How to plan a trip with AI (flights, hotels, routes, events)

Planning a trip takes days, sometimes weeks. You need to find flights and hotels, pick places and split them into days so you're not crossing the whole city back and forth. You also need to catch the right price: a day earlier or later, a ticket can cost a lot less. Sometimes a flight with a layover is cheaper than a direct one. Sometimes it's cheaper to take a train to a nearby city and fly from there.

AI takes this routine off your hands: it goes through dozens of options, compares prices and builds a route that fits your request. To work with real prices and availability, ChatGPT or Claude needs connectors to booking, ticket and map services.

What you get

• Interesting places that match your interests, with a short description of each
• A day-by-day route: places grouped by area, short transfers
• Flight options: direct, with layovers, from a nearby city
• Price comparison with dates shifted a couple of days either way
• Hotels with real prices and availability for your dates
• Public holidays taken into account: when places are closed or prices peak
• Concerts, games and shows on your travel dates
• A map with every stop on the route
• One finished plan instead of a dozen browser tabs

Step 1. Connect connectors

A connector gives AI access to a service's live data: dates, prices, availability. You turn them on in ChatGPT or Claude settings, in the apps and connectors section.

Almost all connectors below only search and compare. You book and pay yourself, through the link to the service's website.

Flights

Service	What it does	Works in	Link
Kiwi.com	Flight search, flexible dates, layovers, any class	Claude, ChatGPT*	kiwi.com
Expedia	Flights and hotels with real-time prices	ChatGPT*, Claude*	expedia.com
Skyscanner	Compares flights and prices, changes dates and airports	ChatGPT*	phocuswire.com
Trip.com	Flights, hotels, trains, attractions	ChatGPT*	trip.com

Hotels and stays

Service	What it does	Works in	Link
Booking.com	Hotels and apartments with prices, ratings and filters	Claude, ChatGPT	claude.com
Expedia	Hotels and rooms with prices and availability	ChatGPT*, Claude*	expedia.com
Tripadvisor	Compares hotels by reviews, prices and availability	Claude, ChatGPT*	tripadvisor.com
trivago	Prices for one hotel across many booking sites at once, price forecast	Claude, ChatGPT	trivago

Some popular services, like Airbnb, don't have official connectors yet. But AI with browser access can go to their website and search there directly.

Places, routes, maps

Tool	What it does	Works in	Link
Built-in maps	Show places and route stops on a map	ChatGPT, Claude	—
Viator	Tours, attractions and experiences, filtered by dates and price	Claude, ChatGPT*	claude.com
Tripsy	Trip planner: creates a trip, adds bookings and activities, rebuilds the route	Claude, ChatGPT	tripsy.app
Google Maps**	Place search, routes, travel time, weather	Any AI that supports MCP	developers.google.com
Mapbox**	Routes, travel time, maps	Any AI that supports MCP	mapbox.com

AI can put places in order without a separate tool: it groups stops by area and builds a logical sequence. With maps, distances and travel times are more accurate.

Events and holidays

Source	What it does	Works in	Link
Ticketmaster	Concerts, sports, theater, festivals on your dates	ChatGPT, Claude (20+ countries)	ticketmaster.com
StubHub	10M+ events, prices and seat availability	ChatGPT, Claude	stubhub.com
SeatGeek	Primary and resale tickets in one search	ChatGPT	businesswire.com
Holidays	AI finds them with web search, no separate connector needed	ChatGPT, Claude	—

* Not available in every country yet. Check if it's available where you are.

** For developers only for now: you need an API key. It's not hard to get — ask your AI to walk you through it.

Step 2. Give AI a detailed task

Copy the template and fill in your details. The clearer the limits, the fewer follow-up questions.

You are an experienced travel agent. Your job is to plan a trip for me based on my conditions: compare as many options as you can and put together the best one.

From: [departure city]
To: [city/country or "suggest options"]
Dates: [from … to …], flexible ± [2–3] days
Travelers: [number of adults/children]
Budget: [total / for flights / per night at the hotel]
Interests: [history, food, nature, museums, nightlife…]
Style: [relaxed / packed], [on foot / taxi / public transport]
Stay: [hotel/apartment], [area, rating from …, breakfast, etc.]

What to do:
1. Find flights. Compare prices on my dates and with dates shifted ± [N] days. Look at direct flights, layovers and flying from nearby cities if it's cheaper to get there by train. Show the 3 best options: price, times, layovers.
2. Check public holidays on these dates: what will be closed and when prices peak.
3. Find concerts, games and shows on my dates that match my interests.
4. Pick 3 hotels with prices and availability near the main places.
5. Make a day-by-day route: group places by area so transfers are short. Add approximate travel time between stops.
6. Draw a map with every stop and the hotel.
7. For each place, 1–2 sentences: what it is and why it's worth going.
8. At the end, a summary table: dates, flights, hotel, cost, booking links.

Step 3. Refine and book

• Ask to change what doesn't work: "no overnight layover", "hotel closer to the center", "drop the museums on day two".
• Ask to compare the two final options by total cost.
• Book through the links in the answer. Before paying, check the price, dates, cancellation terms and baggage on the website: the price may have changed.

Step 4. Keep everything at hand

Save what you find to Memocore, a shared memory for AI. It connects to ChatGPT and Claude.

While you're still planning. Save interesting flight options, hotels and places. When you come back to planning, you won't have to search for everything again.

Once everything is booked. Save dates, times, flight numbers, airlines, addresses and booking numbers. Then during the trip you can ask from your phone:

• "What's my hotel booking number?"
• "What time is my return flight and which terminal?"
• "Where to next on today's route?"
• "Give me a short history of this place"

Checklist

• Connectors are on: flights, stays, events
• The task includes dates, flexibility, budget, interests, departure city
• AI checked shifted dates, layovers, holidays and events
• The route is grouped by area, and there's a map
• Prices and terms double-checked on the website before paying
• Plan, tickets and bookings saved to Memocore