LLMs (ChatGPT, Gemini, Claude) are reshaping travel planning but have different strengths and integrate in different ways with other travel ecosystem services.  Their surprising power is tempered by the need for careful verification for accuracy.

What is Happening to Travel

Travel planning is rapidly shifting toward AI-driven tools that both organize trips and adapt them in real time. Traditional booking platforms such as Booking.com and Expedia are responding by embedding themselves within large language models (LLMs) while also integrating AI directly into their own products. At the same time, startups are building new interfaces on top of LLMs and existing travel infrastructure.

What LLM Business Models Mean

LLMs need to make money and they are not doing that very well – or at least well enough given their spending.  So, they will make the same move as search engines did and add advertising.   They are likely to provide advertising supported free tiers and reduced or advertising-free subscription tiers.

External travel sites like booking.com are already anticipating pay-for-placement in LLMs.  Like search engines, advertisers may get more prominent placement than would otherwise be warranted.

The early evidence suggests that OpenAI and Google have different approaches to how a chatbot should sell. According to Similarweb, 98.5% of the ads in Google’s AI Mode appear in response to the user’s first query, rather like a conventional search engine. ChatGPT, by contrast, bides its time. Less than half its ads come in the chatbot’s first response, and nearly a third come after the tenth turn in the conversation—like a shop assistant waiting for the customer’s intent to become clear before they make their pitch. “This is not search. This is a new category of advertising,” argues Harel Amir of Similarweb.(“Why Your AI Assistant Is Suddenly Selling to You,” 2026)

The Different LLMs

When used directly for travel planning, the major LLMs have different strengths.

ChatGPT: Best for structured planning and integrated services. Operates as a platform with third-party app integrations (similar to an app store model). Users can invoke services like Booking.com directly within prompts. e.g., “Booking.com, find hotels in Paris for two adults…”.

Gemini: Strongest for real-time pricing and availability. Deeply integrated with Google’s ecosystem (Flights, Hotels) and can leverage personal data such as Gmail and Calendar when enabled in Gemini.  A new feature in Google Maps called “Ask Maps” which allows more complicated dialogues around a map location, for example:

On a rainy day in Hong Kong, I opened Google Maps, tapped the “Ask Maps” button and typed, “It’s rainy. Find activities to do with a toddler nearby.” The app suggested a visit to the science museum and gave me directions to walk there in 10 minutes. My daughter, who is not easily entertained, squealed with delight at the robotic dinosaurs. (Chen, 2026)

Claude: Excels at thoughtful, narrative itinerary design with a lower hallucination rate. Uses an open ecosystem where users connect external services.

How they stack up:

Capability	ChatGPT	Gemini	Claude
Travel app integrations	Third-party apps (e.g., Booking.com, Expedia)	Google-native (Flights, Hotels, Maps)	Connector-based (Booking.com, Tripadvisor, Viator, AllTrails)
Booking inside chat	Partial (search + handoff to provider)	No (always redirects)	No (advisory + connector use)
Flight search	Via apps or links	Native (Google Flights)	Indirect (advice, connectors)
Hotel search	Strong via apps	Native (Google Hotels)	Via connectors
Activities / experiences	Moderate (depends on apps)	Strong via Maps/Search	Strong (Viator, AllTrails)
Real-time pricing accuracy	Medium–high (app-dependent)	High (Google data)	Medium (depends on connectors)
Itinerary building	Strong, structured, customizable	Strong, data-driven	Very strong, detailed and thoughtful
Personalization / memory	Strong persistent memory	Strong via Google ecosystem	Moderate (session or connector-based)
Ease of use	Very high (single interface + apps)	Very high (especially if using Google tools)	Moderate (requires connecting services)
Best use case	End-to-end planning + booking handoff	Search + logistics + navigation	Designing high-quality itineraries

Other Apps and Sites

Existing large traffic travel sites such as Booking.com and Expedia are integrating to appear within LLMs.  They are also incorporating AI when they are used from their own sites.   For example, Booking.com has an AI Trip Planner that integrates ChatGPT. (Hamilton, 2025)

Startups are providing different user interfaces on top of LLMs and other travel industry infrastructure.  Examples include:

• Travo – a mobile device app for the social networking focused crowd – “Skip the tourist traps. Travo surfaces real places from Instagram, TikTok, and YouTube — spots that real travelers and creators are posting about. Add them to your trip in one tap.”
• Layla and Wonderplan – generate multi-day itineraries.  These can be a jumping off point for more detailed work.
• Tripplanner – allows multiple users to vote on activities and split costs within the tool.

