Introduction

Origins of the Vintage Chicago History Project. 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 family and working life — vacations, 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 online public sources old Chicago photographs, postcards, lithographs, maps, and artwork, and then adding them to my photo archive after geotagging and captioning them. By 2025, I had a substantial, well-organized collection of vintage Chicago pictures and absolutely no way for anyone else to see them.

The arrival in 2025 of artificial intelligence platforms and one of its computer code-writing progeny, Anthropic’s Claude, helped me to create the interactive Vintage Chicago Map. By writing some 50,000 lines of code gobbledygook that I couldn’t, the machine named Claude enabled me to give all those vintage photos a utilitarian home by making them widely available on the interactive map platform of Vintage Chicago, A Cliff Dweller’s History.

Vintage Chicago, A Cliff Dweller’s History of Chicago’s Six Eras. A critical corollary complementing the interactive map’s visual focus on Chicago’s past is this companion textual narrative, A Cliff Dweller’s History of Chicago. A copy can also be accessed from the map’s legend. This brief history of Chicago has six chapters divided into the city’s chronological eras of the development:

1688–1812 Colonial Era. Chicago’s Native and colonial beginnings;
1813–1870 Early Settlement Era. Its early settlement and the arrival of the railroads;
1871–1900 Post-Fire Era. The Great Chicago Fire and the later rebuilding and industrial boom;
1901–1950 Jazz Age Era. The Great Migration and the Chicago Renaissance;
1950–2000 Digital Era. The second half of the twentieth century; and
2001–Present Contemporary Era. 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.

The Vintage Chicago Map Legend. The map’s legend is the Jane Byrne Interchange of the visual side of Vintage Chicago. You can get everywhere and access everything from it. Its numerous filters and era choices now open the door to more than 3,000 photographs that cover Chicago’s visual record from 1688, when the Italian Franciscan friar Vincenzo Coronelli drew the first printed map to carry the name “Chekagou,” down to today. Layered onto the map are galleries for 100 Famous Buildings and 50 Famous Architects, Famous Writer Locations, a filter for exploring each of Chicago’s 78 neighborhoods, aerial photos, historic maps and artwork.

The map legend has been designed to offer a variety of ways to view Chicago’s history. You can zoom down to a neighborhood street corner, take a closer at one of the city’s famous buildings or read about how the city evolved from a muddy trading post into 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.

The Cliff Dwellers. There is also a filter devoted to notable architects, writers, artists, and photographers of The Cliff Dwellers, the small downtown arts club that 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 members who have left their mark on Chicago’s cultural plane following the club’s founding in 1907.

Interest in Chicago History. 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.

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.

Interest in Chicago Architecture. 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.

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. These buildings included the Glessner House, and the Rookery. He was also centrally involved in the high-profile, and ultimately unsuccessful, battle to save Louis Sullivan’s Garrick Theater. (See The Demolition of Louis Sullivan’s Garrick Theater).

Acknowledgements. 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 of Chicago, the Newberry Library, the Chicago History Museum, the University of Chicago Library, the University of Illinois Chicago Library, the Chicago Architecture Center, the Chicagology resource, and Erik Nordstrom, with his architectural scholarship and his Building 51 museum and gallery.

Not to be forgotten are 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, as the Vintage Chicago map arrived well after most individual photo credits that once existed had been lost. I didn’t see the AI-assisted future coming far enough in advance to capture earlier available provenance.

Errors and Assigning Blame. This map and its history I’m sure have their quotient of gaps, misstatements, and errors. This may be particularly true where I was trying to assign an accurate geotag location to a map or the place from which an aerial photo was taken. If you stumble across other embarrassments, such as coding bugs or generative text that’s garbled, leave Claude out of it and blame me. I’ll deal with Claude myself if necessary.