ChatGPT: Travel

Compare Disney World trip budgets from three AIs with ChatGPT, Gemini and Perplexity

Amanda Caswell gave ChatGPT, Gemini and Perplexity the same prompt: plan a five-day Walt Disney World trip for a family of five flying from Philadelphia, from March 30 to April 3, 2027. ChatGPT came in cheapest, suggesting about $8,500, but its hotel estimate was far too optimistic for those dates. Gemini estimated $10,050 to $13,350 after noticing the dates fall just before Easter Sunday 2027, in a busy spring-break period, and that kids 10 and older pay adult ticket prices. Perplexity's full estimate reached $10,545 to $13,955, more than $5,000 above ChatGPT's figure, and Caswell liked its itinerary best. Caswell judged that Gemini wins on budgeting. When shown the other two estimates, ChatGPT revised its target to about $10,000, with $11,000 available.

Check visa rules for a trip to Puerto Rico with ChatGPT and miss the flight

Spanish influencer Mery Caldass asked ChatGPT whether a visa was needed to fly to Puerto Rico and says the answer was no. That was true as far as it went, since EU citizens staying fewer than 90 days don't need a visa, but travelers still must complete the Electronic System for Travel Authorization (ESTA) to enter the United States. Without the travel authorization, Caldass missed the flight and posted a tearful TikTok video saying, 'That's what I get for not getting more information.' The trip wasn't ruined for long: the next day Caldass shared videos from a Bad Bunny concert in Puerto Rico.

Win hotel and airline refunds after a medical trip cancellation with ChatGPT

A Reddit user had to cancel a trip to Medellín, Colombia, at the last minute because of a sudden medical emergency, and the hotel and airline both refused refunds. The traveler told ChatGPT about a generalized anxiety disorder diagnosis backed by a doctor's note, and it read the policies of the airline, the hotel and Expedia and drafted a refund letter. The hotel agreed to a refund. The airline said it only refunded 'due to death or terminal illness', so ChatGPT wrote a second letter on how the condition affected flying, and an hour after it was sent, the airline changed its mind. The traveler says ChatGPT saved about $2,500.

Plan a five-country family trip with Gemini, despite some wrong tips (partial)

Manish Kurse planned a family trip through France, Germany, Luxembourg, Belgium and the Netherlands with little kids and several families, testing Gemini and ChatGPT along the way. A detailed prompt in Gemini Canvas, covering needs like vegetarian food and kids in strollers, produced a day-by-day itinerary that saved hours and was updated as plans changed. On the road, the AI helped with a lost parking ticket at an Amsterdam P+R, Brussels metro tickets and questions at the Louvre. But a highly recommended Paris creperie was closed, a pizza tip 'didn't sell pizza', and a chairlift in Cochem was shut. Google Maps mostly had it right; 'even Gemini gave the wrong answers.'

Check how long you can stay in a country visa-free, after ChatGPT gave the wrong limit (failure)

Samantha Miasnik, a Kazakhstan citizen living in Armenia, asked ChatGPT how long they could stay. ChatGPT said six months; the limit was three, which Miasnik found out too late. By then they had overstayed by three months and had to plan a visa run to Georgia and back, with a risk of being refused re-entry because of the overstay.

Get a $500 trip delay claim paid without receipts with a letter drafted by ChatGPT

Michelle got home 24 hours late after a snowstorm delayed a connection in Dallas: a night with friends, another full day at the airport, and a rerouted flight to a city about two hours from home. A Chase Sapphire Reserve card turned out to include trip delay insurance, but the claim wanted receipts and Michelle had none. Michelle told ChatGPT exactly what happened; it said the claim was worth a try, helped write a letter explaining everything, said to include the boarding pass and flight details, and showed where to submit it. A week later the claim was approved for $500, the maximum benefit, and the check arrived.

Plan a four-day family trip to London with ChatGPT, then have hotel concierges catch what it got wrong (partial)

Carley Thornell, a working parent, spent a few hours going back and forth with ChatGPT to plan a four-day London trip with their 6-year-old, ending up with a spreadsheet itinerary. On the ground, hotel concierges caught what it missed: a V&A exhibit sold out since day one with no walk-ups, a way into the British Museum's Egypt wing when general tickets were gone, a nut-free restaurant pick (Ping Pong) that had closed the previous year despite a 'permanently closed' flag on Google, and suggested bus routes 11 and 15 that don't go to the Science Museum or Hamleys. A rail strike the week they were there wasn't something ChatGPT could know. Some of its dining picks still worked out for the family.

