ChatGPT vs sideOS
ChatGPT and sideOS are both AI assistants tools. ChatGPT is aimed at small businesses and creators, while sideOS is aimed at freelancers and developers. Only ChatGPT has a free plan.
OpenAI's conversational assistant
Voice-driven Mac agent in the notch with local dictation and meetings
| Pricing | Freemium · $8 | Paid |
| Starting price | $8/mo | Not published |
| Free plan | Yes | No |
| Free trial | — | — |
| Built for | Small businesses, Creators, Developers | Freelancers, Developers, Small businesses |
| Platforms | web, ios, android, macos, windows | macos |
| Country | US · 2022 | — |
| Rating | — | — |
Choose ChatGPT if
Knowledge workers, students and teams who want one general-purpose assistant with wide capabilities.
- Broadest feature set and app ecosystem
- Strong free tier
- Desktop and mobile apps are polished
Look elsewhere if: Workflows that need deterministic outputs or on-premise deployment; use APIs with structured outputs instead.
Choose sideOS if
Mac professionals who want a private voice agent, dictation and meeting notes in one app they pay for once.
- One-time licence with all future updates and no subscription
- No account and no sideOS server between you and the model
- Dictation and meeting transcription stay on the Mac
Look elsewhere if: Windows or mobile users and teams that need shared meeting notes or admin controls (Granola, Raycast).
ChatGPT vs sideOS pricing
ChatGPT
- Free$0Ad-supported, limited usage
- Go$8/moAd-supported, higher limits than Free
- Plus$20/moAdvanced models and features
- Pro (5x)$100/mo5x Plus usage
- Pro (20x)$200/mo20x Plus usage
sideOS
- Lifetime licence$89.90One-time; one Mac at a time, every future update included
- AI model usageVariesPaid to your own provider, about 2 to 5 cents per command
ChatGPT · Key features
- Chat with web search, citations and file/image analysis
- Deep Research for long-form multi-source reports
- Image generation and editing
- Advanced Voice mode and desktop apps
- Custom GPTs with Actions and a GPT Store
- Projects, memory and Business/Enterprise admin controls
Cons
- Usage limits on Plus for the best models
- Pro tier is expensive
- Hallucinations still require verification
sideOS · Key features
- Hold-to-talk agent that reads the screen, clicks, types and runs AppleScript
- On-device dictation into any app in 62 languages at no extra cost
- Meeting recording for Zoom, Meet and Teams with on-device Whisper and speakers
- Background tasks with web search, file access and approved shell commands
- Reminders that can complete a task before they fire
- One-click MCP connections for Gmail, Calendar, Notion, Slack and GitHub
Cons
- Apple Silicon Macs with macOS 14 or later only
- Agent use adds API costs unless you run a local model
- No free trial or refund window stated on the site
ChatGPT vs sideOS: FAQ
Do ChatGPT and sideOS have a free plan?
ChatGPT has a free plan. sideOS has no free plan.