About
The Vintage Chicago map came about because there is truth in comedian Jerry Seinfeld’s observation, “Take your obsessive-compulsive disorder and make it work for you.” I retired in 2014 with a hard drive containing more than 70,000 photographs and no plan for what to do with them. Most photos were the ordinary residue of a working life — business trips for United Press International and later Encyclopaedia Britannica, family visits here and in France — basically the accumulated clutter that comes from always having a camera at hand. After retirement, with even more time on my hands, I turned my attention to collecting from public sources online old Chicago photographs, postcards, lithographs, maps, and artwork, and then geotagging and captioning them. By 2025 I had a substantial, well-organized collection of vintage Chicago pictures and absolutely no way for anyone to see them but myself.
Wary that Seinfeld’s words might apply to me, I confronted this question: Was I really just a normal person with a photography hobby, or had I turned into a serial, shutter strutter in need of therapeutic advice from a non-licensed physician like Seinfeld? I began to fear people might be whispering behind my back in tones suggesting I was a hoarder, “Psst! You know, he collects old photographs for no reason.” Afraid that I might be a nut and cracking up, I was rescued when I finally cracked the nut of what to do with all those gigabytes of historic Chicago photos laying fallow on my hard drive. My savior was the arrival in 2025 of AI and its code-writing progeny Anthropic’s Claude. By writing 50,000 lines of code gobbledygook that I couldn’t, Claude enabled me to give all those vintage photos a utilitarian home that made them widely available on the map platform of Vintage Chicago, A Cliff Dweller’s History.
This interactive map had more than 2,400 photographs at the outset. It has grown since then, and now covers Chicago’s visual record from the present back to Vincenzo Coronelli’s 1688 map, the first printed map to carry the name “Chekagou.” Layered onto the map are galleries for 100 Famous Buildings and 50 Famous Architects, 88 Famous Writer locations, a filter for exploring each of Chicago’s 78 neighborhoods, aerial photos and historic maps, and a set of pages devoted to notable architects, writers, artists, and photographers of The Cliff Dwellers, the small downtown arts club I’ve belonged to for decades and once served as president. This connection is why I refer to the Vintage Chicago map as “A Cliff Dweller’s History.” It’s a personal label as much as a descriptive one, and the map permits me to celebrate the role of some of the club’s architects, writers, artists, and photographers who have left their mark on Chicago’s cultural plane following the club’s founding in 1907.
The map legend has been designed to offer a variety of ways to view Chicago’s history. You can easily zoom into a neighborhood street corner or to one of the city’s famous buildings or read about how the city evolved from a muddy trading post to the global metropolis of today. You can also begin to understand how it was that Chicago arrived in its current role as the architectural design capital for distant megatall structures all over the world.
Complementing the map’s visual focus on Chicago’s past is a 25,000-word narrative, A Cliff Dweller’s History of Chicago, also accessed from the map’s legend. Its chapters cover six chronological eras: Chicago’s Native and colonial beginnings; early settlement and the arrival of the railroads; the Great Chicago Fire and the industrial boom; the Jazz Age; the second half of the twentieth century; and the city as it stands today. Each chapter is illustrated with historic photographs from the map and concludes with a hot linked bibliography to encourage further reading.
In this early period of AI adoption, you should be aware the Anthropic’s Claude platform was engaged beyond the computer code-writing function involved in creating the interactive map. It both followed my guidance in researching the particular historic issues I wanted to include in the narrative history of Chicago’s six eras of development, and then went on to generate the bulk of the text of the final narrative. Merriam-Webster, the premier dictionary of American English I briefly headed in the 1990s, declared “slop” (as in AI slop) as its 2025 Word of the Year. Merriam defined “slop” as now including, “digital content of low quality that is produced usually in quantity by means of artificial intelligence.” Formerly, “slop” was generally used to describe, “product of little value” or “food waste fed to animals.” I believe the text of Vintage Chicago’s historical narrative, which incorporates my personal subject matter guidance, independent research, and editorial engagement, has taken the resulting work well out of the realm of the “soulless AI slop” category increasingly prevalent these days, but that’s just my opinion. Check it out for yourself.
My original interest in Chicago history goes back to a single spring school vacation when I was a teenager. My mother, eager to keep me both educated and out from underfoot, suggested I spend some days at the Newberry Library, where a family connection — my cousin John Bowe’s wife was the daughter of the Newberry’s librarian back in the day, Stanley Pargellis. I imagine I must have asked the desk clerk whether they had anything on Chicago history that I might read. Did they ever. Before long I was poking through A. T. Andreas’s three-volume History of Chicago. This grand story of the city’s early history begins with LaSalle’s 1679 expedition, and carries through to the 1812 Fort Dearborn massacre, the Illinois and Michigan Canal, the railroads, the Great Fire of 1871, and Chicago’s immediate and astounding recovery right up to the year 1884, when Andreas published his first volume. I didn’t appreciate it fully at the time, but that week at a Newberry reading table set something afoot that took another 70 years or so to fully develop.
The Vintage Chicago map’s special focus on Chicago’s architectural history reflects a lifelong interest in architecture engendered by my uncle, my father’s brother Judge Augustine J. Bowe. Mayor Richard J. Daley had appointed him in 1957 as the first chairman of Chicago’s new Commission on Chicago Architectural Landmarks. Gus had been a prominent attorney and a past President of the Chicago Bar Association and Daley’s commission was established by a city ordinance passed that year, making it the first official municipal body in Chicago dedicated to identifying and preserving the city’s architectural heritage. The commission Gus headed was the direct precursor to today’s Commission on Chicago Landmarks, which was created under a stronger ordinance in 1968, two years after my uncle’s death in 1966. As the Commission’s inaugural chairman, Gus led it during its formative years, including the significant 1960 initiative that designated the first 38 buildings as official landmarks such as the Glessner House, in which I was once married, and the Rookery. He was also centrally involved in the high-profile, and ultimately unsuccessful, battle to save Louis Sullivan’s Garrick Theater. After 1960, Gus was also serving the city as its newly elected Chief Justice of the Municipal Court of Chicago. Gus was a poet as much as a jurist, and the evenings I spent with him while I was in law school amounted to a second education for me, not just in architecture, but in literature, politics, and the city’s past.
A work like the Vintage Chicago map would not exist without the institutions and people who do the difficult, patient work of keeping Chicago’s past alive for later generations. To name a few: the Ryerson and Burnham Library at the Art Institute, the Newberry Library, the Chicago History Museum, the University of Chicago Library, the Chicago Architecture Center, those who built the Chicagology resource, Erik Nordstrom’s architectural scholarship and his Building 51 museum and gallery, and the generous members of half a dozen Facebook Chicago history groups who kept turning up photographs I’d never have found on my own. I owe all of them a debt I can only repay in general terms, since the Vintage Chicago map arrived well after most individual photo credits that may have once existed had been lost to time. Sadly, I never saw the AI-assisted future coming far enough in advance to save earlier available provenance.
Today, I look back on the Vintage Chicago map with some satisfaction. While I’m still taking pictures like crazy, I think on my way to being cured of the incipient Seinfeldian obsessive-compulsive or paranoic tendencies triggered by the disease of collecting things you have no use for.
Like any project built by one person working mostly alone, this map and its history are bound to carry my own gaps, guesses, and outright errors. I’d rather you find them by exploring than have me pretend they don’t exist.
