Updated: October 8, 2025


Core AI Tools - Head-to-Head Comparison

Feature ChatGPT Plus Claude Pro Perplexity Pro Microsoft 365 Premium Google AI Pro
Monthly Cost $20 $20 ($17 annually) $20 $19.99 $19.99
Best For General content & reasoning Long-form documents Research & sourced facts Office ecosystem integration Google Workspace users
Strengths GPT-5, o3 models, versatile Analytical, 200K context Real-time search, cited sources Full Office suite included 2TB storage, Gemini 2.5 Pro
Weaknesses Can be verbose No real-time web search Limited creative writing Requires Microsoft ecosystem Newer platform
Context Window 128K tokens 200K tokens Varies by source 128K tokens 1M+ tokens
File Uploads ✅ Images, docs, PDFs ✅ Large files (30MB) ✅ PDFs, audio, video ✅ Office files native ✅ Images, docs
Web Search ✅ Real-time ❌ Limited (Jan 2025 cutoff) ✅ Real-time with sources ✅ Real-time ✅ Real-time
Coding Help ✅ Excellent (Codex CLI) ✅ Excellent ✅ Basic ✅ Good ✅ Good
Data Analysis ✅ Advanced ✅ Advanced ✅ Research-focused ✅ Excel native ✅ Sheets native
Storage Included ❌ None ❌ None ❌ None ✅ 1TB per user (6 users) ✅ 2TB

What's New in October 2025:

ChatGPT:

Claude:

Perplexity:

Microsoft Copilot: