Head to head 2026 edition
ChatGPT vs Sidekick Pro
One is the chatbot everyone already uses. The other is an assistant that answers your phone, watches your inbox and works in your own browser. Here is where each one wins.
ChatGPT
General-purpose AI chatbot by OpenAI
From $8/mo
Best for Writing, research and turning a goal into finished documents, sheets and slides.
Visit ChatGPT
Sidekick Pro
AI agents for your email, calendar, calls and browser
From $59/mo
Best for Professionals and small teams who want email, calls, meetings and web chores handled for them.
The short answer
ChatGPT or Sidekick Pro: which should you use?
Choose ChatGPT if you want the best general chatbot for writing, research and turning a goal into finished documents. Choose Sidekick Pro if you want an assistant that works without being asked: it flags important email, answers your business phone, joins your Zoom and Google Meet calls, and clicks through web tasks in your own Chrome, on GPT, Claude or Gemini, from $59 a month.
ChatGPT starts at $20 a month and Sidekick Pro at $59, and both can now take actions, not only answer questions. The difference is where the work starts. ChatGPT waits for you to bring it a task. Sidekick Pro is connected to your inbox, calendar, phone line and browser, and it brings work to you.
We compared the two on the jobs people actually hand an assistant: email and calendar, web tasks that need your logins, phone calls and texts, meetings, memory, team use and price. We used each vendor's own pricing and feature pages, and we say where ChatGPT is the better pick.
ChatGPT vs Sidekick Pro, feature by feature
Prices and features come from each vendor’s own site. ChatGPT pricing was last checked on September 23, 2026.
| Feature | ChatGPT | Our pick Sidekick Pro |
|---|---|---|
| Price | ||
| Starting price | From $8/mo | From $59/mo |
| Free plan | Yes | No |
| Plans | Go $8/mo · Plus $20/mo · Pro $200/mo · Business $25/user/mo | Personal $59/mo · Business $149/mo |
| Email and calendar | ||
| Reads Gmail and Google Calendar | Via connectors | Yes |
| Flags important email without being asked | No | Yes |
| Daily brief and calendar alerts | No | Yes |
| Drafts replies for you to approve | When you ask | Yes |
| Browser and web tasks | ||
| Works in your own browser with your logins | Desktop app browser | Your own Chrome |
| Keeps working with your computer off | Cloud browser | Private cloud browser |
| Other agents can drive it (MCP) | Not listed | Yes |
| Phone, texts and meetings | ||
| Answers your business phone | No | Every plan |
| Sends and replies to texts for you | No | Every plan |
| Joins Zoom and Google Meet calls | No | Business plan |
| Records and transcribes meetings | Record mode, desktop | Business plan |
| Models and memory | ||
| Choose your AI model | OpenAI models only | GPT, Claude, Gemini |
| Remembers you across conversations | Yes | Yes |
| Image generation | Yes | Yes |
| Voice conversation | Yes | Yes |
| Teams and apps | ||
| Shared team workspace | Business plan | Business plan |
| Shared skills or agents | Workspace agents | Business plan |
| Connect apps (Slack, Notion, GitHub) | Yes | Yes |
| Apps | Web, iOS, Android, Mac, Windows | Web, Chrome, iOS, Android, Mac, Windows, Apple Watch |
Head to head, topic by topic
Who starts the work
ChatGPT
ChatGPT is a place you go to get work done. It is excellent once you ask, but it does not watch your inbox or calendar and tell you what needs attention. Workspace agents on the Business plan can run on a schedule, but someone has to build them first.
Sidekick Pro
Sidekick Pro reads every new email and calendar change as it arrives, alerts you to what matters, and sends a daily brief. It drafts the reply or starts the task, and nothing goes out without your OK. You get the help before you think to ask.
Web tasks that need your logins
ChatGPT
ChatGPT Work, which replaced agent mode in July 2026, runs a browser in OpenAI's cloud that stays signed in between chats. It is strong at research that ends in a document. Sites you use every day need you to sign in again inside that browser.
