8 prompts for points and miles that work in any AI assistant, with a version for ChatGPT, Claude, Gemini, Perplexity, Copilot and Meta Muse. They make the assistant do the real maths (fees, what cash earns, your card's transfer ratio) and tell you what to check before you transfer.
Pick your assistant
The prompts
They work anywhere. The assistant pages add how to connect Points or Cash and what to double-check.
Points or cash, decided
I'm looking at [route] in [cabin] on [date]. Cash is [price]. The award is [miles] [program] miles plus [taxes and fees]. Work out cents per point after the fees and after what the cash ticket would earn me, compare it with 1 to 1.5 cents as a normal good redemption, and tell me in one line: use points or pay cash.It forces the maths most people skip: fees come off the cash price, and a cash ticket earns miles you give up by redeeming.
Find the cheapest transfer path
I hold [balances, e.g. 120k Amex Membership Rewards, 40k Chase Ultimate Rewards]. My cards are issued in [country]. I want [the award, e.g. business class Brussels to New York]. List every way my points can reach a program that prices it, with the transfer ratio for my card's country, how many bank points each path costs, and which is cheapest.Transfer ratios differ by the card's country (a Belgian Amex is 2:1 to Flying Blue, a US one 1:1), so the issuing country changes the answer.
Shortlist the programs that price your route well
I'm flying from [home region] to [destination region] in [cabin], one way. Which loyalty programs usually price this well on saver awards, roughly how many miles each, and which ones add high fuel surcharges I should avoid?Asking for surcharges too stops the classic trap: a cheap-looking miles price with hundreds in fees on top.
The check before you move your points
Before I transfer [points] to [program] for [flight and date], give me a short checklist: how to confirm the seat is really bookable, the taxes I'll pay, how long the transfer takes, whether it can be undone, and what to do if the seat disappears.Transfers are one way. Checking the seat first is the one habit that saves people from stranded miles.
Plan your lounges for the whole trip
My trip is [airports in order], flying [airline and cabin], with [cards and airline status]. For each airport, list the lounges I can use, how I get in (ticket, status, card or Priority Pass), guest rules, and any that often turn Priority Pass members away.Lounge access depends on the ticket, the status and the card together, and card benefits change by issuing country.
Value what paying cash earns you
If I pay [price] cash with [card], what do I earn back in points, miles or cash back, what is that worth at a conservative 1 cent a point, and does it change whether I should use points instead?Cash back and card points are part of the cash option. Leaving them out makes points look better than they are.
Rescue miles before they expire
Here are my balances and the last time each one earned or spent: [list]. Which expire soonest, what is the cheapest way to keep each one alive, and is any balance worth topping up for an award I would actually take?Most miles survive with one small earn or spend. It's cheaper to keep a balance than to rebuild it.
A work trip: should you use your own points?
This trip is for work and [my company pays the fare / I run my own company]. Should I use my own points? What do I earn on the cash ticket, and what would the company earn if it joined [bluebiz / PartnerPlusBenefit / On Business]?When the company pays, the cash fare costs you nothing: keep your points and earn on the ticket. Company programs add a second earn on the same flight.
Questions
Which AI assistant is best for travel hacking?
The one that can use real data. ChatGPT and Claude can connect Points or Cash for transfer ratios and award prices; Perplexity is strong on recent news with sources; Gemini and Copilot are quick for cash fares. For any of them, give it your numbers and ask for the maths.
Can I trust the numbers an AI gives me?
Check them. Award prices and transfer ratios change, and assistants often quote US figures from old articles. Confirm the seat on the airline's site and the ratio for your card's country before you transfer points.
Do these prompts work in other assistants?
Yes. They are plain text: fill in the brackets and paste them anywhere.
Skip the prompting.
Mila already knows the ratios for your card's country, the award prices and the cash fare. Ask her the trip.
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