More in Trip planning & itineraries. Also fits: Flights & trains.
Plan a week in Japan on 200,000 credit card points with ChatGPT and Gemini
Copy the prompt below and paste it into the AI tool named on this page.
Prompt Improved prompt
Our fuller version of the source's prompt, or one written to avoid a problem in the source. Not tested by the poster. It doesn't change what happened in the source.
Before you start, ask me 1–3 short questions about the details below and wait for my answers. Once I've answered, confirm the plan in one line and run the whole task start to finish. Goal: Plan a points-and-cash trip and show me exactly which points moves to make, flagging anything I must verify before transferring. Questions to ask me first: - Where, when and for how many travelers? - Which points programs and balances do you have, and how much cash? - Do you care more about cabin class, hotel quality or saving points? Inputs (fill in or confirm): - Destination, dates and travelers: [TRIP] - Points balances by program: [POINTS] - Cash budget: [CASH] - Priorities: [PRIORITIES] Rules: - List only transfer partners you can confirm on the card issuer's current partner page, with the link. - Give award prices as of today with a source and date, and say if a chart changed recently. - Include award taxes and fees for each option. - Never assume award seats are available; tell me where and how to search for them. Checkpoint: Show me the itinerary and the points plan, and stop before I transfer any points. If you get stuck: If you can't confirm a partner, price or fee, mark it 'verify' instead of guessing. Verify before you finish: Check that the points and cash totals add up and stay within my balances and budget. Output: A day-by-day plan, a points-and-cash table and a checklist of what to verify before transferring points. Done when: I have a plan where every transfer and price has been checked against current sources.
Customize this prompt
Answer these questions and we'll put your answers into the prompt for you. You can leave any of them empty.
Your prompt
Before you start, ask me 1–3 short questions about the details below and wait for my answers. Once I've answered, confirm the plan in one line and run the whole task start to finish. Goal: Plan a points-and-cash trip and show me exactly which points moves to make, flagging anything I must verify before transferring. Questions to ask me first: - Where, when and for how many travelers? - Which points programs and balances do you have, and how much cash? - Do you care more about cabin class, hotel quality or saving points? Inputs (fill in or confirm): - Destination, dates and travelers: [TRIP] - Points balances by program: [POINTS] - Cash budget: [CASH] - Priorities: [PRIORITIES] Rules: - List only transfer partners you can confirm on the card issuer's current partner page, with the link. - Give award prices as of today with a source and date, and say if a chart changed recently. - Include award taxes and fees for each option. - Never assume award seats are available; tell me where and how to search for them. Checkpoint: Show me the itinerary and the points plan, and stop before I transfer any points. If you get stuck: If you can't confirm a partner, price or fee, mark it 'verify' instead of guessing. Verify before you finish: Check that the points and cash totals add up and stay within my balances and budget. Output: A day-by-day plan, a points-and-cash table and a checklist of what to verify before transferring points. Done when: I have a plan where every transfer and price has been checked against current sources.
Scroll to see the whole prompt. Your answers show in green.
4 blanks are still empty: Destination, dates and travelers; Points balances by program; Cash budget; Priorities. They'll stay in brackets in your prompt, so the chat tool may ask you about them.
What you type stays in this browser tab. We don't send it or save it, and it's gone when you leave the page. If you use a "Try this in" button, your answers go to that tool as part of the prompt.
Try this in:
This prompt has blanks to fill in, like [TRIP]. We'll copy it instead of filling it in, so you can edit it before you send.
Opens in a new tab. We don't see what you send.
These links are only a shortcut. We're not affiliated with OpenAI, Google or xAI, and your results may not match the source.
The prompt they actually used
The exact prompt from the source.
Plan a one-week trip to Japan for two people in October 2026. We want to visit Tokyo and Kyoto. We have 200,000 Chase Ultimate Rewards points and a budget of $2,000 in cash for everything else. We want the best value possible.
AI tools
Outcome
Points traveler Jake Reeves gave ChatGPT, Gemini and Hilton's AI planner the same prompt: a one-week Tokyo and Kyoto trip for two in October 2026 using 200,000 Chase Ultimate Rewards points plus $2,000 in cash. All three produced a directionally correct itinerary, with the bullet train between cities and solid sights, and ChatGPT and Gemini both rightly suggested moving points to Hyatt for hotels. But ChatGPT said to transfer Chase points to ANA, which Chase doesn't partner with, and cited Hyatt Regency Kyoto at 15,000 points a night when the current rate is 17,000–23,000. Gemini pushed the Chase travel portal using an outdated rate, and none checked award seat availability or counted award taxes and fees. Reeves estimated AI can plan about 60 percent of a trip well.
