Ask a child to name the most annoying things adults do for fun, and “drive around looking at houses” might top the list.

“We’re just looking around,” Mom or Dad would say.

Then I’d take her out for a drive around Chicago’s affluent north suburbs—Wilmette, Kenilworth, Winnetka, Glencoe, Highland Park, Lake Forest, and Lake Bluff—which offer a fascinating sampler of residential architecture of the late 19th and 20th centuries: Italian-style villas, French chateaus, and American takes on English country houses designed by the likes of David Adler, Arthur Heun, and Howard Van Doren Shaw; Prairie-style homes by Frank Lloyd Wright and his contemporaries (John Van Bergen, Dwight H. Perkins); and midcentury-modern marvels by architects such as Edward Dart, Keck & Keck, and A. James Speyer. She would act bored when I explained how North Shore real estate reflects both conservatism—initially drawing wealthy clients who preferred well-established, often European, architectural styles—and more forward-thinking design, with several Chicago architects treating it as a laboratory of sorts, a place to work out new ideas. Both of us would enjoy ogling the mind-blowing mansions overlooking Lake Michigan, the sprawling modern ranches perched on the edges of ravines, and of course the redbrick Georgian from Home Alone in Winnetka, where we’d stop for a selfie, both making the Kevin McCallister aftershave-sting face.

House gazing, whether on the North Shore or elsewhere, isn’t just one of the most stereotypically adult things I do now; it’s also, for better or worse, one of the most American Dream-like. The dream is always the same: When I make enough money, I tell myself, I’ll buy a place here or somewhere like it, a home with character, though, not a McMansion, preferably near a quaint train stop. The dream is also naive: I don’t give a lot of thought to where or how I’ll rake in my riches; it’s more like a game of MASH where one day I’ll just sort of arrive at “mansion” instead of “apartment” because that’s how things work out.