A house in Wilmette Credit: April Alonso

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

When I was growing up, my parents would, without warning, take a meandering route home from the mall, church, or Sam’s Club to gawk at real estate on unfamiliar streets in previously unexplored neighborhoods of southwest Michigan.

In the backseat of the car, my siblings and I reacted to such detours as if we were literally dying of boredom. (Smartphones had not been invented yet, and we had no Neko Atsume virtual cats to feed.)


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

“But WHYYY?!”

“Because we’re curious.”

Ugh, the selfishness! The insouciance! My parents’ curiosity was robbing me of precious time I’d planned to, I dunno, watch Saved By the Bell or read a Judy Blume book or stare in the mirror and make poor choices about how to style my bangs.

Now I wish I could go back in time and inform that girl that in her 30s she’d love doing the very activity she and her siblings were losing their shit over: spending weekend afternoons just driving around, looking around. “House gazing,” I’d explain to my tween self. “It’s something I do because I’m curious, and curiosity is actually a really great quality of Mom and Dad’s, so get over yourself for one sec and just appreciate that they drive your ass everywhere. . . . Yes, I say ‘ass’ now. And since I have your ear, maybe ease up on the Rave Ultra Hold hairspray?”

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.

“OK, the Home Alone house was kind of cool,” 11-year-old me would tell 34-year-old me.

What would impress this girl about the North Shore is what impresses me now—at least when I don’t think too hard about things like unchecked privilege and cultural homogeneity and the wealth gap: It’s tree-lined and lake adjacent, with roads that casually curve and jog in marked contrast to the rigidity of Chicago’s streets. There are wide green lawns, quaint train stops, the summer-long Ravinia Festival, and postcard-perfect downtowns. Immortalized in a crop of some of the most iconic movies of the 1980s, it’s a place that makes me feel at once curious and nostalgic for somewhere I’ve never lived. There’s Cameron’s glass-and-steel house designed by Speyer (and the adjacent car showroom pavilion by David Haid) from Ferris Bueller’s Day Off (1986), the exterior of Joel’s house from Risky Business (1983), and the Jarretts’ estate in Ordinary People (1980)—all three located in Highland Park.

Despite my superficial familiarity with these elite pieces of property, they have always struck me as “other”: extravagant extensions of other lives in other tax brackets and other zip codes. Houses with wine cellars and movie theaters and tennis courts, whether or not their owners drink wine, watch movies, or play tennis.

The third of four children born to two public school educators, I grew up in a house that was comfortable but in no way North Shore palatial. Still, the aspirational young girl in me (the one who thought she had a decent chance of marrying Prince William, if only we could meet) and the real estate-obsessed adult (a freelance journalist whose bank account is all too frequently a real sad state of affairs) wonder what it would be like to live somewhere so idyllic. Who even owns these places, anyhow? And would they consider renting me the coach house?

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.

“Can you show me where Ferris Bueller lived?” the younger me would ask.

“That house is actually in Long Beach, California,” I’d tell her. And in the rearview mirror, I’d notice her bummed expression, as if I had just informed her she wasn’t going to marry Prince William. “How about instead we swing by Molly Ringwald’s house from Sixteen Candles?” v