Almost every small business in the Chicagoland area faces this decision at some point: Microsoft 365 or Google Workspace? Sometimes it comes up when you're starting fresh and need to set up business email. Sometimes it comes up when a team is frustrated with their current setup and wants to switch. Sometimes it comes up when a business gets acquired or merges with another company and suddenly has people on both platforms trying to collaborate.
Both products are mature, capable, and used by millions of businesses. Both will handle your email, documents, file storage, video calls, and team communication. Neither is dramatically better than the other in an absolute sense. But they're built with different assumptions about how people work, and for a given business at a given stage, one is almost always the smarter choice.
This post gives you a practical framework for making that call — without the marketing language from either vendor.
What You're Actually Choosing Between
Microsoft 365 (formerly Office 365) is built around desktop applications. Word, Excel, PowerPoint, Outlook — these are the core. The cloud layer (OneDrive, SharePoint, Teams) was added on top of a decades-old desktop software foundation, and it shows. Microsoft 365 is powerful, deeply integrated with Windows, and extremely capable for complex documents and spreadsheets. It's also more complex to administer and has a steeper learning curve for users who aren't already familiar with the Microsoft ecosystem.
Google Workspace (formerly G Suite) is built browser-first. Gmail, Google Docs, Sheets, Drive, and Meet were designed to run in a tab, not as installed software. Real-time collaboration — multiple people editing the same document simultaneously without file conflicts — is native to the platform rather than bolted on. Administration is significantly simpler, and the learning curve is lower for users who spend most of their day in a browser. The tradeoff is that Google's apps are less powerful for complex formatting, advanced spreadsheet work, and document-heavy workflows.
The choice often isn't about which platform is objectively better — it's about which one fits how your team actually works.
Pricing: Closer Than You Think
Both platforms have tiered pricing, and at comparable feature levels, they're within a few dollars per user per month of each other.
Microsoft 365 Business Basic runs about $6 per user per month and includes web and mobile apps, Teams, Exchange email, and 1TB of OneDrive storage. Microsoft 365 Business Standard is roughly $12.50 per user per month and adds desktop installations of the full Office suite — Word, Excel, PowerPoint, and Outlook on up to five devices per user. Microsoft 365 Business Premium, at around $22 per user per month, adds advanced security and compliance features relevant to businesses in regulated industries.
Google Workspace Business Starter runs about $7 per user per month with 30GB of pooled Drive storage and the standard app suite. Business Standard is around $14 per user per month with 2TB of pooled storage and enhanced video meeting features. Business Plus, at about $22 per user per month, adds enhanced audit and compliance tools.
For a 20-person Chicagoland business, the mid-tier plans land you in the $280 to $440 per month range on either platform — a difference of $20 to $40 per month that's unlikely to drive the decision. Where cost differences become meaningful is in migration and transition: switching platforms costs real time and money, and that cost often dwarfs a year or two of subscription differences.
Where Microsoft 365 Has a Clear Edge
Microsoft 365 is the stronger choice in several specific scenarios that are common among Chicagoland SMBs.
If your business depends on complex Excel spreadsheets — financial models, operational data analysis, pivot tables, advanced formulas — Microsoft Excel is meaningfully more powerful than Google Sheets. This matters most for professional services firms, financial advisors, operations-heavy businesses, and anyone whose core workflows live in spreadsheets that go beyond basic data entry and reporting.
If your team produces documents that need precise formatting — contracts, proposals, reports with complex headers and footers, documents that clients and partners will print — Word gives you more control than Google Docs. Google Docs has improved substantially, but the rendering differences between platforms and the formatting inconsistencies when converting between file types are real issues for document-intensive businesses.
If you're in a regulated industry — healthcare, financial services, legal, government contracting — Microsoft 365's compliance and security toolset is more mature. Features like advanced eDiscovery, data loss prevention, Azure Active Directory integration, and Microsoft Purview are enterprise-grade and have been battle-tested in highly regulated environments. Google Workspace has added compliance features, but Microsoft has a longer track record and more depth here.
If your team is already on Windows and familiar with the Office suite, the friction of switching is real. People know where things are. Existing macros, templates, and custom formatting work. The learning curve for your IT administrator is lower. When the incumbent platform serves the business well, there's often no compelling reason to switch.
Where Google Workspace Has a Clear Edge
Google Workspace wins in its own set of scenarios that are equally common among the businesses we work with.
