Microsoft 365 Migration Services for Chicago Businesses
A Microsoft 365 migration touches every person in your business at once. Email, calendars, shared files and the way people work together all change on the same day, which is why the planning matters more than the tools.
Datastrive plans and runs Microsoft 365 and Office 365 migrations for Chicago businesses moving from on-premises Exchange, Google Workspace, another Microsoft 365 tenant, or a file server to SharePoint and OneDrive. We map what you have, agree the plan with you, and support your team through the first days after the switch.
- Based in Chicago, serving businesses across Cook, DuPage, Lake and Will counties
- Discovery and a written cutover plan before anything moves
- Pilot group first, then the rest of the business
- Handed over to ongoing Microsoft 365 management if you want us to keep looking after it
Schedule a Microsoft 365 Migration Review
Tell us a little about your business and someone from our team will reach out to set up a time. Your information stays private.
The Migration Is a Day. The Planning Is the Project.
Mailboxes are usually the easy part. The surprises come from everything around them: shared mailboxes nobody mentioned, a scanner that emails to an old server, calendar permissions an assistant relies on, DNS records that need to change at the right moment, and phones that need setting up again.
We find those things before cutover, not after.
A good migration ends with your team checking their email on Monday and wondering what changed.
What Usually Goes Wrong in a Microsoft 365 Migration
These are the details that turn a straightforward migration into a difficult week, and the ones we plan for first.
Shared Mailboxes and Permissions Missed
Delegated calendars, shared inboxes and send-as permissions are easy to overlook and immediately noticed when they’re gone.
Devices and Phones Left Behind
Outlook profiles, phones and tablets need reconnecting after the move. Without a plan, the first morning becomes a queue of people who can’t get their email.
Files Moved Without Structure
Copying a messy file server into SharePoint gives you a messy SharePoint. Migration is the best chance to fix structure and permissions.
Security Configured Later, or Never
A new tenant should have multi-factor authentication, admin roles and sharing settings in place before users arrive, not added once something goes wrong.
Mail Flow Changed at the Wrong Time
DNS and mail routing changes need to line up with the cutover. Get the timing wrong and email bounces or lands in the old system while everyone assumes it moved.
What Our Microsoft 365 Migration Covers
Exchange to Microsoft 365
Mailboxes, calendars, contacts, shared mailboxes and public folders moved from on-premises Exchange, with DNS and mail flow changes timed to cutover.
Google Workspace to Microsoft 365
Gmail, Calendar, Contacts and Google Drive content moved across, with help for your team adjusting to Outlook, Teams and OneDrive.
Tenant-to-Tenant Migration
For mergers, acquisitions, rebrands or untangling a tenant someone else set up, we move users, mailboxes and files between Microsoft 365 tenants.
Security Built Around a Recognized Framework
The new tenant is configured around the CIS Controls v8.1 framework before users arrive: multi-factor authentication, admin roles, sharing settings and alerting. See our cybersecurity services for the wider security catalog.
File Server to SharePoint and OneDrive
Shared drives restructured into SharePoint sites and Teams, personal files moved to OneDrive, and permissions cleaned up along the way. For moves beyond Microsoft 365, see cloud migration.
Licensing and Post-Migration Support
The right licenses chosen before the move, then help reconnecting devices, answering questions and fixing anything that didn’t behave as planned in the days after cutover.
How a Microsoft 365 Migration Works With Datastrive
Every Microsoft 365 migration follows the same order, whatever you’re moving from.
We’ll be honest about any short windows where something is limited during cutover, rather than promising none at all.
Migration Project or Ongoing Management?
You can hire us for either. Most businesses keep the team that ran their migration because we already know the environment. See Microsoft 365 management and IT project management for how we scope each.
Microsoft 365 Migration Across Chicago Industries
Law firms need document permissions and mailbox retention carried across carefully. Healthcare practices need access to patient-related information handled from day one. Financial services firms need retention settings that match their obligations. Non-profits often qualify for discounted licensing that should be in place before the move.
We plan the migration around the way your sector works.
See our industries page for the full list, including legal, healthcare, financial services, manufacturing and nonprofits.
Microsoft 365 Migration Across Chicago and the Suburbs
Planning and migration work happen mostly remotely, with onsite support for discovery and the first morning after cutover when it helps. We work with businesses throughout Chicago and the surrounding area, including Skokie, Schaumburg, Naperville, Oak Brook, Elk Grove Village, Rosemont, Downers Grove and Aurora. Full coverage details are on our Chicagoland service area page.
Getting Started With Datastrive
A conversation about what you’re moving from.
Exchange, Google Workspace, another tenant or a file server: you tell us what you have and how many people it affects.
A review of your environment.
We look at mailboxes, files, devices and DNS and flag anything that could cause trouble on cutover day.
A written migration plan.
You get a scoped plan with timing, responsibilities and cost. No obligation and no pitch for licenses you don’t need.
Frequently Asked Questions About Microsoft 365 Migration in Chicago
How long does a Microsoft 365 migration take?
Will we lose email during the migration?
Can you migrate us from Google Workspace to Microsoft 365?
What is the difference between Office 365 and Microsoft 365 migration?
Do we need to change our licenses before migrating?
What happens to our old server after the migration?
How do existing clients get help during a migration?
Moving to Microsoft 365? Start With a Plan.
Tell us what you’re moving from and how many people it affects. We’ll explain what the migration would involve, how we’d schedule it and what it would cost.
Schedule a Microsoft 365 Migration Review
Tell us a little about your business and someone from our team will reach out to set up a time. Your information stays private.