Best Practices

Exploration

AI can be helpful in suggesting trips you hadn’t thought of or providing ideas in regions that you aren’t familiar with.  One WSJ reporter wanted a weekend getaway and discovered Saltburn-by-the-Sea in North Yorkshire after asking “Find me a two-night seaside getaway from London in mid-March. No tourist traps, Instagram hot spots or luxury hotels.”(Gilbertson, 2026)

Prompt Engineering

Once you are ready for some detailed planning, the usual rule holds – be voluble and explicit in your prompts, and don’t be afraid to tell the LLM to double check its work.   Example prompt:

Please carefully check multiple sources to confirm all your information is current and correct. Make sure there is reasonable cushion time between transportation transfers, to allow for slight delays and time for bathroom breaks and time to get to the next departure point. Please keep the following of my personal preferences in mind: I am a vegetarian foodie and coffee lover on a budget and I enjoy walking, being in nature, vintage stores, museums, live music and avoiding touristy places like Las Vegas, theme parks or Times Square. I strongly dislike high humidity. I prefer inexpensive but highly rated short-term rentals (private room and bathroom required) or boutique hotels below U.S. $200 per night. Safety is important, so no high-crime neighborhoods to save money. I prefer to be walking distance from the heart of an area, instead of in the suburbs. I will have one carry-on sized backpack bag.

Try to include:

• Logistics: Exact dates, budget (e.g., “$150/day for activities”), and travel companions (e.g., “traveling with a toddler”).
• Vibe & Pace: Define the “intensity” (e.g., “1-2 activities per day with long lunch breaks”) and specific interests (e.g., “Gaudi architecture but avoid heavy tourist crowds”).
• Negative Constraints: Explicitly state what to avoid (e.g., “no early morning flights” or “no non-accessible stairs”). 

Have in mind leaving some room for serendipity – things that AI (or even other research) doesn’t know that you discover on the ground.

A poem by Matthew Kelly (Gilbertson, 2026)

I’d rather step outside with nary a clue,

Then have an AI tell me what to do.

AI is kind, and sometimes quite right,

But not knowing what’s next makes the trip a delight.

‘AI will only get better!’ is what people say,

But I like a journey where I find my own way.

So follow AI if that’s what you like,

But I’d rather see Claude take its own hike.”

Good Tasks for AI

• Define your goals: use AI to tailor the trip around interests like history, food, nature, budget, or pace.  “Plan a relaxed Provence trip for Sept 25–30 focused on markets, Roman history, scenic villages, good food, and moderate walking.”
• Build an itinerary: generate a day-by-day plan with logical routing and realistic timing.  “Create a 6-day itinerary: Marseille arrival and Vieux-Port, Aix markets and Cézanne sites, Arles Roman monuments, Camargue day trip, Luberon villages, departure.”
• Compare destinations: evaluate weather, costs, crowds, safety, and seasonal events.  “Compare Marseille, Aix-en-Provence, and Arles in late September for weather, crowd levels, cultural attractions, and ease of travel.”
• Find flights and lodging: screen options by price, convenience, walkability, and amenities.  “Find the best open-jaw flight into Marseille Provence Airport and recommend centrally located boutique hotels near Vieux-Port, Aix old town, and Arles center.”
• Optimize transportation: map trains, rental cars, transit passes, or scenic drives. “Should I use trains, buses, or a rental car between Marseille, Aix, Arles, and nearby villages like Gordes or Saint-Rémy?”
• Discover local highlights: surface attractions, hidden gems, festivals, and neighborhood character.  “What are the best late-September experiences in Provence—Calanques boat tours, Aix markets, Arles amphitheater, Camargue flamingos, or vineyard visits?”
• Personalize dining: recommend restaurants based on cuisine, budget, and reservation needs.  “Recommend authentic bouillabaisse in Marseille, Provençal bistros in Aix, and outdoor dining in Arles under €40 per person.”
• Manage logistics: track bookings, packing lists, travel documents, and budget estimates.  “Create a budget for Sept 25–30 including airfare, hotels, train tickets, museum passes, meals, and daily spending.”
• Prepare on the ground: translate phrases, explain customs, suggest tipping norms, and flag scams.  “Teach me useful French phrases for hotels, cafés, train stations, and markets, plus local customs and tipping etiquette.”

