Let's Take a Day Trip

When I joined Reddit earlier this year, one line kept appearing in aviation threads: “If you want first class, then buy first.” I thought it was just people being snarky, usually said to travelers frustrated about not clearing an upgrade despite having elite status. Sometimes it came up when airlines sold discounted First Class seats instead of giving them away at the gate.

But during my most recent status run, that phrase finally clicked.

I was wrapping up a long day of flying—Chicago to Boston, Boston to San Diego, San Diego to Seattle—and still needed one more push to close my elite-mile gap. When I checked flights home, a First Class seat from Seattle to Chicago was going for $523. I already had a credit from a canceled flight, so I went for it.

It turned out to be the best decision of the entire trip.

The seat was comfortable, the meal was solid, and I lucked out with an empty seat next to me. On a four-hour overnight flight, extra space feels like a small gift. Somewhere between Washington and Montana, with a plate of short ribs beside me and a quiet cabin around me, I started wondering: Could I realistically do this more often next year?

Surprisingly, the answer was yes.

For long flights—anything around four hours or more—the difference in rest, comfort, and overall experience is huge. And when the fare is reasonable, buying First Class outright can actually make more financial sense than playing the upgrade lottery, especially for someone chasing Alaska Airlines status.

That’s because Alaska’s mileage rules reward paid premium cabins. A SEA–ORD flight earns about 1,700 miles normally, but in a First Class fare purchased through Alaska, that becomes roughly 2,500+ elite-qualifying miles because Alaska gives a 150–200% mileage bonus for paid First Class tickets. Even if the flight is operated by American, the Alaska booking triggers the Alaska earning chart. When you’re closing out the last few thousand miles before elite-year deadlines, those bonuses matter.

That was the difference between needing another weekend of flying and finishing everything in one trip.

And here’s the part many travelers don’t expect: reasonable First Class fares do exist. For me, “reasonable” means $550 or less for a one-way. Some may say that’s impossible, but it’s not. At the time of this writing, Chicago to San Juan in First Class is going for $493 on United. The same weekend, First Class from Chicago to Los Angeles is $394 on American. Both are 4.5-hour flights, and for that length of time, the comfort is worth it.

Of course, I wouldn’t buy First Class for every route. A hop to Memphis, Toronto, Minneapolis or Cleveland—anything around two hours—doesn’t justify the cost. With my status, I’d likely get upgraded anyway, and even if I didn’t, two hours goes by quickly.

But for 2026, the plan is simple: fly First Class when it makes sense. If the price is reasonable, if the flight is long, and if the mileage bonus helps me retain status, it’s a smart move. Travel is about experience, and for me, comfort matters. If I can step off a plane feeling rested and earn elite miles at the same time, that’s a win.

Reddit wasn’t wrong.
If you want First Class, then buy first.