servers, Windows deadlines and the move to the cloud

Windows 10 support ended on October 14, 2025, and Windows Server 2016 reaches the end of extended support on January 12, 2027, so many Chicago firms are planning both at once. The consulting question is what each server is still doing. File shares usually move to SharePoint and OneDrive, with a structure designed before any file is copied; line-of-business databases may move to Azure virtual machines, a vendor's hosted version or a newer server, depending on the vendor's support terms; identity moves to Entra ID so sign-in no longer depends on a box in the closet. We price each path, including licensing and the cost of staying put. Our published on-premises-to-Azure and OneDrive-to-SharePoint case study shows the method; it is not a Chicago engagement, but the steps would be the same.

Copilot, AI tools and Illinois's employment rule

Chicago leadership teams are asking whether Microsoft 365 Copilot or other AI tools are worth paying for, and whether their data is ready. Our readiness work checks SharePoint and Teams permissions first, because Copilot surfaces whatever a user can already open, then runs a pilot with a small group and measures the result before anyone buys licenses for the whole firm. Illinois adds a legal angle. Since January 1, 2026, amendments to the Illinois Human Rights Act made by HB 3773 bar employers from using AI that has the effect of discriminating against employees or applicants, including by using zip codes as a proxy, and require notice when AI is used for covered employment decisions. We inventory where AI tools touch recruiting, scheduling and performance reviews so your counsel can check them. This is general information, not legal advice.

How Chicago firms choose an IT consultant

Ask for written deliverables with numbers in them: an assessment report, a roadmap with budget lines by quarter, and a migration plan with acceptance checks. Ask who does the work after the presentation, because advice is cheaper to give when someone else has to implement it; at NetSys the engineer who writes the plan runs the project. Check that recommendations are vendor-neutral and that security is part of every design rather than a later add-on. After the project, a virtual CIO review each quarter keeps the roadmap, budget and risk register current, whether your own team, NetSys or another provider runs the day-to-day. For a Chicago firm with an internal IT manager, that review often becomes the place to settle priorities with the managing partner or the CFO.

What is included

IT Consulting in Chicago: what NetSys delivers

Know what you have

Discovery across every server, cloud tenant, device, circuit and contract, written up in IT Glue so it stays current
Risk register with the ten findings that matter most, each with a fix, an owner and a cost

Decide and build

Cloud strategy with real numbers: keep, refresh or migrate, for each workload, with Azure and Microsoft 365 sized from your data
Microsoft 365 architecture: Entra ID, Conditional Access, Intune, SharePoint information design and Exchange Online, in that order

Keep it honest

Virtual CIO reviews each quarter, with a written roadmap, a budget and a list of what changed
Vendor management for the decisions that involve a CRM, ERP, EHR or practice-management vendor

Published case study

On-prem servers to Azure and OneDrive to SharePoint

Two migrations in one engagement. The client's servers lived in the office, so the business lived with the office's power, cooling and hardware age, and years of files sat in individual OneDrive accounts shared ad hoc. NetSys assessed and sized each workload and moved it into Azure with identity anchored in Entra ID, designed a SharePoint structure of sites by function and permissions by role before moving a single file, migrated the OneDrive estate into it, set backups for both platforms and took on day-to-day management. The write-up is limited to the scope delivered, with no outcome figures claimed.

Read the full case study

From our client work

IT consulting work for other clients

Real estate
Commercial property management company
SharePoint migration of 800 GB of leases, vendor records, and property documents, with separate access permissions for 12 property teams.
SharePoint & OneDrive Migration IT for Real Estate and Property Management

Client names are withheld. These examples were chosen for the work involved, not for where the client is, so none is presented as a Chicago client.

What IT consulting costs in Chicago

Consulting is priced by the project or by the review rather than by the hour: an assessment has a fixed price based on the size of the environment, a migration is quoted from the workload inventory, and virtual CIO advisory is a monthly figure that scales with how many reviews and decisions a year you need. What moves the number is the number of systems and sites, the compliance standard in play and whether we are also managing the environment afterwards. Every quote is written from discovery, and the terms run month to month.

How the monthly fee is built

Who this fits, and who it does not

Best fit: 10 to 150 employees, a decision on the table that involves cloud, an office move, an acquisition, a compliance program or a system nobody trusts, and leadership that wants options with numbers rather than a sales deck.

IT Consulting in Chicago: FAQs

How does IT consulting work for Chicago organizations?

Remotely and in stages. Discovery interviews, environment reviews, design sessions and progress meetings happen over Teams in Central time, and project work runs through remote management tools and the Microsoft 365 and Azure admin centers. NetSys does not send consultants to Chicago. Anything physical, such as racking a firewall or moving desks, is written into a plan for your staff, landlord or contractor, with an engineer on a call while it happens. Each engagement has a written scope, a fixed price or quoted phases, milestones and a handover, and advisory work runs month to month.

What does IT consulting in Chicago cost?

We do not bill consulting by the hour or publish prices. An assessment carries a fixed price set by the size of the environment, migrations are quoted from an inventory of mailboxes, files, servers and applications, and virtual CIO advice is a monthly figure. The quote moves with the number of sites and systems, how much data is moving, the compliance standard involved, such as HIPAA or SEC rules, and how tight the deadline is, for example a lease end. Quotes are written after a discovery call, and nothing starts until you approve the scope.

What happens after the roadmap is delivered?

You choose who carries it out. Your own team can run it with the documentation we hand over; NetSys can run individual projects at quoted prices; or we can take over the environment under a managed IT agreement, with the roadmap as the plan. Whichever you pick, a quarterly virtual CIO review compares progress with the plan, updates the budget for the next four quarters and flags new risks, such as a server approaching the end of support or a contract renewal coming due, so the roadmap stays a working document rather than a binder.

How is IT consulting different from managed IT services?

Managed IT runs your environment every day: the help desk, monitoring, security, backups and vendors. Consulting answers a question or delivers a project with an end date, such as whether to move servers to Azure, how to prepare for an examination or audit, what a new office in Fulton Market needs, or what an acquisition target's IT will cost after closing. Many firms use both, with consulting decisions feeding the managed roadmap. Others hire us only for a project and keep their current support provider; we hand over clean documentation either way.

Can you review an acquisition target's IT before we close?

Yes. For a Chicago buyer or private equity sponsor, we review the target's Microsoft 365 tenant, devices, servers, backups, security controls, licensing and contracts within the access the deal allows, and report the risks and the cost of bringing the company up to your standard. Typical findings are unsupported servers, missing multifactor sign-in, backups that have never been restored and software licenses that do not transfer. The report separates items to fix before closing from first-year work, so the numbers can go into the purchase agreement or the integration budget.

Engineers, not a sales deck

Bring the decision you are stuck on.

A cloud move, a merger, a compliance deadline, a system nobody trusts. Tell us what you run and what has to change, and an engineer comes back with an assessment, options with real numbers and the order to do them in.

Explore IT Consulting Scope 845-203-3914