Vintage Chicago 1688–Present

About

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 Vintage Chicago interactive 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 textual narrative, A Cliff Dweller’s History of Chicago’s Six Eras, also accessed from the map’s legend. This short history of Chicago has six chapters divided into the chronological eras of the city’s 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;
• 1951–2000 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. To help you find what you’re interested in, there is a full Index at the end to consult.

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 to everything from it. Its numerous filters and era choices now access 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, Northwestern University Library, the University of Illinois Chicago Library, the Chicago Architecture Center, those who built 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.

Acknowledgements

Acknowledgement Limitations

Now that Vintage Chicago is built, it’s too late to go back and retrieve the information as to where many of these photos found on the internet came from and credit the proper parties for posting them. I simply didn’t foresee that my personal collection of old Chicago photos might one day take flight from my hard drive to a vehicle such as the Vintage Chicago map. Had I been more of a seer, I would have taken care in trying to save the provenance of the map’s photos when it was occasionally available. But, I never saw AI coming around the corner at us.

Creating Vintage Chicago

Say hello to Anthropic’s Claude, a 2025 poseur presenting himself as my new python vibe coding buddy. Never in my life had I ever had the remotest interest in learning how to write code for a computer. However, as I began experimenting with the early free AI platforms, I found that I could vicariously code if I politely “chatted” with Claude, asked right questions, and then worked with the AI platform to fix my inelegant prompts and Claude’s inevitable script bugs.

My hope was that if I could finally create an interactive map populated with the photos that I had carefully captioned and geotagged, I would have built something of interest to others as well as myself.

It turned out the biggest problem in bringing the Vintage Chicago map to fruition was the design and execution of the map’s legend. The legend has more than a dozen major filters and hundreds of sub filter combinations, and it was quite a trick to finally create a reasonably navigable tableau instead of the visual mishmash I started with.

Time for Acknowledgements

Fortunately, it’s not too late to thank and acknowledge in a general way those people and institutions that helped put these images in front of me. While individual photo creators may be hard to acknowledge at this time, it remains easy and important to call out and hail the most important parent sources of many of the photos on the Vintage Chicago Map.

Erik Nordstrom

An entrepreneur following his heart, a premier scholar, a cataloger of much of Chicago’s important and disappearing architectural history, and an appreciator, like myself, of the dynamic trio of architectural preservationists Richard Nickel, John Vinci, and Tim Samuelson, Erik has served Chicago, and its cultural curators well. He regularly credits the Ryerson and Burnham Library of the Art Institute of Chicago, the Newberry Library, the Chicago History Museum, as well as his own “Courtesy of Building 51” business in architectural artifacts.

Facebook Chicago Groups

Many photos on the map got there because of my seeing them first on Meta’s Facebook app. It turns out there are lots of lovers of old Chicago with both old and new photos to share. Who grew up where? What neighborhood childhood memory only now exists because of this picture? And, “You should see what’s there now?”

Among these many terrific Chicago and neighborhood groups that helped me find interesting content are: 1844 Chicago, Chicago L, Chicagoland History, Chicago Old Town in the ’60s, Chicago West Side Past and Present, Forgotten Chicago, Growing Up in Chicago, Historic Chicago, Illinois Central Railroad, Original Chicago, and Railroad History Buffs of Illinois to name just a few. Check them out, and join up if you’re curious. Get ready to bathe in the full range of images from deceptive AI fakes, to another yawn or something new, interesting, and completely surprising to your eyes.

Important Long Term Keepers of Chicago’s History

Let’s hear it again for the Ryerson and Burnham Library of the Art Institute of Chicago, the Newberry Library, the Chicago History Museum, and the Library of the University of Chicago. They are doing the hard and resource intensive work of capturing and celebrating the highs (skyscrapers getting taller), and lows (labor, racial, ethnic conflict) of our city’s culture and place in American life.

My friend Jan Grayson served for several years as Chair of the Board of Directors of the Chicago Architecture Foundation, the predecessor of the Chicago Architecture Center (CAC). Both Jan until his death, and my former law partner Jeffrey Jahns, have also been CAC Trustees Emeritus, so I’ve had direct knowledge of this organization’s exceptional work. It, and the Commission on Chicago Landmarks, both continue to be central players in calling the world’s attention to the special role Chicago has and continues to play in modern architecture.

Finally, A special call out is also due Chicagology, for it unique and important scholarship role in uniting contemporary newspaper accounts with architectural developments and events of a long-ago Chicago.

A Cliff Dweller's History of Chicago
A Narrative History of Chicago's Six ErasWilliam J. Bowe

Era History