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No, I don’t mean driving down into the Loop during peak traffic hours, dodging fenders and offensive drivers. Freewheeling mayhem. An experience where all hairs stand on end. Even though I learned how to drive on the LA Freeways, I always feel like I’ve won an incomprehensible victory by the time I’ve made it from one side of downtown Chicago to the other. Chi Town’s expressways are a terror but have nothing on its history of violence and weirdness.

I first became entranced with Windy City by reading about its achievements and its relationship with Galena, Illinois, not its scary legacy of politics and murders. The wild times of the twenties gets most of the publicity, but the years prior to the turn of the century had its own high spots.

Murders from Chicago boasted a certain cache when it came to the modi operandi of its killers. The most famous is the serial killer who strolled around the 1893 Chicago World’s Fair. The horror of that lived on for years. When my mother attended the world’s fair decades later, she walked in terror of being snatched up by a killer or slaver.

I got the biggest chill reading about the serial killer who got rid of his victims by dissolving them in a vat of acid in his basement. Ugh.

One could say that the city was made rich on death. The major slaughter houses massacred so many cattle, dumping the wastes into the Chicago River, that the butchering rendered the smelly liquid from the city water taps brown and greasy. Ee-yew.

The infamous Whitechapel Club, where journalists hung out, enacted gruesome rituals. A Chicago bartender by the name of the Michael (Mickey) Finn is given the credit for concocting a lethal drink (chloral hydrate) to poison his enemies—hence the saying of slipping one a Mickey.

I still haven’t read a conclusive solution to the mystery of the Marshal Field heir shooting “accident” that begat a series of tap-dances to cover up the mess. One version has the Chicago scion getting shot by one of the legendary beauties of the Everleigh Club, the fanciest bordello in the city. The Everleigh sisters owned the crowns for the most elegant establishment in the country and were also known for their closed mouths. They had the healthiest, prettiest, most talented girls. No one ever tattled. This fact says a great deal about how frightening the two madams must have been as employers.

The story goes—well, one of them—that the sisters, Ada and Minna, trundled the bleeding Field, the Younger, out of the swanky social club and back to his house before his wife, children and straight-laced father got wind of the adventure. The scandal lives to this day but threats and gossip never stopped the Everleighs. They eventually retired as millionaires, traveled the world and settled down to become “model” matrons.

Having hailed from Galena, Illinois, now a burg of less than five thousand, it seemed impossible that Chicago once courted Galena, even invested in a railroad to join the two cities. It was true that Galena was a thriving boomtown when Chicago was still the mud hole that Native Americans called “stinky onion” or Chickagou/Checagou. Nice. Anyway, the name stuck and not to be outdone, Chicago pulled itself out of the mud by raising the city. Pullman was part of the effort when buildings were lifted out of the muck. Guests in the hotels stayed during the event and stated that they never noticed the procedure.

Galena faded as the lead veins gave out, decimated by the Civil War, but Chicago thrived, rebuilt itself and continues to do so today. Galena may have some of the best ghost stories and prettiest terrain, but Chicago knows how to rise above the macabre.

If you’re still hungry for something grisly, check out Mysterious Chicago Blog:


Next time: Something Not So Grim