If you are planning a move to Microsoft 365, the first question is simple: what will it cost? The honest answer is that it depends, but it depends on a short list of things you can check yourself. Most providers in Chicago quote per mailbox, because email is the heart of the move and the easiest part to count.
This guide gives you typical ranges, shows what moves the price and lists the costs that get left off quotes. If you want help after the move, our Microsoft 365 support page explains what ongoing care looks like. The numbers below are typical ranges for small and mid-size offices, not promises.
A migration is a one-time project. The Microsoft license is a separate, monthly cost. Keep those two numbers apart when you compare quotes, or you will end up comparing things that are not the same.
What You Pay For in a Microsoft 365 Migration
A migration quote usually covers four things. Planning and inventory comes first: someone counts your mailboxes, shared mailboxes, file shares and devices. Then the data move itself, which copies email, calendars and contacts into your new tenant. Then setup, which covers security settings, user accounts and device connections. Last is cutover support, when your staff start using the new system.
Notice what is not on that list. The Microsoft 365 license is billed by Microsoft or your reseller each month. Training, phone changes and file server moves are often separate line items. A clean quote tells you what is in and what is out.
- Mailbox and calendar migration
- User and security setup
- Device and Outlook reconfiguration
- Cutover day support
- Short follow-up check after go-live
A good quote lists each part of the move so you can see exactly what the per-mailbox price includes.
Typical Per-Mailbox Pricing in Chicago
For a straightforward move, most Chicago providers charge roughly $40 to $150 per mailbox. The low end fits a small team moving from a simple hosted email service with little data. The high end fits older systems, large mailboxes or heavy customization. Many offices land in the middle.
Projects also carry a minimum. A five-person office often pays a flat project fee rather than a true per-mailbox rate, since planning and cutover take the same effort whether you have five users or fifteen.
| Office Size | Typical Project Range | Typical Timeline |
|---|---|---|
| 1 to 10 mailboxes | $800 to $2,500 | 1 to 2 weeks |
| 11 to 25 mailboxes | $2,000 to $5,000 | 2 to 3 weeks |
| 26 to 50 mailboxes | $4,000 to $9,000 | 3 to 5 weeks |
| 51 to 100 mailboxes | $8,000 to $18,000 | 4 to 8 weeks |
These are typical ranges, not quotes. Your real number depends on the factors in the next section.
What Pushes the Price Up or Down
Six factors do most of the work. Knowing them lets you predict whether your quote should be low or high before anyone visits.
- Data volume. A 5 GB mailbox moves in minutes. A 50 GB mailbox with years of attachments takes much longer.
- Source system. Moving from Google Workspace is usually simpler than from an old on-premises Exchange server.
- Shared mailboxes and rules. Each shared mailbox, distribution list and forwarding rule needs to be rebuilt by hand.
- Public folders and archives. Old archives and PST files add scanning and import time.
- Security setup. Multi-factor sign-in, device rules and email protection add setup hours, though they are worth it.
- Cutover timing. Weekend or after-hours work often costs more than weekday work.
An old on-site mail server can add several hours of cleanup that a cloud-to-cloud move never needs.
A Simple Mailbox Move vs. a Full Environment Move
Many offices only need email moved. Others want files, phones and devices to follow. The scope changes the price more than any other choice you make.
| Scope | What Moves | Cost Direction |
|---|---|---|
| Email only | Mailboxes, calendars, contacts | Lowest |
| Email plus files | Adds shared drives to OneDrive or SharePoint | Moderate |
| Full environment | Adds devices, security policies and phones | Highest |
| Phased move | Same scope, spread over weeks | Often similar total, easier cash flow |
If your files live on an old shared drive, ask about SharePoint consulting early. Setting up document libraries before the move costs less than reorganizing them afterward.
Costs That Get Left Off Quotes
The cheapest quote is not always the cheapest project. Several costs show up late when a provider scopes the work too narrowly.
- Microsoft licenses, billed monthly and separate from migration labor
- Backup of Microsoft 365 data, which Microsoft does not provide for you
- Replacing old PCs that cannot run current Outlook
- Third-party apps that connect to old email
- Staff training time and the productivity dip in week one
- Domain and DNS changes held by an outside registrar
Ask each provider to list what they excluded. A short exclusion list usually means a careful quote.
Week one after cutover is when most hidden costs, such as old PCs and missing training, surface.
How Providers Compare on Price and Scope
You have three common choices in Chicago. Each prices differently and covers different things.
| Ping Chicago | Freelance Consultant | Microsoft Reseller Only | |
|---|---|---|---|
| Pricing style | Fixed per-mailbox quote | Hourly, often open-ended | License sale, migration extra |
| Planning included | Yes, written scope | Varies | Usually minimal |
| After-hours cutover | Scheduled in the quote | Depends on availability | Often not offered |
| Ongoing support | Available after the move | Rarely | Limited |
| Backup & security setup | Offered in scope | Extra, if offered | Extra |
If you are weighing the project itself, our Microsoft 365 migration page shows how a typical move runs from start to finish.
How to Get a Fixed Quote You Can Trust
Gather five facts before you call anyone. Count your mailboxes, including shared ones. Note where your email lives today. Estimate total data size. List any apps tied to email. Decide what has to be ready on day one.
Then ask for a written, fixed price with a stated scope. If email is the only thing moving, email migration services may be all you need. A fixed quote protects you from surprise hours, and a short assessment call is usually enough to produce one.
Five facts, gathered in about thirty minutes, are enough for most providers to write a fixed quote.
The real cost of a Microsoft 365 migration is the mailbox price plus the pieces people forget: licenses, backup, old devices and training. Add those up before you compare quotes, and the differences between providers become much clearer.
A good next step is a short assessment. It counts your mailboxes, checks your current email and file setup and ends with a written, fixed price. You get a number you can plan around, with no pressure to commit.
FAQs
How much does a Microsoft 365 migration cost per mailbox in Chicago?
Most Chicago providers charge roughly $40 to $150 per mailbox for a standard move. Small offices often pay a flat project fee instead. Large mailboxes, old on-site servers and extra scope push the price toward the top of that range.
Is the Microsoft 365 license included in the migration price?
Usually not. Licenses are billed monthly by Microsoft or a reseller, separate from the one-time migration labor. When you compare quotes, confirm whether licensing, setup and support are listed as separate lines so the totals match.
How long does a migration take?
A team of 10 or fewer often finishes in one to two weeks. Larger offices with shared mailboxes and file moves can take four to eight weeks. Most of that time is planning and testing, not the actual data copy.
Will we lose email during the move?
A planned migration should not lose email. Mail keeps arriving during the move, and a final sync happens at cutover. Your provider should test with a few mailboxes first and keep your old system untouched until everything checks out.
Does Microsoft 365 back up my data?
Not in the way most owners expect. Microsoft keeps the service running, but you are responsible for your data. Separate backup is a common add-on, and it is worth pricing into your project from the start.
Why do some quotes come in much lower than others?
Cheap quotes often leave out planning, security setup, shared mailboxes or after-hours work. Ask what is excluded. A low number that grows through change orders costs more than a clear fixed price with a fuller scope.
Can we migrate over a weekend?
Yes, and many Chicago offices prefer it so staff start Monday on the new system. After-hours work can carry a premium, so ask whether the quote already includes it before you agree to a cutover date.
Do we need new computers to move to Microsoft 365?
Not usually. Most PCs from the last several years work fine. Very old machines or outdated Outlook versions may need replacing. A quick device inventory during planning will show which ones, if any, are a problem.
Reid Callahan
Editorial Director, Ping Chicago
Reid leads the Ping Chicago editorial team and works with our technicians to turn real support tickets, office moves and security reviews into plain-English guides for Chicago business owners. Born and raised in Chicago, he has spent more than 15 years in IT services, starting on the help desk and later running support and network projects for law firms, medical practices and manufacturers from the Loop to the western suburbs. He holds Microsoft 365 and CompTIA Security+ certifications and has helped hundreds of local offices move to the cloud. Today he focuses on how AI tools like Microsoft Copilot can save small teams time without putting company data at risk, and every guide he writes is checked by a working technician before it goes live.