Using AI to find the smartest hotel booking

Reading Time: 3 min

For the longest time, I would decide if a points redemption for a hotel stay was “good” entirely by its cents-per-point value. If the math looked good, I booked it. If it didn’t, I’d usually pay cash and move on.

But over the past few months, I've started using AI to compare hotel bookings based on the way I actually travel — and it’s completely changed how I think about points.

Instead of just looking at the redemption rate, I now factor in location, resort fees, breakfast, parking, elite perks, and even how convenient the hotel actually is for my trip.

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A few weeks ago, I was pricing out a luxury Marriott stay in Naples, Florida, for a family trip where rates were hovering around $400 per night or 70,000 points per night. At first glance, redeeming points looked like the obvious move. But after running the numbers through AI, I started looking at the booking a little differently.

Marriott doesn't waive resort fees on award stays the way Hyatt and Hilton often do, so I'd still owe the $61 daily resort fee plus $40 per day for valet parking — which made redeeming points feel a lot less compelling.

What really made me rethink booking my hotel with points was that a Florida resident rate included two complimentary rounds of golf per day. Tee times at the resort started around $159 per person, and since my wife and I were planning to golf during the trip anyway, that was like getting more than $300 back in value per day on a roughly $400 nightly booking.

Once I looked at the stay from that perspective, rather than focusing only on the redemption math, paying cash turned out to be the smarter move — and it let me save my Marriott points for a future redemption that would deliver stronger value. Honestly, I probably wouldn’t have thought about it that way if I hadn’t run everything through AI first.

One thing I noticed pretty quickly is that this process doesn’t need to be complicated.

Most of the time, I’ll just paste the hotel name, cash rate, points rate, taxes, resort fees, and any perks tied to the booking into ChatGPT and ask something like:

I’m booking the following hotel. Using the information below, evaluate what’s the better deal for booking: using points or paying cash.

Hotel name: [ ]
Travel dates: [ ]
Cash rate: [ ]
Points rate: [ ]
Taxes: [ ]
Resort fees: [ ]
Any perks tied to the booking, like elite status or Amex Fine Hotels & Resorts perks: [ ]

In the previous Marriott example, I went into the search fully expecting to use points. But once I compared everything side by side in AI, it surfaced a Florida resident rate that included two complimentary rounds of golf per day — a package my wife and I almost definitely would’ve overlooked otherwise. Since we already planned to golf during the trip, that completely changed my value calculation.

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Other times, it helps me think through things like bonus-point promotions, free breakfast with hotel elite status, parking costs, or whether paying cash could help me requalify for status faster. I’ve even started using it to decide whether it makes more sense to burn a free night certificate now or save it for a much more expensive stay later in the year.

I still care about getting good value from my points, obviously. But now I’m looking at the full trip cost and overall experience instead of getting completely hung up on the redemption math alone.

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