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Home › Categories › AI Assistants

AI Assistants for Teams, Compared: Verified 2026 Pricing

Bill BelcaminoBy Bill Belcamino · Last updated September 27, 2026 · Our methodologyResearched and fact-checked by the HelpCompare team

Side-by-side pricing for ChatGPT, Claude, Gemini, Microsoft 365 Copilot and Perplexity: entry price, free plan, how each vendor bills for AI, and the date we last checked each figure against the vendor’s own pricing page.

AI Assistants for Teams, ComparedVerified Sep 27, 2026
Bill Belcamino
Bottom line up frontby Bill Belcamino, founder of HelpCompare
Editorial assessment

Bottom line up front: Which AI assistant is worth paying for at work?

Pay for the one that puts company data under your admin's control, because staff are probably using free personal accounts already.

Gemini comes with Google Workspace from $7/user/mo and Copilot Chat is included with eligible Microsoft 365 business plans, while ChatGPT Business and Claude Team both start from $20/seat/mo on annual billing with a 2-seat minimum. The page's sharpest detail is on Gemini: Workspace-licensed chats aren't human-reviewed or used to train models, and personal Google accounts don't get that protection. So the business seat is really a data policy you can enforce, and it only works if you also name the approved tool and say what must never be pasted in. Don't license everyone on day one. Usage is lopsided, so seat the people already using AI every week, check actual use after a month, and expect plans, prices and limits here to change often.

Verified data · quick answer
  • Lowest published entry price: Gemini — Included in Google Workspace from $7/user/mo (annual).
  • Free plans: ChatGPT (Free plan for individuals); Claude (Free plan for individuals); Gemini (Free Gemini app for personal Google Accounts; business use via Workspace); Microsoft 365 Copilot (Copilot Chat included with eligible Microsoft 365 business plans); Perplexity (Yes: search with citations and basic models).

My read of the verified data on this page, checked against vendor sources on September 27, 2026. Disagree or spot an error? Tell Bill

Heads up: AI assistants change their plans, prices, models and usage limits almost daily. Every figure on this page is accurate as of the date shown next to it, the date we checked the vendor’s own pricing page. Confirm current terms on the vendor’s site before you buy.

Most-read in this category: Claude vs Microsoft 365 Copilot · Claude vs Gemini · ChatGPT to Microsoft 365 Copilot

AI Assistants pricing at a glance

Every row links to the comparison where the figure was verified and to the vendor’s pricing page.

ToolEntry priceFree planAI billingG2 ratingVerifiedSource
ChatGPTFree plan; Business from $20/seat/mo (annual, 2-seat min)Yes — Free plan for individuals——September 19, 2026in ChatGPT vs ClaudeVendor pricing ↗
ClaudeFree plan; Team from $20/seat/mo (annual, 2-seat min)Yes — Free plan for individuals——September 19, 2026in ChatGPT vs ClaudeVendor pricing ↗
GeminiIncluded in Google Workspace from $7/user/mo (annual)Free Gemini app for personal Google Accounts; business use via Workspace——September 19, 2026in ChatGPT vs GeminiVendor pricing ↗
Microsoft 365 CopilotCopilot Chat free with Microsoft 365; Copilot Business $18/user/mo add-on (annual, discounted from $21 through Dec 31, 2026)Copilot Chat included with eligible Microsoft 365 business plans—4.4 / 5431 reviewsSeptember 23, 2026in ChatGPT vs Microsoft 365 CopilotVendor pricing ↗
PerplexityFree plan; Pro $20/mo or $17/mo billed annually; Enterprise Pro $40/seat/mo or $400/seat/yrYes: search with citations and basic models——September 27, 2026in Perplexity vs ChatGPTVendor pricing ↗

Head-to-head comparisons

ChatGPT vs ClaudeUpdated September 19, 2026ChatGPT vs GeminiUpdated September 19, 2026ChatGPT vs Microsoft 365 CopilotUpdated September 19, 2026Claude vs GeminiUpdated September 23, 2026Claude vs Microsoft 365 CopilotUpdated September 23, 2026Perplexity vs ChatGPTUpdated September 27, 2026