If real-time collaboration is central to how your team works — multiple people writing and editing documents simultaneously, commenting and resolving feedback in context, working from different devices without worrying about which version is current — Google Workspace is simply better. The collaboration model is native rather than added on, and it shows. Microsoft has made significant improvements to real-time co-editing in recent years, but Google still has the smoother experience for teams that spend their day collaborating on documents.
If you're a younger business without legacy Microsoft file dependencies, Google Workspace is easier to set up and administer. The admin console is straightforward, user management is intuitive, and you don't need an IT specialist to add users, reset passwords, or manage basic configuration. For a 10-person team where nobody has a dedicated IT background, that operational simplicity has real value.
If your team is distributed or remote, Google Workspace tends to feel more cohesive as a browser-based platform. Everything works regardless of operating system — Windows, Mac, Chromebook, Linux — without desktop software installation or licensing concerns. This matters for businesses with employees on different devices or contractors who need access without IT provisioning a machine.
If you're integrating with a lot of modern SaaS tools, both platforms have extensive integrations, but Google Workspace tends to have slightly simpler OAuth connections and is favored by a lot of newer SaaS products as the default integration target. This isn't a decisive factor, but it's worth noting if your business runs on a stack of cloud tools.
The Migration Question
Switching platforms is the part of this decision that most businesses underestimate. Email migration is the easy part — moving mailboxes from one platform to another is well-documented and tool-supported. For a 20-person business, an experienced IT team can complete the email cutover in a weekend with minimal disruption.
The harder part is everything else. Documents stored in Google Drive don't convert cleanly to Microsoft format, and vice versa. Formatting drifts. Formulas behave differently. Any macros or scripts written in Google Apps Script don't work in Microsoft 365, and VBA macros don't work in Google Sheets. If your team has built workflows, templates, or automations on one platform, those need to be rebuilt on the other — and that work is often invisible until someone tries to do it.
Calendar integrations with third-party tools, CRM connections, scheduling software, and any apps that are tightly coupled to one platform need to be re-evaluated. Some will work with both; others are built around one ecosystem and will require alternative tools or custom integration work.
For a typical Chicagoland small business with 10 to 50 employees making a full platform switch, realistic planning should account for two to four weeks of transition time — including a parallel running period, user training, and a tail of resolving edge cases after cutover. Factor this into the decision honestly, because a migration that's poorly planned is one of the fastest ways to disrupt a team's productivity at exactly the wrong moment.
A Framework for Making the Call
Rather than a generic checklist, here are the three questions that most reliably point to the right answer for businesses we work with in the Chicago area.
What does your team use most? If your employees spend most of their day in Word, Excel, and Outlook and know the keyboard shortcuts by heart, switching to Google Workspace creates friction that shows up in lost productivity for months. If your team already lives in a browser and treats email as just one of many communication tools, Google Workspace feels natural and Microsoft 365 will feel clunky. Respect where your team is already comfortable.
What's your most complex document or spreadsheet workflow? Pull up the three most important documents or spreadsheets in your business — the ones you couldn't function without. Open them in the other platform and see what breaks. This is the fastest way to discover whether a migration is straightforward or a significant project. If everything looks fine, the switch is lower-risk. If formulas break, formatting shifts, or macros stop working, you have a clear signal of what migration effort looks like in practice.
Where is your IT complexity headed? A 15-person consulting firm with straightforward workflows and modern tooling is a very different environment from a 60-person logistics company with compliance requirements, custom software integrations, and a mixed Windows/Mac environment. The simpler the IT environment, the more Google Workspace's operational simplicity matters. As complexity grows, Microsoft 365's broader enterprise feature set starts to justify the added administrative overhead.
The Decision Most Businesses Avoid
What we see most often isn't a business that has made a deliberate choice between the two platforms — it's a business that's drifted into a mix of both without ever deciding. Some employees use Outlook, some use Gmail. Files live in both Drive and OneDrive. Documents get converted back and forth and gradually accumulate formatting issues. No one is quite sure where the authoritative version of a file lives.
This is more common among businesses in the 20 to 75 employee range that grew organically without standardizing early. The cost isn't visible on any invoice, but it's real: time wasted on file versioning confusion, collaboration friction between teams on different platforms, and the overhead of administering two environments instead of one.
If this sounds like your situation, the best version of this decision isn't "Microsoft 365 or Google Workspace" — it's "how do we get everyone on the same platform and actually stay there." That's a project worth planning properly, with the right support, rather than something to tackle over a few weekends.
If you'd like a practical assessment of which platform fits your current environment and what a migration would actually involve, that's exactly the kind of evaluation we do for businesses across Chicagoland. Reach out and we'll give you a straight answer.