Success Quote by Jerry Della Femina

There is a whole civic inferiority complex packed into that casual jab. Jerry Della Femina, an ad man with a talent for turning contempt into copy, isn’t really reviewing Chicago so much as demonstrating advertising’s favorite move: downgrade reality, then sell the upgrade. The line flatters the speaker’s world-view that perception is pliable and that cities, like products, can be repositioned with enough nerve and budget. “That’s great advertising” lands as both compliment and insult: praise for the craft, sneer at the underlying premise that Chicago needs to be made desirable rather than simply lived in.

The “more than three hours” detail is the knife twist. It evokes the business traveler’s itinerary - fly in, meeting, steak, fly out - and implies Chicago’s natural setting is in the margins of someone else’s life. Della Femina isn’t just being coastal (though there’s plenty of that); he’s capturing a mid-century media hierarchy where New York is the default “real” city and everywhere else must earn screen time. Chicago becomes a case study in second-city anxiety, a place that supposedly requires advertising to compete with the gravitational pull of Manhattan narratives.

What makes the line work is its cynicism about culture itself: the idea that urban charisma is not discovered but manufactured. It’s an almost accidental confession from the advertising industry: if you can make people want to linger, you can make them want anything.