Switching guides

ChatGPT to ClaudeSwitching guideChatGPT to GeminiSwitching guideChatGPT to Microsoft 365 CopilotSwitching guideChatGPT to PerplexitySwitching guideClaude to ChatGPTSwitching guideClaude to GeminiSwitching guideClaude to Microsoft 365 CopilotSwitching guideGemini to ChatGPTSwitching guideGemini to ClaudeSwitching guideMicrosoft 365 Copilot to ChatGPTSwitching guideMicrosoft 365 Copilot to ClaudeSwitching guidePerplexity to ChatGPTSwitching guide
Verified data

AI Assistants: security, offline & remote work

The AI assistant tools we track, side by side on compliance, single sign-on, offline access and remote or office controls. Every value links to the vendor page it came from.

What we checkedChatGPTClaudeGeminiMicrosoft 365 CopilotPerplexity
Security & compliance
SOC 2 reportSOC 2 Type IIsourceSOC 2 Type IIsourceNot publishedNot publishedSOC 2 Type IIsource
ISO/IEC 27001CertifiedsourceCertifiedsourceCertifiedsourceCertifiedsourceNot published
Other certificationsISO/IEC 27017, ISO/IEC 27018, ISO/IEC 27701, ISO/IEC 42001, SOC 3, PCI DSS v4.0.1, CSA STAR, FedRAMP 20x, TX-RAMPsourceISO/IEC 42001, HIPAAsourceSOC 1, SOC 3, ISO 9001, ISO/IEC 27701, ISO/IEC 27017, ISO/IEC 27018, ISO/IEC 42001, FedRAMP High, BSI C5sourceISO/IEC 42001sourceNot published
HIPAA (BAA)BAA availableEnterprisesourceBAA availableEnterprisesourceBAA availablesourceBAA availablesourceNot published
GDPR data processing agreementDPA offeredsourceDPA offeredsourceDPA offeredsourceDPA offeredsourceDPA offeredsource
Single sign-on (SAML/OIDC)YesBusinesssourceYesTeamsourceYesBusiness StartersourceYesAny eligible Microsoft 365 plan (sign-in via Microsoft Entra ID)sourceYesEnterprise Prosource
SCIM user provisioningYesEnterprisesourceYesEnterprisesourceNot publishedNot publishedYesEnterprise (org-wide once the org has an Enterprise Max seat)source
Two-factor authenticationYessourceNot publishedYesEnforcement: Business StartersourceYesEnforcement: All Microsoft 365 plans via Entra ID security defaults; Conditional Access policies need Entra ID P1 (included in Business Premium)sourceNot published
Admin audit logYesEnterprisesourceYesEnterprisesourceYesBusiness StartersourceYesCopilot Chat (included)sourceYesEnterprise (org-wide once the org has an Enterprise Max seat)source
Data residency choicesUS, EU, UK, Japan, Canada, South Korea, Singapore, India, Australia, UAEEnterprisesourceUS onlysourceUS, EUBusiness StandardsourceNot publishedNot published
EncryptionAES-256 at rest; TLS 1.2+ in transitsourceEncrypted in transit and at rest; customer-managed encryption keys (AWS KMS, Google Cloud KMS, Azure Key Vault) for eligible Enterprise organizationssourceAES-256 at rest and in transit (Drive/Docs files); client-side encryption available on Enterprise PlussourceBitLocker and per-file encryption at rest; TLS and IPsec in transitsourceEnd-to-end encryption (stated)source
Self-hosting optionNot publishedNot publishedNot publishedNot publishedNot published
Offline access
Offline modeNot documentedNeeds a connectionAnthropic states Cowork needs an active internet connection throughout a session; no offline mode is documented for Claude chat on any app.sourceNeeds a connectionGemini's desktop apps require an internet connection to use Gemini's features; no offline mode is documented.sourceNot documentedNot documented
Desktop appsWindows, macOSsourceWindows, macOS, LinuxsourceWindows, macOSsourceWindows, macOSsourceNot published
Mobile appsiOS, AndroidsourceiOS, AndroidsourceiOS, AndroidsourceiOS, AndroidsourceNot published
Remote, hybrid & in-office
IP allowlistingYesEnterprisesourceYesEnterprisesourceYesEnterprisesourceYesMicrosoft 365 Business Premium (Entra ID P1 Conditional Access)sourceNot published
Device & session controlsYesEnterpriseEnterprise: Intune for iOS (pricing table) and Workspace Blocking via a ChatGPT-Allowed-Workspace-Id HTTP header on the corporate network; not ticked for Business.sourceYesEnterpriseEnterprise admins can shorten session length (1, 7, 14 or 28 days); Team and Enterprise get enterprise deployment for the desktop app and admin controls for remote and local connectors.sourceYesBusiness StarterFundamental endpoint management on all Business editions: remote account sign-out, block devices, basic mobile device management, endpoint verification; advanced mobile management and remote device wipe on Business Plus; Context-Aware Access on Enterprise.sourceNot publishedNot published
Office & room hardware———Copilot in Teams Phone works on VoIP and PSTN calls; no Copilot-specific room hardware is documented.source—
Editorial assessment

