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Pick by where the work happens. Microsoft 365 Copilot fits companies whose work lives in Outlook, Teams, Word and SharePoint. ChatGPT Enterprise fits companies that want OpenAI models with data residency in ten regions. Claude, powered by Anthropic, fits teams doing long-document analysis, coding and agent work who want usage billed at API rates with admin spend limits. As of October 2026, only Copilot and Claude publish an enterprise price.
What does each one cost as of October 2026?
We opened each vendor's pricing page on October 26, 2026. The table lists what each page states. Where a vendor does not publish a number, we say so rather than repeat a figure from a reseller or a news story. Prices exclude tax and can change at any time, so recheck them before you build a budget.
| Plan | Published price | Terms that change the math |
|---|---|---|
| Claude Team | $20 per standard seat or $100 per premium seat per month, billed annually ($25 or $125 billed monthly) | 2 to 150 seats. Usage is included up to per-seat limits; usage credits at API rates are optional. |
| Claude Enterprise | $20 per seat per month, billed annually, plus all usage at API rates | 20-seat minimum on the self-serve plan. The seat fee covers access only; every token is billed on top. |
| ChatGPT Business | $20 per standard seat or $100 per premium seat per month, billed annually ($25 or $125 billed monthly) | For teams of 2 to 200. OpenAI says Business and Enterprise can buy credits for more access. |
| ChatGPT Enterprise | Not published. OpenAI lists custom pricing through sales. | OpenAI says credit-based and token-based pricing are available for Enterprise. |
| Microsoft 365 Copilot (enterprise add-on) | $30 per user per month paid yearly, or $31.50 paid monthly on an annual commitment | Requires a separate qualifying Microsoft 365 license. |
| Microsoft 365 Copilot Business (add-on) | $18 per user per month paid yearly, shown as reduced from $21 | For Microsoft 365 business plans. Microsoft notes usage-based billing for select advanced AI features. |
Do not compare the seat prices directly. The Claude Enterprise seat contains no usage at all, so its real cost is $240 per user per year plus whatever your people consume. The Copilot and ChatGPT Business seats bundle usage up to limits the vendor sets. A fair comparison models total annual cost for your actual mix of light users, daily users and engineers. Our Claude Enterprise cost guide, linked below, walks through that arithmetic.
How do the security and admin controls compare?
All three vendors say they do not train on business data by default, and all three offer single sign-on. The differences show up in identity provisioning, retention, where processing happens, and whether a Business Associate Agreement (BAA) is available for protected health information. The rows below come only from each vendor's own pages; a blank claim means we did not see it stated, not that the feature is missing.
| Control | Claude Enterprise | ChatGPT Enterprise | Microsoft 365 Copilot |
|---|---|---|---|
| Training on your content | None by default; Commercial Terms say Anthropic may not train on customer content | No training on business data by default | Microsoft says Copilot inherits your existing Microsoft 365 privacy and compliance policies |
| Identity provisioning | SSO, SCIM, domain capture, role-based access | SAML SSO, SCIM, domain verification, role-based access controls | Microsoft Entra accounts under your Microsoft 365 tenant |
| Audit and export | Audit logs and a Compliance API for chats, files and activity | Ask OpenAI which audit tooling your contract includes | Copilot Analytics and SharePoint Advanced Management are listed with the enterprise add-on |
| Retention | Custom retention, minimum 30 days | Custom data retention policies | Follows your Microsoft 365 policies, per Microsoft |
| Where processing happens | Data stored in the US; optional US-only inference at 1.1x usage rates | Data residency in US, EU, UK, Japan, Canada, South Korea, Singapore, India, Australia and UAE | Confirm region options with Microsoft for your tenant |
| Encryption keys | Customer-managed encryption keys | Enterprise Key Management | Confirm with Microsoft |
| Health data | HIPAA-ready offering with a click-to-accept BAA on Enterprise | Not stated on the pricing page; ask OpenAI | Not stated on the Copilot pricing pages; ask Microsoft |
Where does each assistant do its best work?
Microsoft 365 Copilot works inside Word, Excel, PowerPoint, Outlook, Teams and OneDrive, and grounds answers in your Microsoft Graph data: mail, files, meetings and chats. Copilot Chat is free for Entra users with an eligible Microsoft 365 subscription, and the paid license adds work-data grounding, prebuilt research and analysis agents, and custom agents from Copilot Studio. Microsoft says Copilot inherits your existing Microsoft 365 security, identity and compliance policies. That means it is only as well scoped as your sharing settings, and over-shared SharePoint sites are where most Copilot projects find trouble first.
ChatGPT Enterprise gives a standalone workspace with ChatGPT Work, Codex for coding, connectors to Google Workspace, Slack, GitHub and Microsoft 365, plugins, and an expanded context window. OpenAI lists a 128K-token window for its Instant models on Enterprise against 54K on Business, with 256K for its reasoning models on both. Companies already building on the OpenAI API often prefer it so prompts and tooling stay in one vendor.
