In this interactive map are over 2,000 captioned and geotagged historical photos of Chicago. From the first printed map in 1688 to the present, the photos show what vintage Chicago looked like as the location grew from a small settlement by founder Jean Baptiste Pointe DuSable’s trading cabin into a global metropolis. I’ve tried to put the photo pins in approximately the same location the camera must have been in when the picture was taken. So, any errant dates or locations are just my lapses and not any AI hallucinations of the day. Don’t miss the many aerial photos and maps linked to the pins above Lake Michigan or overlook being able to drill down into the deep architectural history of the Loop. It’s all quite a rich visual chronical. If you zero in on The Cliff Dwellers 200 South Michigan location at the southwest corner at Adams Street across from the Art Institute, you’ll find more than two dozen photos showing what this immediate neighborhood looked like before and after the Great Chicago Fire in 1871. To search the full library of all these photos by year, street address or building name, all the individual photos have been collected here in the Photo Archive’s Vintage Chicago album. On the Club’s current site was once architect Solon Beman’s 1885 Pullman Building. The Pullman Building is featured in this short video of The Cliff Dwellers club’s storied history, Annals of a Bygone Era.