
CBS – Southwest Airlines boasts that its passengers’ “bags fly free” — but not for long.
Starting May 28 — just in time for the busy summer travel season — only Southwest’s most elite Rapid Rewards A-List Preferred members and passengers who book their top-tier Business Select fares will receive two free checked bags. Frequent flyer A-List Members, Southwest-branded credit card holders and other select customers will be allowed one checked bag.
Everyone else will be charged for their first and second checked bags on flights booked on or after May 28, the carrier says.
It’s a break with Southwest’s 54 year history — one that could undermine customer loyalty to the carrier, according to experts.
No joke this could be one of the worst days in the history of my shit talking career. Honestly. Fuck me sideways.
I’ve been propped up by my love for Midway airport and the convenience of Southwest Airlines for so long that I’m quite literally numb to other airlines. I don’t care about your lounge or inflight entertainment or legroom or anything. Never paid attention to anyone else’s bullshit because Southwest was always on point, on time, customer friendly and bags flew free. It was a simple business model that made every golf trip, Vegas weekend, bachelor party that much easier to haul a ton of unnecessary shit around.
And now those days are over.
Some people like Doug Gladden are PISSED


And I don’t blame him because the customer loyalty just can’t be compromised.
People treat airlines in the highest tier of loyalty. Right there with Vegas casinos and fast casual dining options like Chilis and Hooters. Once you get an airline you like and you build that bond, you don’t want to go looking for a new one.
And a step further – airline loyalty is enough to start an argument with a stranger. Or my wife’s friends’ husbands, for example. You could hear something snobby about Delta and instantly say something like “Are you out of your fucking mind buddy?” and then people will be like WOAH YOU NEED TO CALM DOWN and I’ll be like “This guy doesn’t know shit about airlines and you’re telling me to cool it?!”
BAGS FLY FREE
Not anymore. And now I’m severely disadvantaged when it comes to defending Midway and by extension Southwest. Our greatest card by a mile has been turned in for the sake of profitability.
But then deep down I’m still compelled to believe in Southwest. Like I’m not throwing in the towel just yet. There’s gotta be a better explanation than just saving costs?
Personally I’m just never going to be a guy who pays extra-extra for Business Select anything. That’s such a huge reach for my own value structure. But assuming there’s deeper intentions, I like to think Southwest is challenging me to be more successful now so I can bootstrap myself into Business Select. They’re trying to give me the necessary motivation to advance myself out of the low cost airline herd. Maybe that’s the deeper explanation.
If you don’t like the class of consumer you identify with, change your class of consumer.
Probably the Southwest CEO
^^Greasy Bastard^^
My in-laws live by O’Hare and they watch the dog almost always when we travel. So I’ve grown accustomed to wearing the ball-gag and following her lead on United when we travel. And now with this news about the updated fees, there’s a small chance I go years without flying Southwest. Notwithstanding a significant discount or various atypical circumstances, I just don’t see it happening and that really fucking bothers me.
PS – My practical transition to O’Hare over the last couple years reminds me of when I realized I started smoking in 2021. Even though it had been a couple years of casually buying packs. It wasn’t until one day I realized that I had regularly bought cigarettes for so long that I was technically a smoker and that jarred me. I never thought that would happen. Ultimately I quit a few months after this realization but it still happened. I still became a smoker and that’s always going to be crazy to me to think about in hindsight.
That same feeling applies to my travel out of O’Hare. It’s not until you sit down and think about the Southwest bag policy that you realize most of your travel no longer originates from Midway. And to be quite honest guys, that’s a heavy realization for me.
Overall just a really sad turn of events.
PPS – United’s not that bad.