I have always found the connection between the the remaining portion of the 1911 Northwestern Train Station (today  known as the Ogilvie Transportation Center) and its now very dated looking 1987 portion to be a marriage made in hell.
Seen on both the Canal and Clinton St. (this one) facades, the split is quite severe. Looking at this you would think these are two completely unrelated structures, but in fact, they are of the same and are completely interconnected. (When you are inside, you don’t realize that there are two sections.) Architect Helmut Jahn (whose work I have both loved, and hated) clearly made no effort blend the two exteriors together. Given that this was done during the later peak years of PoMo, there was not a single nod to the older structure. No matching up the line of the cornice or any other of the historic detail, not even an effort to use the same sidewalk materials. In fact, if you look closely, you can see where they just cut off part of the top of the detail on the column. While there may be 75 years that separate them, I would vote for an annulment.