How We Flew a Family of 5 to Hawaii
for $0 in airfare

Every summer my family takes one big trip. Five of us — my wife, our three kids, and me. And in 15 years of doing this, I've never paid cash for the flights. Not once. This is the full breakdown of this year's trip to Hawaii: exactly where the points came from, how I booked five seats on the same plane, and the cash price we never paid.

The trip — and what it should have cost

Salt Lake City to Honolulu, round trip, in June — peak season. When I priced the flights in cash, the total for five seats came to $4,850. That's a number that makes most families either shrink the trip or skip it.

We paid the taxes and fees — about $56 for the whole family — and that was it. The rest was points my business spending had already earned. No hacks, no gray areas, nothing you couldn't do with the spend you already have.

Where the 212,500 points came from

Here's the part most blogs skip: the points didn't come from churning 12 cards. They came from routing normal business spend through the right two cards for about 14 months.

• Materials and supplier runs went on a business card earning a flat 2x on everything — lumber yards and supply houses don't code as a bonus category anywhere, so flat-rate wins.
• Fuel, dining, and travel went on a card with 3x on those categories.
• One sign-up bonus — a single well-timed application before a big materials order — added 90,000 points in one shot.

That's it. Two cards, one bonus, normal spending. The points landed as flexible bank points, which matters for the next step.

The booking, step by step

Five award seats on one plane is the hard part. Airlines release award space in dribs — two seats here, three there. Here's the sequence that got us all on the same flight:

1. I searched 11 months out, the day the schedule opened. Family award booking rewards the early and punishes the casual.
2. I checked the airline's partner site first, not the airline itself. Partner sites often show saver space the airline's own search buries.
3. I found 42,500 points per person round trip — a fair rate for peak-season Hawaii, not a unicorn. 42,500 × 5 = 212,500.
4. I transferred points only after confirming seats. This is the rule I drill into every client: never move points to an airline until the award space is on your screen. Transfers are one-way.
5. I booked all five in one reservation, then called to link the kids' seats to ours. Twenty minutes on hold, done.

The rule that saves people the most grief: confirm the award space first, transfer the points second. Never the other way around.

The hotel side: 5 nights on points

Flights get the headlines, but hotels are where families quietly bleed cash. We used hotel points for a 5-night stay — a property where a standard room fit all five of us, which is its own skill in points travel (most award rooms cap at four guests; always check occupancy rules before you transfer anything).

Cash price for the stay: about $2,700. What we paid: points plus a $0 balance at checkout. Between flights and hotel, this was a $7,500+ trip for under $60 out of pocket.

How to run this play yourself

You don't need my exact cards or my exact route. You need three things: spend routed onto the right 2–3 cards for your situation, points kept flexible until you're ready to book, and an early, patient award search. That's the whole system. It's not complicated — it's just specific.

If you want the specific version for your spend and your dream trip, that's exactly what a Strategy Session is for. And if you just want to keep learning one move at a time, the free weekly email below is the place to start.