AI Chat Assistants: ChatGPT, Claude, Gemini, Grok, and Specialist Tools
5 tools · listed in dataset order, no ranking
This category lists four general-purpose AI assistants, ChatGPT, Claude, Gemini, and Grok, and one specialist conversational app, FreeSay, for practising a spoken language. The general assistants overlap heavily: all four write, answer questions, work with uploaded files and images, offer voice conversation, and have free plans with usage limits. The useful differences are which apps and accounts each one connects to, what each plan includes, and how each handles your data. FreeSay is not a substitute for them; it is a speaking-practice app you would use alongside one.
ChatGPT
OpenAI
AI Assistant & Productivity Platform
Best for: Knowledge workers who need one AI subscription covering writing, research, coding, image generation, and team collaboration
Claude
Anthropic
AI Coding & Reasoning Assistant
Best for: Developers and writers who need the most accurate code generation, precise instruction following, and the ability to reason across very large documents
Gemini
Multimodal AI Assistant
Best for: Research with real-time data, Google Workspace users, and multimodal tasks
Grok
xAI
AI Assistant with Real-Time X Integration
Best for: Users who need real-time social context from X alongside a capable general-purpose AI assistant
FreeSay
Fasterwork (Dae Jun Park)
AI Speaking Practice in 15 Languages
Best for: Language learners who need affordable speaking practice on a phone, including low-spec Android devices
How to choose an AI chat assistant
Start with what you will use it for
For writing, summarising, and questions about your own files, any of the four general assistants can do the job, so test them on your own material rather than relying on rankings. The differences show up around the edges. Gemini connects to Google apps such as Gmail, Calendar, and Maps, works inside Gmail on Google AI plans, and works inside Docs from AI Pro. Claude includes connectors and file creation with code execution on its free plan, and adds Claude Code and Research on paid plans. ChatGPT has a Chat mode for conversation and a Work mode for multi-step tasks such as research, documents, and spreadsheets. Grok includes image and video generation through Grok Imagine and is sold within xAI's X subscription. If you mainly want to practise speaking a language, FreeSay is built for that.
Check the plan, not just the product
All four have free plans with usage limits, and features move between tiers. Claude Code and Claude's Research feature need a paid Claude plan. Gemini's context window depends on the plan: 32,000 tokens without a Google AI plan, 128,000 on AI Plus, and 1 million on AI Pro and Ultra. ChatGPT's cloud browser is not on the Free or Go plans. Grok's paid plans draw on one weekly usage allowance shared across xAI's products. Long documents and heavy daily use are where free plans tend to run out first, so check the current plan page before you commit.
Web search and privacy settings differ
Claude, ChatGPT, and Gemini document built-in web search, and Claude lists it on its free plan. xAI's Grok help pages do not describe web search in the consumer app, though xAI's API offers web and X search tools. On data use, Claude's consumer plans let you opt out of model training with the Model Improvement setting. Gemini stops using future chats for training when you turn off Keep Activity, though it keeps them for up to 72 hours. ChatGPT keeps its controls under Settings > Data controls and offers temporary chats. OpenAI's Business and Anthropic's Team plans do not train on your data by default, and Google does not use Workspace data to train models outside your organization without permission.
Compare by connections, inputs, web search, privacy, and plans
The four general assistants, using what each vendor publishes in its own docs and pricing pages, checked on October 20, 2026. Plans and features change often, so confirm on the vendor's site before you buy. FreeSay is a specialist app and is covered in the guide and FAQ instead.
- Connects to
- Plugins that bundle skills and MCP connections to services such as Google Drive, GitHub, and Slack; availability depends on account and workspace
- Plans (USD per month)
- Free; Go $8; Plus $20; Pro from $100; Business $20/user billed annually
- Files, images, and voice
- Images and files; the new ChatGPT Voice in the desktop app is on Plus and above
- Web search
- Built-in web search with citations; cloud browsing in Work is not on Free or Go
- Training on your chats
- Settings > Data controls and temporary chats; Business and Enterprise data not used for training by default
- Connects to
- Connectors on every plan, including Free; Claude in Chrome and Microsoft 365 from Pro
- Plans (USD per month)
- Free; Pro $20 ($17 billed annually); Max from $100; Team $25/seat ($20 billed annually)
- Files, images, and voice
- Files and images; voice mode on Free; creates and edits files with code execution
- Web search
- Included on Free, Pro, and Max
- Training on your chats
- Consumer plans: opt out with the Model Improvement setting; Team: no training by default
- Connects to
- Connected Apps such as Gmail, Calendar, Maps, and YouTube (most need Keep Activity on); Gemini in Gmail on Google AI plans and in Docs from AI Pro
- Plans (USD per month)
- Free; Google AI Plus $4.99; AI Pro $19.99; AI Ultra from $99.99 (US)
- Files, images, and voice
- Documents and images; Gemini Live with camera and screen sharing
- Web search
- Built on Google Search; Deep Research on the free plan, subject to limits
- Training on your chats
- Turn off Keep Activity to stop future chats being used for training (kept up to 72 hours)
- Connects to
- Connectors for all users, including Gmail, Google Drive, OneDrive, Outlook, Salesforce, and custom MCP servers
- Plans (USD per month)
- New customers: the X Subscription, Free; Plus $8; Premium $30; Super $100; Ultra $200. Existing SuperGrok and X Premium plans continue
