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ChatGPT can plan your dream getaway—if you know how to ask

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August 2025

ChatGPT can create itineraries, compare connections, and give you insider tips. Here's how to use the Al correctly for holiday planning.

- BY FLORIAN KASTNER & SAM SINGLETON

ChatGPT can plan your dream getaway—if you know how to ask

Planning a trip takes time and often it's more of a hassle than you'd like. If you don’t feel like spending hours researching, you can simply outsource the first draft of your holiday plans to ChatGPT (fave.co/3U8OiV9). The chatbot suggests travel destinations, creates daily plans, compares means of transport, reminds you about charging devices, and even virtually packs your suitcase.

But how reliable are these suggestions? And can it actually save you money? We'll show you what ChatGPT excels at in vacation planning—and warn you of pitfalls where it stumbles. Let's dig in.

FIND TRAVEL IDEAS

If you don’t have any concrete plans yet, ChatGPT is an excellent starting point for finding ideas. Start with a few wishes or questions such as:

  • I would like to travel with two friends for five days in September, budget maximum $300 per person. We would like nature and hiking, but also a small city to stroll around.

  • Which three European cities are cheap, family-friendly, and under $400 in autumn?

  • I'm planning a seven-day round trip from Munich through South Tyrol, the Dolomites and Lake Garda with activities and accommodation.

ChatGPT responds with a list of suitable destinations as well as information on traveling, accommodation costs, local activities and much more—depending on the initial question or prompt (command).

When making hotel suggestions or flight connections, remember that the AI does not process real-time data. You have to check for yourself whether the specified bus connection still exists, a cheap flight is actually available, or the accommodation is out of budget in high season. In this aspect, the time saved by using ChatGPT is less than hoped for (at least if you want to accept the suggestions unfiltered).

The AI can also provide you with links to the official hotel websites, but you have to make the bookings yourself.

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