Naperville’s size, wealth, accolades, and amenities make it a suburban behemoth outside of Chicago. Yet, when Naperville Magazine features in its current issue the story titled “Discover Hinsdale” (see the cover image below), it is a reversal of history regarding which community was more desirable.

Naperville was founded first in the early 1830s though Hinsdale was not far behind (and the community was originally known as Brush Hill and then Fullersburg). The two communities share a rail line in and out of Chicago, originally the Chicago, Burlington, & Quincy, which opened in the mid-1860s. While the two communities were similar in size until the postwar era, Hinsdale was the wealthier town. It had a hospital. It attracted executives as residents. It was at the eastern edge of DuPage County and just 15 miles from downtown Chicago. Naperville, in contrast, was seen more of a farm community, there wasn’t much development between it and Aurora (and little at all to the south or southwest), and it had lost some luster after losing the county seat to Wheaton in 1867.

Long-time Naperville resident and real estate agent described the relationship between the two suburbs in Is it Eden? Is it Camelot? It is Paradise? Better yet…It’s Naperville.

I discovered an overlooked “fact of life” one Saturday afternoon when a well-dressed, house-hunting couple entered our office. Both were quite disappointed to learn that our town had no tree-lined street full of gracious, period-type houses built in the 1920’s and 30’s, the likes of which they could find in some affluent suburbs east of us. They were also shocked to find we had so little “speculative” building and that our listings were generally of very old homes. The wife then made a biting comment that raised the hairs on my neck. She said, “Did you know that Naperville is rated a class ‘C’ town in some Hinsdale real estate offices?” “What in the world do you  mean!” I sputtered through clenched teeth. “Oh, don’t get made,” she replied, “Just in the area of ‘income per capita’.” “What in the world do you mean!” I sputtered through clenched teeth. “Oh, don’t get made,” she replied, “Just in the area of ‘income per capita’.” Well, Hal, I admit that I was truly deflated. Deflated because, even though it seemed such a minuscule area to me in light of all of Naperville’s ENDURING values, it was a fact of life, and there would be more people of this bent for us to deal with in the future. Hinsdale today is probably still the “class” community of the western suburbs. Time, effort and planning have earned it its reputation. Housing costs in Hinsdale are, on average, 30% higher than in Naperville. However, by now we must have about caught up in “income per capita”. I would (secretly) like to challenge Hinsdale to a rating battle based on “percent of residents with advanced college degrees.” Maybe then I might be able to walk into a realty office in their town and square a long-remembered rebuke by saying, “Did you know that in Naperville, some real estate offices rate Hinsdale a Class ‘B’ community?” I wonder if they’d squirm a little, as I did?” (“Dear Hal” column, Aug 28, 1981, The Naperville Sun)

A later story:

For as long as I can recall, having a Hinsdale (Ill.) residence address had the same effect on others as did the car, wristwatch, or college on attended – it “made a statement.” Aesthetic Hinsdale, with a population of only 17,000, has the highest income per capita of any community in DuPage County… ((“Dear Hal” column, May 17, 1981, The Naperville Sun)

The Naperville Magazine piece is similar to many you can find in suburban magazines. Here is the primary text that then leads to a list of attractions:

Just about halfway between Naperville and Chicago you’ll find the village of Hinsdale, known for its stop-and-stare-worthy homes along tree-shaded streets and a cute, compact downtown lined with shops and restaurants. Though the abundance of women’s clothing boutiques and pampering salons make it a popular destination for a ladies’ day out—no question—there’s a little bit of something for everyone in Hinsdale.

Hinsdale is now the quaint and wealthy suburb to visit. There are upscale restaurants and shops to explore as well as a few historical sites. The community is still wealthy and on average has higher incomes and housing values than Naperville. The teardown phenomenon seems to have begun earlier in Hinsdale in the 1980s before spreading to Naperville (according to several late-1980s columns by Herb Matter). Local celebrities seem to live more in Hinsdale than Naperville.

Yet, Naperville is the more vibrant place. It is clearly bigger. The downtown is more lively. Hinsdale is older money, Naperville more emblematic of the late-twentieth boom among the white-collar and educated.