What this means for your team

  • Audit reports: ChatGPT, Claude and Perplexity state a SOC 2 report on their own site; we found no SOC 2 statement for Gemini and Microsoft 365 Copilot. If your security team requires SOC 2, ask Gemini and Microsoft 365 Copilot directly before shortlisting.
  • Single sign-on: ChatGPT includes it on Business; Claude includes it on Team; Gemini includes it on Business Starter; Microsoft 365 Copilot includes it on Any eligible Microsoft 365 plan (sign-in via Microsoft Entra ID); Perplexity includes it on Enterprise Pro. If your team signs in through Okta, Microsoft Entra ID or Google, price the ChatGPT, Claude and Perplexity plans that include SSO, not their entry plans; Gemini and Microsoft 365 Copilot include it on the entry plan.
  • Health data: ChatGPT, Claude, Gemini and Microsoft 365 Copilot will sign a HIPAA business associate agreement (ChatGPT: Enterprise; Claude: Enterprise). We found no BAA offer for Perplexity, so keep protected health information out of it.
  • Working offline: Claude and Gemini need an internet connection; ChatGPT, Microsoft 365 Copilot and Perplexity don’t document an offline mode. Details are in the Offline mode row above.
  • Office-only access: ChatGPT can restrict sign-ins to approved IP ranges on Enterprise; Claude can restrict sign-ins to approved IP ranges on Enterprise; Gemini can restrict sign-ins to approved IP ranges on Enterprise; Microsoft 365 Copilot can restrict sign-ins to approved IP ranges on Microsoft 365 Business Premium (Entra ID P1 Conditional Access). That suits an office network or a company VPN; fully remote teams need a VPN for it to work.
  • Where your data lives: ChatGPT lets you choose US, EU, UK, Japan, Canada, South Korea, Singapore, India, Australia, UAE on Enterprise; Gemini lets you choose US, EU on Business Standard. This matters for teams hiring across the EU, UK or Australia.
  • In the office: Microsoft 365 Copilot: Copilot in Teams Phone works on VoIP and PSTN calls; no Copilot-specific room hardware is documented.

ChatGPT: worth knowing

  • SecurityBusiness data residency is rolling out gradually; if a non-US region is chosen, a copy of every prompt and response is still stored in the US for a limited time for abuse monitoring. source
  • RemoteIn Business workspaces admins can view, access, export and delete member conversations, though by default they cannot see all private member chats in the product. source
  • RemoteSelf-serve Business can't pay by invoice, PO, ACH or wire; organisations needing those must buy a contracted plan such as Enterprise. source

Claude: worth knowing

  • RemoteOn Enterprise, admins can restrict access to approved CIDR ranges such as office locations and VPN exit points; requests from other IPs are blocked. source
  • SecurityCustomer data is stored in the US; by default traffic may be routed to select countries in the US, Europe, Asia and Australia. source
  • OfflineCowork runs tasks in an isolated virtual machine on the user's computer and can read and write only folders the user connects. source
  • RemoteTeam usage limits are per member, so one person hitting a limit does not affect colleagues. source

