In some neighborhoods you can see where the street was raised but building weren't. There's a gap of a few feet between the sidewalk and the building where you can see down to the level of the original street and the former street level floor of the building now looks like a basement.
Off the top of my head you can see some buildings like this in the blocks North of Division between Ashland and the Kennedy.
I'm not 100%, but I don't think that's an example of the effects of the raising of the city. For one thing, the address is quite removed from the downtown area, but beyond that you can find these kinds of buildings all over the city, so I've always figured they were just built that way. Here's an example of a clearly recently-built building which has a similar design, in Wicker Park:
I can only guess but that could have been built that way to simply stylistically fit in with other building in the area, even if it wasn't necessary. Also, building it the way they did gives more light and access to the lower level and probably required less work.
Likewise I believe that many of the buildings in that area date to around the beginning of the 20th century, if not older which would put them in the right ballpark.
It is also not that far from downtown and very well within incorporated Chicago in 1900 (I'll have to look for earlier maps later).
Off the top of my head you can see some buildings like this in the blocks North of Division between Ashland and the Kennedy.
Here's an example from that area: https://www.google.com/maps/@41.9042461,-87.6638461,3a,75y,2...