The First Answer Engine Built for Frequent Flyers

Every frequent flyer has run the same errand. You want to know whether it’s still worth chasing IHG Diamond, or why an airline suddenly rewrote its award chart, and you open a browser tab. Then another. Then five more. Somewhere in the mix is a post from 2019 that no longer applies, a forum thread with the right answer buried on page nine, and a comparison chart with a footnote you’ll never find again.

Randy Petersen has watched travelers run that errand for forty years. This spring, the founder of BoardingArea and FlyerTalk decided to end it.

Milepoint, which launched publicly in April, is the first answer engine built specifically for frequent flyers. Instead of a search box, it opens with a prompt. Ask it, in plain English, “How can I get IHG Diamond status?” or “Why do airlines change their rewards programs?” and it answers in a few sentences — no ten blue links, no cookie banners, no scrolling past someone else’s life story to find the point.

An AI trained on the people who actually know

What separates Milepoint from a general-purpose chatbot is what it has read. Developed in collaboration with ProRata.ai, Milepoint is trained exclusively on BoardingArea’s original content — the work of the independent bloggers who have covered miles, points, and loyalty for decades. When it answers a question, it isn’t guessing from the open internet. It’s summarizing a body of reporting the frequent flyer community already trusts.

Every answer arrives with sentence-level citations linking back to the source articles. Readers who want the two-sentence answer get it. Readers who want to dig into the reasoning behind a devaluation, or read the original post on a new elite benefit, are one click away from the writer who broke it.

That distinction matters more than it might sound. The dominant story of AI in publishing has been extraction — models trained on other people’s work with no path back to the source. Milepoint is a small, deliberate counter-argument: an AI that strengthens the writers whose work it depends on.

“Content creators such as Milepoint shouldn’t have to choose between reach and control,” says Annelies Jansen, Chief Business Officer at ProRata. “Gist Answers, our custom-built tool, lets Milepoint enhance their own content without sacrificing editorial integrity or losing readers to search engines operating without attribution.”

How it feels to use

Under the hood, Milepoint does a handful of things well. Answers are fact-based and grounded in BoardingArea reporting. Every response includes citations and further reading. The interaction is conversational, so a follow-up question — “What about spending on a co-brand card?” — gets a follow-up answer, not a fresh search. Over time, Milepoint learns what a given reader cares about and starts to surface the answers that matter to them.

Those aren’t hypothetical features. Milepoint spent months in beta with thousands of daily users before it opened to the public. The team combines the model with a human editorial touch — curating content, monitoring conversations, and tuning responses — so the tool improves the way any good publication does: with editors in the loop.

Why “asking” replaces “searching”

“The future of travel search isn’t search at all — it’s asking,” Petersen says. It’s a sharper claim than it first appears. Search rewards people who already know the right keywords. Asking rewards curiosity. For a frequent flyer trying to make sense of a program they’ve never used before, that shift is the whole game.

Milepoint is free, which is the other half of the argument. It gives travelers customized information for their specific needs and gives BoardingArea’s bloggers a new way to reach engaged readers — readers who arrive already looking for the exact answer their post provides.

Forty years in, the company that helped invent frequent flyer publishing is quietly rewriting the way it’s consumed. The search box was always a compromise. Milepoint just made it obvious.

Learn more at milepoint.com