We've redesigned and expanded our page of guides to the city. Check it out, tell your friends, download them to a flash drive and save them for your grandkids because archaic guides to the city are fun. I've previously documented the seamy pleasures of Chicago Confidential ("In Chicago, however, the wenches seem flattered by these attentions, and will not resent them even though they may not necessarily take you up"), and thanks to Harold Henderson's Midwestern Microhistory blog I've found a bunch of much older guides in Illinois Harvest's online collection.
* The Standard Guide to Chicago, c. 1893. Fun back then: "While a young lady cannot very well see anything during a 'Slumming' Trip that is not repugnant to her finer sensibilties, and while she will see much that is shocking, or ought to be, to her modesty, yet she will learn that the path of vice is a thorny one, and that her fallen sisters are more in need of her pity than they are deserving of her scorn."
* Chicago by day and night : the pleasure seeker's guide to the Paris of America, c. 1892. "If, when confronted by the marvelously variegated array of recreations and pursuits that this great city has to offer, the stranger or the periodical visitor should turn away dissatisfied, imagining that he has failed to discover anything especially suited to his fancy, his mental and physical organism must be sadly askew. It is his fault and not Chicago's." The part about the "Cheyenne" is worth a read.
* Chicago sensations, or, Leaves from the note book of a Chicago reporter and detective. Kind of like Law & Order for Chicago c. 1886. See also Hands up! in the world of crime.
* So this then is the preachment entitled Chicago tongue, c. 1913. Not so much a guide as a treatise about gossip, but the title is amazing (more here). "Every large newspaper office is the scene of a seething discontent. Peace is never declared--war reigns eternally."