Gemini: worth knowing

  • SecurityGemini app chats and uploads from users with a Workspace license are not human-reviewed or used to train models; users signed in with personal Google accounts do not get this protection. source
  • RemoteAdmins can retain, hold, search and export Gemini app conversations with Google Vault regardless of user deletion settings. source
  • SecurityGemini Notebook data is stored as separate copies and is not covered by the organization's data region settings. source
  • RemoteThe Gemini desktop app for Mac requires macOS Sequoia 15 or later on Apple Silicon. source

Microsoft 365 Copilot: worth knowing

  • SecurityFor EU customers Copilot runs inside the EU Data Boundary; customers outside the EU may have queries processed in the US, EU or other regions. source
  • SecurityWeb-search queries that Copilot Chat sends to Bing fall outside the EU Data Boundary, which matters for EU teams with strict residency rules. source
  • RemoteCopilot in Teams is available on Windows, Mac, web, Android and iOS, so remote and in-office staff get the same meeting features. source
  • OfficeEven without a paid Copilot licence, Copilot Chat in Outlook can answer questions across a user's email, calendar, meetings and chats. source

Perplexity: worth knowing

  • RemotePerplexity says it never trains its models on enterprise customers’ data. source
  • RemoteEnterprise admins can set file retention, with automatic deletion as short as 1 day. source

Checked September 27, 2026 against each vendor’s own trust center, help docs and app pages. Hover or tap “source” to see the exact wording we relied on. “Not published” means we could not find the vendor saying it on its own site; it doesn’t mean the feature is missing. Plan names are the lowest plan the vendor says includes the feature. Security · Offline · Remote vs office · Download the data

Frequently asked questions

Which AI assistant tool is cheapest?

Of the 5 AI assistant tools HelpCompare tracks, the lowest published entry price belongs to Gemini (Included in Google Workspace from $7/user/mo (annual), verified September 19, 2026). Entry prices are the cheapest paid tier each vendor publishes; the right answer at your team size depends on seat minimums and add-ons, which each head-to-head comparison breaks down.

Which AI assistant tools have a free plan?

Free plans: ChatGPT (Free plan for individuals); Claude (Free plan for individuals); Gemini (Free Gemini app for personal Google Accounts; business use via Workspace); Microsoft 365 Copilot (Copilot Chat included with eligible Microsoft 365 business plans); Perplexity (Yes: search with citations and basic models).

Where does this pricing data come from?

Every figure was recorded from the vendor's own pricing page during research for a HelpCompare comparison, and is dated. The most recent check in this category was September 27, 2026. Nothing is estimated: where a vendor publishes no price, we say so. The full dataset is free to reuse under CC BY 4.0 at helpcompare.com/data/.

Sources

Figures come from each vendor’s pricing page, recorded on the date shown. Download the full dataset from Open Data (JSON and CSV, CC BY 4.0).

Cite this page: HelpCompare, “AI Assistants for Teams”, helpcompare.com/ai-assistants/ (updated ).

Source links on this site are checked every month; last check . How sources are checked.

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About the author

Bill Belcamino

Founder and author, HelpCompare

Engineer by training, operator by experience, marketer by choice. Bill spent eight and a half years as an engineer at HP, was COO of Auctiva (the number one third-party selling platform on eBay, past 200,000 users) and ran Google’s $70M/year search syndication partnership at Alot.com. Then he spent 13 years building his own web properties with his own money at stake. He has bought, trialled, integrated and cancelled more SaaS tools than he can count, and started HelpCompare because the real cost of switching tools is the part nobody covers.

“I’ve sat on both sides of the table: the agency recommending the tool and the client paying for it.”

Researched and fact-checked by the HelpCompare team. Pricing on this page was last verified on September 27, 2026. No paid sponsorships, no affiliate commissions.

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