Why United Pulled Me In
After dropping the American obsession, I started thinking about which airline actually made sense for my life. I moved to Chicago in 2022, and O’Hare is a United hub. Inertia did some of the work. But United earned more of it.
Earlier this year I tried United’s TSA PreCheck Touchless ID program at O’Hare — biometric screening that lets eligible flyers pass security and drop bags without ever pulling out a boarding pass or license. It was the kind of frictionless airport experience that makes you forget how bad airports usually are. That stuck with me.
The United app is also genuinely good. Live weather updates. Real-time flight countdowns. Features that solve actual problems instead of existing to look impressive in a press release. Between the technology, the O’Hare footprint, and the people I’ve gotten to know on the United team, this has become my default airline flying out of Chicago.
The Threshold Problem
The frustrating part? United keeps raising the bar. The miles you need. The segments. The spending. Every year the goalpost moves, and every year the airlines act surprised when frequent flyers feel cheated.
United isn’t alone in this. When Delta announced its SkyMiles overhaul in fall 2023, the backlash was loud enough to make national news. The loyalty programs that were built to reward loyalty are now designed primarily to extract spending. No airline is doing anything to persuade me that chasing their status is worth my time.
The Lounge Problem Nobody Talks About
The argument for status usually loops back to lounge access. Quiet seating. Free drinks. A place to decompress before a long flight. I understand the appeal.
But I have dietary restrictions, and most airport lounges don’t accommodate them. The food spread — the thing that’s supposed to justify arriving early — is largely useless to me.
So the calculus breaks down. If there’s no lounge food I can eat, there’s no reason to arrive early. If there’s no reason to arrive early, TSA PreCheck and Clear — which regularly get me through security in under five minutes — are all I actually need. I’d rather be at the gate for 20 minutes than in a lounge for 90.
Flying Like It’s Supposed to Feel
My actual strategy is simple: fly the airline with the best schedule for my route, at the best price. I prefer Midway over O’Hare because the traffic to O’Hare can burn an hour each way. That makes Southwest — which hubs at Midway — a frequent choice. When I’m flying out of O’Hare, I default to United. If American or Delta or Alaska has a cheaper or more convenient option, I take it.
No program shopping. No mileage math. No manufactured loyalty to an airline that’s already decided to make earning status harder every year anyway. The frequent flyer programs have gotten complicated to the point of absurdity, with too many earning paths and requirements that shift before most people can hit them.
Traveling is supposed to feel good. This is the one part of it I refuse to turn into homework.
