Best AI dictation apps of 2025 ranked: Wispr Flow, Willow, Monologue and more

Recent advancements in large language models (LLMs) and speech-to-text technology have led to significant enhancements in AI dictation applications. TechCrunch evaluated and ranked the leading choices: - Wispr Flow (available on macOS, Windows, iOS; Android version in progress) features custom styles and vibe-coding integration. It offers a free tier of 2,000 words per week (desktop) and 1,000 words per month (iOS), with unlimited access starting at $15/month. - Willow emphasizes user privacy, providing a free limit of 2,000 words per month, with unlimited options from $15/month. - Monologue utilizes on-device AI, offering 1,000 words per month for free, or a subscription for $10/month or $100/year. - Superwhisper allows for custom prompts, with a free basic voice-to-text option and paid plans starting at $8.49/month. - VoiceTypr operates offline, offering a free 3-day trial and a lifetime license for $35. - Aqua, backed by Y Combinator, provides low latency with a free limit of 1,000 words per month, and paid plans starting at $8/month. - Handy is an open-source option available for free. - Typeless allows for 4,000 words weekly, equating to approximately 16,000 words monthly for free, with a paid option at $12/month. - VoiceInk is also open-source, offering lifetime access for $25. - Dictato is a Mac dictionary app priced at €9.99 (~$12). - AudioPen has a pricing structure of $33 for three months, $99 annually, or $159 for two years.