Claude Enterprise puts chat, Claude Code and Cowork on one seat, so engineers and business users sit on the same contract and admin console. Anthropic lists context windows of up to 1M tokens, varying by model. That matters for contracts, policy manuals, data rooms and large code bases. Claude also runs inside Excel, Word, PowerPoint and Outlook through Claude for Microsoft 365. It connects to Google Drive, Gmail, Google Calendar, GitHub, Microsoft 365 and Slack, and admins can deploy Skills and plugins across the whole organization. For Salesforce shops, Claudeforce brings Salesforce into Claude and was in beta as of October 2026.
Which one should you pick?
| If this describes you | Start with | Why |
|---|---|---|
| Most work happens in Outlook, Teams and SharePoint, and you already pay for Microsoft 365 | Microsoft 365 Copilot | AI sits in the apps people open all day, grounded in Graph data, under your existing tenant controls. |
| You must process data in the EU, UK, Japan or another non-US region | ChatGPT Enterprise, or confirm options with Anthropic | OpenAI publishes ten residency regions; Anthropic states US storage. |
| Engineering and business teams need AI on one contract | Claude Enterprise | Claude Code and Cowork are included in the Enterprise seat, with usage metered per person. |
| You will put protected health information into chat | Claude Enterprise with HIPAA enabled, after legal review | Anthropic documents a self-serve BAA flow and lists exactly which features it covers. |
| Usage varies widely: a few heavy users, many light ones | Claude Enterprise | Light users cost little beyond the $20 seat, and limits can be set per user, per group or org-wide. |
| Under 150 people and you want a flat, predictable bill | Claude Team or ChatGPT Business | Both bundle usage into the seat at the same published seat prices. |
| Salesforce is your system of record | Compare Claudeforce and the Agentforce Sales app in ChatGPT | Both were in beta in 2026; see our guide to assistants with Salesforce. |
Can a company run more than one?
Yes. One workable pattern is Copilot for everyone in Microsoft 365, plus Claude or ChatGPT for analysts, engineers and the teams doing long-document work. The cost is real. You pay two sets of seats for the overlap group, you write one acceptable-use policy that covers both, and IT reviews two sets of connectors. Provision both through the same identity provider, and decide in writing which data classes each tool may touch. The setup that fails is letting each department buy its own tool on a credit card. That leaves you with three retention settings and no single audit trail.
What should you ask each vendor before you sign?
- What exactly is included in the seat price, and what is billed as usage, credits or add-ons?
- Which features are in beta, and does the contract cover beta features the same way?
- Where is our data stored, where is inference run, and can we restrict both in writing?
- Is a BAA available on the plan we are buying, and which features does it exclude?
- Can we set spend or usage limits by user and by group, and what happens when a limit is hit?
- How do we export chats and activity for legal hold, eDiscovery or audit?
- When a connector sends data to a third party, whose terms govern that data?
- What is the minimum seat count and term, and can seats be removed mid-term?
Where do these evaluations go wrong?
- Comparing seat prices only. A $20 Claude Enterprise seat and a $30 Copilot license measure different things.
- Piloting with enthusiasts. Ten power users will love any of the three tools. Include skeptical, light users so adoption numbers mean something.
- Skipping permissions cleanup. Every assistant that reads company files acts as the signed-in user. Fix over-shared folders and stale groups first.
- Assuming a BAA covers everything. The Anthropic BAA excludes data sent to third parties through connectors, and some beta features are unavailable on HIPAA-ready plans.
- No spend controls on day one. Agentic and coding surfaces use far more tokens than chat. Set group and user limits before go-live, not after the first invoice.
Questions people also ask
Is Claude Enterprise cheaper than Microsoft 365 Copilot?
The seat is cheaper: $20 per user per month for Claude Enterprise against $30 for the Copilot enterprise add-on, as of October 2026. But the Claude seat includes no usage, so total cost depends on how much your people use. Light users usually add little; engineers using Claude Code add much more.
Does ChatGPT Enterprise publish its price?
No. As of October 2026, OpenAI lists ChatGPT Enterprise as custom pricing through sales, with credit-based and token-based options. ChatGPT Business is published at $20 per standard seat per month billed annually.
Which of the three can sign a HIPAA BAA?
Anthropic documents a self-serve BAA for Claude Enterprise when the Primary Owner enables the HIPAA-ready offering. We did not see BAA terms on the ChatGPT or Copilot pricing pages, so ask OpenAI and Microsoft directly and get the answer in your contract.
Do any of them train on our company data?
Each vendor states that business data is not used for training by default. For Claude, the Anthropic Commercial Terms say Anthropic may not train models on customer content. Feedback that users submit with thumbs up or down is an exception, and admins can turn it off.
Can we use Claude inside Microsoft 365?
Yes. Anthropic lists Claude for Microsoft 365 and Claude for Microsoft Outlook on Team and Enterprise plans, with add-ins for Excel, Word, PowerPoint and Outlook. Usage there draws from the same organization spend limits as other Claude surfaces.
