I finally got a chance to check out the new location of the used bookstore Selected Works (big thumbs up; I love sweet-natured bookstore cats), and in their treasure trove of midcentury paperbacks I found the best guide to Chicago ever: Chicago Confidential (1950) by yellow-journalism geniuses Jack Lait and Lee Mortimer, two former Chicago newspapermen who moved on to become the editor and Broadway columnist, respectively, of the old New York Daily Mirror. It's seamy, offensive, and well-written--a rich period piece. Journalists used to have such a fantastic vocabulary.
On "dames": "Don't talk to girls sitting at bars in Rush Street cocktail lounges. They are 'hookers' or maybe girl friends of tough guys, waiting to be called for."
On elevators: "When the lift operator tells you to stand back, be sure and do it. For in case you have not noticed, Chicago's elevators have no safety doors inside. If you are too near the front, and someone gives you a shove from the rear while the car is traveling at high speed, you might get your arm cut off."
On flirting: "In many cities it is positively dangerous to flirt with strange women, especially in crowded business districts where you are in danger of being run in. In Chicago, however, the wenches seem flattered by these attentions, and will not resent them even though they may not necessarily take you up."
On nudes: "We don't know why we brought this subject up. Nudity is such a cheap commodity that you can tell us more about it than we can you."
On bad neighborhoods: "The Fifth Police District of Chicago has attained world-wide eminence. It is known to law-enforcement students around the globe. For it has, consistently year after year, the highest crime per capita known to man, having passed Casablanca's diabolical Casbah, about which a library of literature has been written and staged, in wonderment of its wickedness."
On the Everleigh Club: "There were two parlors, the Indian Room, decked in authentic Oriental furniture, deep rugs, onyx-wainscoted walls hung with damask draperies, and servants from India in native garb; and the Throne Room, which was a Bacchanalian place of regal revel such as one might well fancy a gay, rich potentate would build for frolics with his harem. In each of these there was a concealed orchestra befitting the atmosphere, and in ten other rooms of revelry in the rear of these were art works and music and dancing-space."