Plan a sunset hike from a ChatGPT itinerary and get stuck at the summit after the last ropeway had gone (failure)

Dana Yao and their spouse used ChatGPT to plan a romantic hike up Mount Misen on Japan's Itsukushima island. They set off at 15:00 to reach the summit for sunset, exactly as ChatGPT had told them. ChatGPT said the last ropeway down was at 17:30, but when they got to the station to descend, the ropeway had already closed, and they were stuck at the top of the mountain.

Plan a six-day Oregon trip day by day with ChatGPT and Google Maps

The poster booked flights and Airbnbs, then for each day gave ChatGPT the start and end Airbnb, the kind of places they like and how much walking they were up for, and asked what to see along the route. They checked every suggestion on Google Maps, asked for hidden spots, then asked whether each day was feasible and what they'd missed, which turned up a redwood trail. Planning took about four hours; the poster says the plan worked almost perfectly without feeling rushed.

Win a Lufthansa refund for a cancelled trip over months of ChatGPT-written emails

After a Lisbon–Frankfurt–Miami flight was delayed, boarded and then cancelled, the poster gave up the trip and flew elsewhere. Lufthansa tried to charge for the Lisbon–Frankfurt leg and offered only 'the difference'. The poster fought it entirely by email using ChatGPT, and after months and a long chain of emails got the refund. They still lost money, days and the trip with their mother.

Draft a 13-day cross-country motorcycle route with Grok and ChatGPT, then catch a badly wrong route map

Planning a 13-day cross-country motorcycle ride for a year ahead, the poster asked Grok and ChatGPT for an initial route and itinerary. Grok's itinerary was 'a little wonky'; ChatGPT's schedule and route looked great. But when asked to draw a map of the route it had described, ChatGPT produced one that the poster says gets worse the more you look at it, making them question whether the itinerary itself was accurate.

Avoid the wrong travel insurance for a student abroad with ChatGPT

The poster's son, a Canadian studying in the U.S., was travelling overseas, and the poster almost bought travel insurance out of habit. ChatGPT pointed out the key issue: for this cover, residency mattered more than citizenship. They compared options and chose IMG Patriot International.

Plan a romantic, off-the-beaten-path Italy trip when you're too burned out to plan with ChatGPT

Burned out by work and a London heatwave, Santiago Barraza Lopez and their partner handed the planning to ChatGPT with one prompt and three rules: affordable, romantic, away from the tourist crowds. Its picks, all tied to a cheap flight into Salerno, were Salerno's old town, the fishing village of Cetara and Atrani in the shadow of Amalfi. Barraza Lopez says letting go of the planning brought calm and connection, and they came home feeling recalibrated.

Find off-the-radar stops along a 5,600 km road trip with ChatGPT o3

Planning a week-long road trip from Chicago to San Francisco via Alabama, Mississippi and Louisiana, the poster gave ChatGPT o3 a rough route, the things they wanted to see and questions in XML format, then refined the daily plans and switched part of the route. Asking 'is there anything to see between [x] and [y]' surfaced places they'd never heard of, including the Space and Rocket Center in Huntsville, Dauphin Island and its car ferry, and Saguaro and Guadalupe Mountains national parks, which they count among the best parts of the trip.

Get the lay of the land for a trip in half an hour and book a rental the same night with ChatGPT (partial)

Business Insider's Kelsey Vlamis usually spends hours reading about a destination before booking. For a Door County, Wisconsin trip, Vlamis asked ChatGPT which attractions people call overrated and which are worth the crowds, for timing tips, varied sample itineraries and which town suits someone who likes good food, nature, vintage shops and fewer crowds. In about half an hour Vlamis felt confident enough to book a waterside rental that same night. ChatGPT also recommended at least two restaurants that had closed years earlier.

