A black-haired woman in an orange sweater sits on the living room as she uses a laptop on the coffee table.

AI is changing the way we plan trips. With tools like KAYAK’s AI Mode, travelers can skip the endless scrolling and get instant, personalized, data-backed recommendations. But here’s the thing: to get the best results, you’ve gotta know how to talk to it.

Think of your prompt like talking to a really sharp travel expert – one who actually listens. The clearer you are about what you want (where, when, vibe, budget), the better your results – and your savings – will be.

Here’s how to write prompts that do the heavy lifting for you.

1. Be specific. Details lead to deals.

Unlike traditional search filters where you’re limited to checkboxes like “pool” or “free breakfast,” AI Mode can understand exactly what you mean. Try going deeper with your descriptions:

Find a boutique hotel with a pool near the Wynwood Art District, under $250 per night.

Adding concrete details about what you care about – location, amenities, budget or even your vibe – helps the AI zero in on results that actually fit.

icon light-bulb

Pro tip from KAYAK AI engineers:

LLMs (large language models, like ChatGPT) thrive on constraints, so instead of saying “plan me a trip to Italy,” you’ll get a more bespoke response if you provide the pieces you value the most. For example, try “Help me plan a trip to Italy. I care more about food and architecture than beaches. What cities should I prioritize?

2. Set the vibe.

Here’s where the magic really happens. KAYAK’s AI tools combine ChatGPT’s conversational power with KAYAK’s real-time travel data. That means you can ask very specific questions – and get instant, data-backed answers.

Find a romantic adults-only hotel in Santorini with ocean views and a spa.

When you set the vibe, you help the AI recommend not just where to go but how it should feel once you get there.

Two lovers in casual clothes stand and hug on a balcony gazing at the terraced buildings set on hills.

3. Dig into data. 

KAYAK’s AI tools fuse ChatGPT’s natural language understanding with KAYAK’s powerful travel data. That means you can ask questions like:

What are the best times to book flights for spring break to get the lowest fares?

It’s like chatting with your stats-obsessed travel buddy who always knows when to book and when to wait.

icon light-bulb

Pro tip from KAYAK AI engineers

It never hurts to ask why. Asking AI Mode questions like “Why is Paris cheaper in the fall?” or “Why would I want to go to Prague at the time of year you’ve recommended?” help you feel confident in your travel decisions.

A curly-haired person in a black dress stands in front of an airport flight information display.

4. Personalize your output.

Your travel planning style is unique and AI can adapt to it. Want a chart, a list or even a full itinerary? Just ask.

Show me a chart comparing NYC to LA flight prices by day.

AI tools are flexible – ask for summaries or even itinerary-style breakdowns.

icon light-bulb

Pro tip from KAYAK AI engineers

Don’t be afraid to ask for iterations. Instead of saying “Give me a 7-day itinerary in Tokyo“, try “Draft a rough 7-day itinerary for Tokyo focused on design, culture and food.” Once the tool provides the results, you can further refine with a prompt like “Add a day trip to Kyoto and drop anything too touristy.

5. Think like an insider.

A man in sunglasses, denim jacket, and black pants leans on a promenade railing while using his smartphone.

Use AI to uncover hidden deals and lesser-known insights – the kind only data can reveal. Try a prompt like:

Which European cities have the lowest airfare from New York this fall?

This kind of question turns AI into your personal travel strategist.

Plan smarter, not harder.

AI can’t pack your suitcase (yet) but it can save you hours of planning and help you find the best deals. By mastering the art of the AI travel prompt – being specific, setting the scene, using data, and personalizing your output – you can plan faster, spend smarter and travel better.

Next time you’re planning a trip, let KAYAK’s AI Mode work its magic.

About the author

KAYAK Since 2004, KAYAK has been revolutionizing the travel industry. Metasearch for travel? No one was doing it. Until we did. Today, we process billions of queries across our platforms each year for travel information, helping millions of travelers around the globe make confident decisions. With every query, KAYAK searches hundreds of travel sites to show travelers the information they need to find the right flights, hotels, hire cars and holiday packages.

Explore more articles

Want to know the world better? We got you covered.

Sign up for our newsletter and get more travel inspiration straight to your inbox each week