Before You Pay for an Upgrade, Check What You Already Own

Once you move credit card points into an airline's points scheme, you usually can't move them back.

Remember that at check-in, when you're half-packed and the airline offers you a better seat at a price that feels made up. Is it a good deal?

You've no idea, so you either pay or you don't. Meanwhile your points sit in three places that nobody adds up. Some are at the airline, some on a credit card and some in a hotel account you forgot about.

AI is good at the adding up, so do the sums the day you book. Then when the offer comes, you'll be ready.

Write down what you hold

Before you open any AI tool, spend five minutes writing a plain list, because you know your accounts better than any chatbot does.

• Your airline points balance and your status with the airline
• Credit card points, and which card they're on
• Vouchers, companion tickets and travel credit
• The flight itself, meaning the airline, date, route and the fare you paid

Leave out passwords, card numbers and your booking reference, because the maths doesn't need them.

Ask for today's rules, with a link for each

Upgrade rules change all the time, and AI will happily quote a rule that ended last year. So paste your list into ChatGPT or Claude with web search switched on, which lets the AI look things up online right now.

Here's what I hold and the flight I'm on. [paste your list]

Search the current rules for this airline's upgrades and for any of my points that can be converted to it. List every realistic way I could move up a cabin on this flight, including paying cash.

For each option, tell me what it would cost, whether it confirms a seat or just puts me on a waiting list, and a link to the rule you're relying on. Mark anything you're estimating. Don't recommend one yet.

The last line is there because it stops the AI pushing you towards one option before you've seen them all.

Then look closely at the links. The AI can't see your booking or which seats are free right now unless you show it, so it's working from your list and whatever it finds online.

An answer with no link to a current rule is a guess.

Work out what each point is worth

One sum turns a vague offer into a clear decision, so ask the AI to show its working.

For each option that uses points, divide the cash price of the same upgrade by the points it costs. Show me the value per point in pence, and the calculation.

As a made-up example, say an upgrade costs £150 in cash or 20,000 points, which makes each point worth 0.75p. Is that good?

That depends on what else those points could buy you, like a full holiday flight next year. Check at least one of the AI's calculations yourself.

Twenty thousand points is a number, but a week away with the kids in economy is a decision. So is one long flight with room to sleep, and only you know which your family would choose. Sometimes the best answer is to keep the points and sit in economy, and a good assistant will tell you that.

If yours never does, ask what you'd be giving up.

Don't move any card points until you've decided, because once they've moved, they usually stay moved.

Make the booking yourself

Book the option you chose on the airline's own app or website. You'll see the live price there, and the price may have changed since the AI looked.

Some AI tools can now click through websites for you. For example, Claude can do this in your browser with the Claude in Chrome extension, which is a small add-on for the Chrome browser. If you use one of these tools, tell it to stop before anything that spends money or points, and then press the last button yourself.