- Files, images, and voice
- Files up to 150 MB (PDFs, images, spreadsheets, code, audio, video); hands-free voice
- Web search
- Not described in xAI's consumer help docs; xAI's API offers web and X search tools
- Training on your chats
- Data Controls in settings; xAI's help docs do not say whether consumer chats train models
| Tool | Connects to | Plans (USD per month) | Files, images, and voice | Web search | Training on your chats |
|---|---|---|---|---|---|
| ChatGPT | Plugins that bundle skills and MCP connections to services such as Google Drive, GitHub, and Slack; availability depends on account and workspace | Free; Go $8; Plus $20; Pro from $100; Business $20/user billed annually | Images and files; the new ChatGPT Voice in the desktop app is on Plus and above | Built-in web search with citations; cloud browsing in Work is not on Free or Go | Settings > Data controls and temporary chats; Business and Enterprise data not used for training by default |
| Claude | Connectors on every plan, including Free; Claude in Chrome and Microsoft 365 from Pro | Free; Pro $20 ($17 billed annually); Max from $100; Team $25/seat ($20 billed annually) | Files and images; voice mode on Free; creates and edits files with code execution | Included on Free, Pro, and Max | Consumer plans: opt out with the Model Improvement setting; Team: no training by default |
| Gemini | Connected Apps such as Gmail, Calendar, Maps, and YouTube (most need Keep Activity on); Gemini in Gmail on Google AI plans and in Docs from AI Pro | Free; Google AI Plus $4.99; AI Pro $19.99; AI Ultra from $99.99 (US) | Documents and images; Gemini Live with camera and screen sharing | Built on Google Search; Deep Research on the free plan, subject to limits | Turn off Keep Activity to stop future chats being used for training (kept up to 72 hours) |
| Grok | Connectors for all users, including Gmail, Google Drive, OneDrive, Outlook, Salesforce, and custom MCP servers | New customers: the X Subscription, Free; Plus $8; Premium $30; Super $100; Ultra $200. Existing SuperGrok and X Premium plans continue | Files up to 150 MB (PDFs, images, spreadsheets, code, audio, video); hands-free voice | Not described in xAI's consumer help docs; xAI's API offers web and X search tools | Data Controls in settings; xAI's help docs do not say whether consumer chats train models |
Prices are the vendors' published US figures, monthly unless noted. Editorial comparison, not a ranking.
Common questions about AI chat assistant tools
What is the difference between ChatGPT and Claude?
Both are general assistants for writing, analysis, coding, and questions about your files, and both have free plans, web search, and connections to other apps. The practical differences are in how they package extra work: ChatGPT has a separate Work mode for multi-step tasks and plugins that bundle skills with MCP connections, while Claude includes connectors and file creation on its free plan and adds Claude Code and Research on paid plans. We do not rank them on writing or reasoning quality; try both on a sample of your own work.
Which AI assistants can search the web?
Claude lists web search on every plan, including Free. ChatGPT has a built-in web search tool that shows citations, and Gemini is built on Google Search. xAI's help docs do not describe web search in the Grok app, so check it yourself before relying on it for current events. If the sources matter more than the conversation, Perplexity searches the web for every question and numbers its citations. See AI research tools →
Are free plans enough?
For occasional use, often yes. All four general assistants have free plans with usage limits. Gemini without a Google AI plan has a 32,000-token context window, Claude's free plan does not include its largest models or Claude Code, and ChatGPT and Grok cap free usage. Heavy daily use, long documents, and agent features are where a paid plan usually becomes necessary.
Can I stop an assistant from training on my chats?
On Claude's consumer plans, turn off the Model Improvement setting; incognito chats are not used for training. On Gemini, turn off Keep Activity, though chats are still kept for up to 72 hours. ChatGPT's settings are under Data controls, and temporary chats are available. Business plans from OpenAI and Anthropic do not train on your data by default. xAI's help docs point to Data Controls in Grok's settings but do not say whether consumer chats are used for training.
Which assistant has the largest context window?
There is no single answer, because vendors publish limits by plan and model. Claude lists up to 1 million tokens depending on the model, and Gemini lists 1 million tokens on Google AI Pro and Ultra but 32,000 without a Google AI plan. OpenAI and xAI do not publish one consumer figure in the docs we checked. Compare the limit on the plan you would actually buy.
Is FreeSay an alternative to ChatGPT?
No. FreeSay is a mobile app for Android and iOS for spoken practice in 15 languages, with a few free minutes of conversation a day and a low-cost premium plan for unlimited practice. It does not do the writing, research, or file work of a general assistant. Use it alongside one, not instead of one. See FreeSay →
Related
- Browse AI research tools
Perplexity, Elicit, Consensus, and Gemini Notebook, for questions where sources matter most.
- Browse AI productivity agents and assistants
AI built into Microsoft 365, Notion, and other work apps, plus agents that finish multi-step tasks.
- Browse AI coding agents
Claude Code, OpenAI Codex, and other coding agents that come with some assistant plans.
Vendor facts in this guide last checked October 20, 2026 against: ChatGPT plans, ChatGPT web search, ChatGPT plugins, ChatGPT Voice, Claude plans, Claude model training, Google AI plans, Gemini limits, Gemini Connected Apps, Gemini Apps activity, Grok overview, Grok connectors, X Subscription pricing, FreeSay. Picks and tradeoffs are editorial judgments.