How Smart Are Airlines With Upselling?

Skift Take
We're often told that travel brands will soon know what we want to buy before we do. But few airlines are anywhere near that level.
Almost every time I log into my United Airlines account to check an upcoming trip, I'm offered a special bundle with lounge access and a checked bag. It's priced at $72 for one of my next itineraries, from Newark to Dallas/Fort Worth.
I'm always amused. I'm a member of the United Club, so I don't need lounge access. I'm also an elite-level United frequent flyer, and receive checked bags for free, not that I have checked a bag in my decade taking business trips. Doesn't United know this?
I bring this up because my colleague Sean O'Neill, Skift's travel tech editor, has written a piece called Travel Upselling Gets Smarter Than Ever. It's one of 12 Megatrends Skift's team has identified for 2019.
He's right. Each year, brands become more sophisticated, and many have improved at how they send offers. O'Neill writes about how Finnair's chatbot can suggest tours and activities, and how more airlines are displaying visual representations of their ancillary products, which could make them attractive to customers. From experience, I know United has impressive functionality for upgrade upsells, often making a compelling offer just when I want to buy, such as when I'm on my way to the airport.
But for all the talk about how brands are leveraging data to personalize experiences for customers, I'm often surprise