When you're touring Chicago, a little background on its architecture can really help you spot the architectural highlights around you. To learn about the city's architecture, you can explore the city by various walking or bus tours of Chicago architecture, such as with my company Chicago Detours, or of course you can cuddle up with a good book. Here are some great introductory books on Chicago architecture.
"Lost Chicago" by David Lowe
Here you can start with learning about buildings that you cannot tour to at all - because they don't exist anymore! The city changes and grows, and part of that process is demolition. This book of Chicago architecture shows beautiful photography of the buildings that we have lost in the past, mostly to the wrecking ball.
"AIA Guide to Chicago" by Various Authors
This book is a standard reference for anyone wanting to learn about Chicago buildings. You can easily look up buildings by their neighborhood, and also scope out other cool buildings you might want to see while you are in that area. From old to new architecture, you can get all the basics on a building like the year built, architect, and striking characteristics about the building's design. This book also gives some great overviews of neighborhood history. Buildings are identified on maps, making it easier to plot out an exploration of an area. New versions come out only every few years, and the latest is fresh from 2014.
"Constructing Chicago" by Daniel Bluestone
This book approaches several elements of the Chicago landscape, including park design, churches, skyscrapers and civic buildings. Bluestone ultimately gives you an entirely new perspective for the social and cultural forces that have shaped how the Chicago landscape looks today.
Start with these necessary books on Chicago architecture, and then you can progress to books on Chicago architects, such as Louis Sullivan or Frank Lloyd Wright.