Evidence: Article or interviewA newsletter, journalist or interview account of what happened.
Known limitations
PartialThe source says it only partly worked, or had a significant problem a person had to deal with.
What went wrong: The itinerary was sound, but the points advice had a made-up transfer partner, outdated prices and ignored fees and seat availability.
Source
- Posted
- by Jake Reeves (Platinum Flyer)
- Last checked
- Method:
- How we verify
https://platinumflyer.com/ai-plan-entire-trip-what-happened/
Context: Platinum Flyer is a points and credit card blog. Award charts and transfer partners change often, so verify them before moving any points.
More in Trip planning & itineraries
Plan a 'Goonies'-themed Pacific Northwest road trip with ChatGPT
Boston Globe columnist Meredith Goldstein asked ChatGPT to plan a trip from Portland, Oregon, to Seattle with a stop at Olympic National Park, built around filming sites from 'The Goonies.' It produced an itinerary and a list of 'Goonies' sites, but it agreed with every request: Day 1 left little time to pick up a rental car, it added multiple waterfalls, then a Willamette Valley winery, then Thor's Well when Goldstein asked what else not to miss. It also scheduled five other things on the Hoh Rain Forest day. Goldstein stopped revising and turned to people instead: a coworker said to give the Hoh a whole day and pointed out that Sequim is the lavender capital of the country, and Reddit advice to arrive at the Hoh by 7 a.m. meant no wait in line.
TravelTrip planningChatGPTPartialRecreated promptEvidence: Article or interviewView CaseCompare 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.
TravelTrip planningChatGPTGeminiPerplexityWorkedEvidence: Article or interviewBeginner-friendlyView CasePlan three family days in Paris, with ticket links, using Copilot
Paolo Asnaghi planned three August days in Paris for two adults and an 11-year-old, using only Copilot (with GPT-5). Asnaghi asked what to see from the hotel's area, excluding Disneyland, then asked for links to buy tickets in advance next to each description. Copilot grouped sights to avoid crossing the city, showed approximate prices and suggested a 3-day transit pass instead of single tickets. In about half an hour Asnaghi had a customized guide. The PDF it made wasn't user-friendly, though. During the trip, Copilot helped find places to eat, explained sights from photos and checked the weather for the next day's plans.
TravelTrip planningCopilotWorkedImproved promptEvidence: Described by posterBeginner-friendlyView CasePlan 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.'
TravelTrip planningGeminiChatGPTPartialRecreated promptEvidence: Described by posterView CaseBook a trip, flight, hotel and shuttle with ChatGPT Dots, and keep confirming the same booking (partial)
neom spent two hours trying ChatGPT's Dots agent and grades it B-. Asked to figure out a trip, it did; neom booked the flight and hotel, and Dots noticed the shuttle hadn't been booked and offered to book it with the details they'd discussed. But after neom said yes, it went back to the site, re-checked the details, asked for confirmation, filled in the booking form and then asked again whether to book. It can sign in with passwords, but wouldn't fetch two-factor codes from email even with email access, and its permissions checker rejected broad rules neom wrote, such as proceeding with routine, reversible actions without asking. neom finds it faster to use regular chat.
TravelTrip planningChatGPT DotsPartialRecreated promptEvidence: Described by posterView CaseGet real flight and hotel prices from a Claude Code travel skill, which only guessed price ranges until it was given a browser (partial)
Christopher Johnson built a Claude Code skill in about twenty minutes to act as a travel agent, sorting flights and places to stay for a business trip. Asked for real prices, it gave ranges, such as 'Flights typically run $280 to $420', and none of them was a price they could actually pay. Claude explained that the booking sites load prices with JavaScript after the page renders, which its tools couldn't see, so it had been estimating. With the Claude in Chrome extension installed and the same skill and request, it opened the sites and returned three specific places to stay with current prices and direct links. It was slower and used more of the plan's usage limits. They kept 'Act without asking' off, and Claude never bought anything.
TravelTrip planningClaude CodeClaude in ChromePartialRecreated promptEvidence: Described by posterView Case
Related cases
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.
TravelTrip planningChatGPTGeminiPerplexityWorkedEvidence: Article or interviewBeginner-friendlyView CasePlan 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.'
TravelTrip planningGeminiChatGPTPartialRecreated promptEvidence: Described by posterView CasePlan 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.
TravelTrip planningGeminiGrokChatGPTPartialRecreated promptEvidence: Described by posterView Case