Plan a Hong Kong trip with Gemini, Grok and ChatGPT (some addresses were made up)

A traveller planned a Hong Kong trip mainly with Gemini, using Grok and ChatGPT as extras, to organise locations, build itineraries, make packing lists and turn store addresses into Google Maps links. The traveller says routes were logical and personalised, but the AIs sometimes produced convincing addresses that didn't exist, and got names, opening hours or whether shops were still open wrong. Next time they'd verify every important detail on maps and official sites.

Build a calm, step-by-step Osaka trip guide for a neurodivergent traveller with ChatGPT

A traveller living with depression says ChatGPT helped them build a personal Osaka travel project: two books designed for them as a neurodivergent traveller, the second a field guide they planned to test in Osaka that September. They say it made the trip feel possible.

Ask ChatGPT whether a Schengen visa biometrics waiver applies, and miss the renewed-passport catch

A client applying for an Austrian Schengen visa asked ChatGPT whether biometrics were mandatory. It said they can be waived if you've had a Schengen visa in the last five years, allowing a third party to submit. Visa professional Chandan Pandey noticed the client's previous visa was in an old passport, and the waiver requires it to be in the current one. Pandey refused to submit it on the client's behalf; the client went for biometrics in person and confirmed the rule. Pandey says relying on ChatGPT's answer would have meant a rejected application.

Plan a 4-day family road trip to South Dakota with five chatbots and use the best plan

A Tom's Guide writer asked five chatbots to plan a four-day family trip from near Minneapolis to the Black Hills and Badlands, with gas and food stops, meals, lodging and under 1,400 miles in a borrowed minivan. Gemini was best at routing; ChatGPT did worst, with a broken map link and a needless night in the Badlands; Copilot was minimal; Claude was good apart from the route. DeepSeek won by basing the family in Custer State Park and planning every meal, and they followed its plan exactly, calling it a blast.

Untangle codeshare delay compensation across three jurisdictions with ChatGPT

When a delay turned a 2-hour layover into an overnight stay in Turkey, a traveller first used ChatGPT to translate their correspondence for a Turkish-only support portal, then got the runaround: two airlines, a codeshare, three jurisdictions, and compensation firms that turned them down. Once they explained the full situation, they say ChatGPT reasoned through the rules, told them which airline to chase and what to say, and that airline agreed to compensation; they say they got $500.

Plan a Tunisia trip with ChatGPT vs Claude, then travel the combined itinerary

A writer and their partner had ChatGPT and Claude each plan one day in Tunis, Tozeur and Hammamet, then built their trip from both. ChatGPT's plan was ambitious and cinematic; its Tozeur day 'nearly flattened' them with a far longer drive than implied, and a sandstorm blocked the road to the film sets. Claude's was slower and added two stops they loved, the Great Mosque of Kairouan and El Jem amphitheatre. They say ChatGPT delivered better memories and Claude more comfort and culture.

Plan a dog-friendly 7-day RV trip with short drives using ChatGPT

Planning an RV trip from Tampa with their partner and their dog, a poster asked ChatGPT for a 7-day route with no drive over 4 hours, waterfalls and short hikes, and dog-friendly stops. They also used it to check which state parks allow dogs on trails, how to connect a 30-amp RV to a 50-amp site, campfire cooking steps and campgrounds with cell service. They say it gave a day-by-day route with mileage and drive times, and dinner was saved.

Handle parking, road tolls and EV charging questions on a European road trip with ChatGPT and Grok

On a family road trip through Germany, Austria, Italy, Croatia and Slovenia, a poster used ChatGPT and Grok as an on-the-go assistant: planning village visits, walks and beaches, finding fairly-priced safe parking, choosing local beers and wines, and answering first-time EV road-trip questions such as where to buy national vignettes online, road taxes and trip-time estimates.

Make a personalized vacation packing checklist with a shared ChatGPT prompt

TechRadar's John-Anthony Disotto shares a long 'travel assistant' prompt (originally posted on Reddit) that asks for your age, destination and trip details, then builds a categorized packing checklist with clothing, tech, toiletries, luggage type and one commonly forgotten item. Trying it for their own trip, they say ChatGPT broke down their wardrobe into specific business-casual outfits, and that results are only as good as the details you give it.