Sidekick Pro
Sidekick Pro works in the Chrome you already use, with the logins you already have, so there is nothing to set up again. For long jobs it can also use a private cloud browser that keeps working with your laptop closed. You can start a task by voice or from your phone.
Phone calls, texts and meetings
ChatGPT
ChatGPT does not answer a phone line or text your customers. On the desktop app, Record mode transcribes a meeting you are in, but ChatGPT does not join a call on its own.
Sidekick Pro
On every plan, Sidekick Pro gets its own phone number. It answers calls and texts as your receptionist, books appointments, and transfers the calls that need you. On the Business plan it also joins your Zoom and Google Meet calls, takes notes and follows up.
Models and memory
ChatGPT
ChatGPT runs on OpenAI's models only. Its memory carries your preferences between chats, and projects keep files and instructions together.
Sidekick Pro
Sidekick Pro lets you pick GPT, Claude or Gemini, or let it choose the best model for each turn. One subscription covers all of them. Its memory follows you across the web app, the extension, your phone and the phone line.
Teams
ChatGPT
ChatGPT Business starts at two seats at $25 each, with shared projects and workspace agents that teammates build once and share. OpenAI retired group chats in July 2026.
Sidekick Pro
The Business plan includes unlimited teammates at no extra cost, at one flat price of $149 a month. Teams share skills, documents, pages and data tables, and each person keeps their own private assistant and memory. Personal is for one person.
Which should you choose?
Choose ChatGPT if you
- mostly need writing, research and analysis
- want finished documents, sheets and slides from one prompt
- already use ChatGPT's connectors and custom GPTs
- want a free plan or the lowest entry price
Choose Sidekick Pro if you
- want your inbox and calendar watched for you
- need your business phone answered and texts handled
- want an assistant in your Zoom and Google Meet calls
- do web tasks that need the logins in your own Chrome
- want GPT, Claude and Gemini in one subscription
Our verdict
ChatGPT is the better chatbot. Sidekick Pro is the better assistant.
If what you need is a brilliant writer and researcher that you open when you have a question, ChatGPT is hard to beat, and its free plan makes it easy to start.
If what you need is help with the work that arrives on its own, the email, the calls, the meetings and the web chores, Sidekick Pro does that job and ChatGPT does not. It costs $59 a month to start, more than ChatGPT Plus, and it runs on GPT too.
Frequently asked questions
Does Sidekick Pro use ChatGPT's models?
Yes. Sidekick Pro runs on OpenAI's GPT models as well as Anthropic's Claude and Google's Gemini. You pick one, or let Sidekick Pro choose the best model for each request. One subscription covers all of them.
Can ChatGPT read my Gmail and calendar?
Yes, through its Gmail and Google Calendar connectors, when you ask it to. It does not watch your inbox on its own. Sidekick Pro reads each new email as it arrives and alerts you only when something needs you.
Can ChatGPT answer my business phone?
No. ChatGPT does not give you a phone number or answer calls for your business. Every Sidekick Pro plan includes an AI receptionist on its own number that answers calls and texts, books appointments and transfers calls to you.
Which one works in my own browser?
Sidekick Pro works in the Chrome you already use, with your own logins, through its Chrome extension. ChatGPT Work uses a browser in OpenAI's cloud and in its desktop app, where you sign in to sites separately.
How do the prices compare?
ChatGPT has a free plan, Go at $8 a month, Plus at $20, Pro at $200 and Business at $25 a seat. Sidekick Pro has Personal at $59 a month for one person, Business at $149 for a whole team with meetings and the coding agent, and Enterprise by contact sales. Sidekick Pro has no free plan or trial, and Business is one flat price however many members you invite.
Can I use both?
Yes. Many people keep ChatGPT for writing and research and use Sidekick Pro for email, calls, meetings and web tasks. Sidekick Pro can also connect to the same apps you use with ChatGPT.