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If you can take any page at random from Chicago's real-world history and somehow not find your mind brimming with stories and characters, you just aren't doing something right. This is a city steeped in blood and intrigue. Autocratic politicians, serial killers, badanss financiers, riots, visionaries, crime, fires, floods, winds, pestilence, famine, death and war...and all this without a single real-world vampire. The following works have been and continue to be essential in creating the ongoing myth that is Chicago: the White City.
Chicago Public Library's Digital Collections: In-depth (very in-depth) reports on Chicago's sewer/tunnel system, lakefront development and all sorts of historical topics.
Graveyards.com: Specifically, this site documents all the graveyards of the Chicago area. All the creepy site decor aside, it's a great look at some of the people who've lived in and built the city.
Prairieghosts.com: Believe it or not, this site has some great stories; they're not exactly checked for accuracy, but then we're playing a game about vampires. The site design is an abomination, however, and has been getting steadily worse. Most of their good articles are online, they're just not linked to from the front page (or the links are buried among all their "sponsors"). Click the link, and scroll down to where it says "ARTICLES FROM THE FILES OF GHOSTS OF THE PRAIRIE;" what remains of their front-page links are in that section.
Chicago-L.org: There's no group of people more dedicated to endless, pointless research than railroad geeks, and the weird fans of Chicago's El system are no different. In the course of documenting, say, why exactly the Brown Line is Brown, they manage to make a decent ad-hoc history of the city. That, and they've got a whole page dedicated to Chicago railway disasters, and who can't appreciate that?
The Sun-Times, Tribune and Chicago Reader: It's a fact that no matter how weird a game plot might be, chances are good that something even stranger has happened in real life. CWC Storytellers try to keep current news incorporated in the game, though sometimes it seems like the real world is stealing ideas from us.
City of the Century: Detailed. Very detailed. Excruciatingly detailed. This book is not for the faint of heart, but it has every detail one could imagine about Chicago up until the turn of the 20th Century.
Devil in the White City: A fine bit of pop history, this one's worth picking up at a bookstore. Or just stealing from the hundreds of people reading it on just about any El platform (or are they all reading the Da Vinci Code now?)
Of course, this game wouldn't be what it is if not for the inclusion of bloodsuckers, werewolves, ritual magic, cults, secret societies, ghosts and all manner of supernatural miscellany. Besides the World of Darkness and Vampire: the Requiem game lines, the Storytellers draw from these "real-world" sources on the occult.
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The Golden Bough: A wise man (that wise man being Kenneth Hite; see below) once said that bad anthropology makes for good gaming. If that's true, Frazier's legendary text here makes for some of the best gaming in the world.
Complete Idiots' Guides: No, seriously. They have these for everything you could ever want to know anything about, and the depth is just shallow enough that you get all the salient points about a subject, but not so dense that you spend your life reading it. The Complete Idiot's Guide to Voodoo is about the closest thing to an RPG supplement without actually being published by a game company.
And of course, there's game stuff. Fortunately for us, the World of Darkness setting encourages Storytellers to cherry-pick good ideas from almost any source, and in our case, other roleplaying games have been fair game for plot inspiration. Here's just a few sources to check out:
White Wolf: Well, duh. But The Wolf's site is a good place for keeping up-to-date on what's being released for the World of Darkness, and their forums are always good for a laugh, and occasionally a good source of ideas.
Steve Jackson Games: Their GURPS sourcebooks are among the most well-researched material written for roleplaying games, and are useful for people playing just about any game, whether or not it's one of theirs. Particularly good ones are GURPS Cabal, which is its own Byzantine occult conspiracy, and GURPS Voodoo, a surprisingly thorough look at the religion and mystic traditions surrounding it.
Pyramid Magazine: This could've been lumped in with SJ Games' stuff above, but it's just good enough to merit its own section. Really, anyone who plays in or runs roleplaying games should at some point subscribe to Pyramid. The crown jewel of its articles is Kenneth Hite's Suppressed Transmission.
Unknown Armies:
Chicago: Dark Requiem: Probably the longest-running live-action Vampire chronicle in the world, this is where a ton of Chicago's live-action gaming populace got started. C:DR is a Masquerade chronicle and is part of One World by Night. They play at the Echo Gallery on the second and fourth Saturday and first and third Thursday of every month.
Elysium on the Prairie: Our first sister game to the south, EotP is a Requiem chronicle set in fabulous Champaign-Urbana, Illinois. They play on the opposite Friday nights from us.
Danville:
Smoke And Mirrors: This is a Masquerade chronicle set in modern-day New Orleans, and has been playing for a few months longer than the White City. S&M plays at Saint John's Church in Evanston every Saturday night but the last one of the month.
Conspiratus Angelorum: A Dark Ages period Masquerade chronicle with perhaps the most dedicated player base and Storyteller staff out there. They normally play on the second anf fifth Sundays each month.