A great city is both a social entity and physical artifact. These two Chicago classics tell the history of Chicago's physical development.
History of Chicago Public Works is known to library catalogs as Chicago, meaning that it takes quite a bit of effort to find. This nicely illustrated book has short chapters discussing such critical public works as the water system, street paving, tunnels and others. It is the first thing we pull out for anybody exploring these subjects. You can either read it or browse the pictures for fun.
The page or two on "raising the grade" is particularly valuable as explanations of this process are rare. The basic concept is that Chicago is flat, in many cases former swamp, meaning that the original land level is below the lake and river level. Furthermore, sewers need to flow downhill. Thus starting in the 1850s, the city started requiring property owners to elevate their properties so the sewers could do their job and drain the city.
Randall's History of the Development of Building Construction in Chicago in Chicago is not overly readable, but it is a great reference book. It is also fun to browse.
Randall catalogs every downtown building of even minor importance. He tells when it was built, the names it was known by, the architect and where to find photographs. Also given is the height of the buildings in stories and when additional stories were added. I never realized until finding this book that most early 20th story buildings have had two or three stories added to the top.
Randall generally tells the same information about all of the previous buildings on a site dating back to the Great Fire of 1871 and before. There is no other book even remotely like it, except the first edition done by Randall's father.