• Adapt in real time: rework plans for weather, closures, fatigue, or spontaneous opportunities.  “If mistral winds close the Calanques or rain affects Arles, suggest indoor alternatives like MuCEM, Carrieres des Lumières, or wine tastings.”
• Baseline packing list:  may well suggest things you wouldn’t have thought of but be careful to augment with things it misses.  “Create a detailed packing list for a 7-day trip to Provence, France in late September. I will be staying in Nice, Aix-en-Provence, and Arles, using trains between cities. My activities will include walking tours, light hiking, biking, visiting museums, and dining at local restaurants.”
• Things to do before traveling;  similar to packing list, catch things you might not have thought of. “Create a concise checklist of everything I should arrange before a one-week trip to Provence, France, including travel documents, reservations, health preparations, finances, and home logistics. Prioritize time-sensitive tasks and include brief notes on when each item should be completed before departure.”
• Stress test: test an itinerary: “Find any logistical flaws, such as activities located too far apart or likely closure times.”
• Get Help with Complicated Loyalty Programs:  LLMs can do surprisingly well at picking through rules though you will have to double check the results.   An example:

My wife has her 50th birthday this fall. I play a lot with credit card bonuses, free night awards. I had two 85,000 [point] certificates from Marriott as well as two free night awards with Hilton. I asked Gemini to find me four different options for a nice luxury vacation that I could use all four of my free nights in one area. It found four great locations in Mexico that would match up nicely. For Hilton, it found the Waldorf Astoria Los Cabos Pedregal. So it helped me book about $7,000 of free night awards just from a Gemini prompt. (Gilbertson, 2026)

Simple reservations: LLMs can handle some simple reservations like restaurants (through OpenTable/Resy) and event ticket bookings through simple text prompts. “Find a table for two at Chez Bruno on Saturday, September 26 at around 7:30 PM and provide available reservation options. If possible, complete the booking on my behalf using OpenTable or the restaurant’s reservation system, and confirm the reservation details.”

Hallucinations and Verification

Yes, hallucinations happen, and often, so you need to exercise verification hygiene.  Risky areas include:

• Flight availability and pricing: Quoting fares, seat classes, or routes that changed minutes ago or were cached incorrectly.
• Hotel availability and amenities: Inventing room types, breakfast inclusion, parking, airport shuttles, or cancellation terms.
• Train, ferry, and transit schedules: Misstating departure times, seasonal routes, strike impacts, or transfer feasibility.
• Geography and routing: Underestimating travel times, suggesting unrealistic same-day combinations, or confusing similarly named places.
• Visa, passport, and entry rules: Incorrect assumptions about visa-free entry, passport validity windows, ETIAS/eVisa requirements, or health forms.
• Opening hours and closures: Recommending museums, restaurants, or attractions without accounting for holidays, Mondays, renovations, or seasonal shutdowns.
• Local events and festivals: Inventing or misdating markets, concerts, festivals, or special exhibits.
• Safety and customs advice: Overgeneralizing neighborhoods, missing local scams, or misstating tipping norms and dress expectations.
• Weather assumptions: Treating historical averages as forecasts or missing extreme seasonal events (heat waves, monsoons, wildfire smoke).
• Budget estimates: Ignoring taxes, resort fees, baggage fees, tolls, exchange-rate changes, or peak-season surcharges.
• Loyalty programs and fare rules: Misunderstanding points redemption, baggage allowances, seat selection, cancellation options or refundability.
• Restaurant recommendations: Suggesting closed, relocated, tourist-trap, or poorly matched dining options.
• Language/translation nuance: Producing technically correct but culturally awkward phrases or misunderstanding local terminology.
• Complex multi-stop itineraries: Creating schedules that look elegant on paper but fail under real-world transfer times or fatigue.
• Emergency logistics: Overstating medical access, evacuation options, or travel insurance coverage.

Use AI for research, drafting, and optimization, but verify the high-risk areas above directly with:

• Airline / rail / hotel official sites
• Government travel advisories
• Embassy or visa portals
• Google Maps / local transit apps
• Recent reviews and official attraction websites

Note that AI can over simplify to averages on things like weather and politics – it won’t necessarily consider unlikely but significant possible events like storms or wars.   If there is any likelihood of an extreme event, engage in a dialogue that forces consideration and optionality.

Cross-reference top AI picks on Reddit or TripAdvisor to ensure a “top-rated” spot isn’t actually a tourist trap. 

AI is strongest at narrowing options and structuring plans; it is weakest where data changes constantly or rules have legal consequences.

References

Chen, B. X. (2026, April 30). A Tech Writer Puts Google’s A.I. to the Test as a Trip Planner. The New York Times.

Gilbertson, D. (2026, March 24). I Let AI Plan My Seaside Break and Wound Up Swimming in the North Sea. The Wall Street Journal.

Hamilton, K. (2025, December 29). Booking Awaits OpenAI. The Wall Street Journal.

Why your AI assistant is suddenly selling to you. (2026, April 19). The Economist.