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Go Here: The Weird Chicago Tour

Weird Chicago Tours

Chicago’s may be known as “The Windy City,” but who cares about wind, besides oscillating fan enthusiasts, and who cares about them besides their moms? Chicago is also touted as the most haunted city in America, and that’s way more awesome. You know what else is awesome? Gangsters, red light districts and serial killers.

One of my favorite things about visiting a new city is learning the history and seeking out those places where evidence of the past remains, because if you’ll remember, the past was really weird, and the further back you go, the weirder and cooler it gets. I’m pretty sure there are no 2012 Chicago mobsters with names as cool as “Machine Gun Jack” right here:

Machine Gun Jack Pics
Getty Images

I’m pretty good at finding the old and weird stuff in NY because I grew up here, but finding that stuff in an unfamiliar place can sometimes be tough if you don’t have an expert tour guide. I’m also pretty stubborn about spending money on things I could figure out on my own, but I’m trying to get better about that, because it seems like a good step towards being an “adult,” and I’m almost 30. (Also because I routinely destroy my own belongings when I try to “fix” them without “knowing how.”)

In the spirit of leaving things to the experts and my plans to visit Chicago soon, I’m making a promise to book a spot on a Weird Chicago Tour  — their motto is “Ghosts, Gangsters and Ghouls of the Windy City,” and they claim to be “The Wildest, Weirdest, Creepiest, Sexiest, Weirdest Way To See Chicago.” That’s enough to sell me on the $30, 3-hour trip, because those adjectives also happen to be the tennets by which I try to live. What I can’t decide is which tour to choose:

Weird & Haunted Tour: Our Standard Tour is unlike any other tour in the Windy City! This is not just another ghost tour but a mixture of ghosts, gangsters and much more! Join the Weird Chicago Crew and experience America’s Most Haunted City and her many ghosts, crime spots and all around strangeness! We don’t just drive past Chicago’s spirit-infested places, we let you experience them first-hand, taking you into places that other ghost tours just dream about having access to! It’s going to be a tour of the Windy City that you won’t soon forget!

Blood, Guns & Valentines Crime Tour: Join us for a “Bloody Chicago” ghosts and crime tour as we explore gangland sites, death scenes and the city’s grisliest and most famous crime spots. We’ll revisit not only the Capone and gangster sites of yesterday but horrific tales of blood and horror from Chicago’s haunted past from the St. Valentine’s Day Massacre to famous gangster hangouts, death sites, murder scenes and much more! 

Devil & the White City Tour: The History, Mystery & Hauntings of American serial Killer H.H. Holmes & the Chicago World’s Fair of 1893! Holmes operated the infamous “Murder Castle” during Chicago’s Columbian Exposition and Locations on the tour include the “Murder Castle” site,  Remnants of the 1893 World’s Fair locations, murder sites, ghost stories and more! 

Weird Chicago True Crime & Serial Killer Tour: Join Weird Chicago for a walk on the dark side of the city during this grisly and chilling tour. This is not an ordinary crime tour but a look at the most depraved murders in the city’s history — and some of the darkest crimes ever committed. Take a trip back in time and revisit some of the bloodiest crimes of Chicago’s past. Includes death sites, crime scenes and haunts of some of Chicago’s most depraved killers.

Red Light District Sex Tour: Join us for a walk on the wild side of Chicago with this historical tour of “Sex in the Windy City”, including some of the sexiest spots around on an exploration of the kinky, freaky and little -known locations of the famous local sex industry. This is a wild and entertaining tour of the naughty side of Chicago. We will examine Chicago’s sexy past from the city’s original Red Light Districts, the World’s first Playboy Club, Adults-Only Toy Shops, S&M dungeons, and much more!

Okay, nevermind, I am obviously going on the sex tour, it has this disclaimer: This tour is for adults only, 18 and up, with ID required. Clothing, open minds & polite attitudes required!

Hopefully Weird Chicago will add another tour soon that would explain this image that I found when I searched for Chicago 1960s, because WT-actual-F:

Man In A Spring
Getty Images/ man-in-a-spring-for-some-reason.biz* (*not true)

Check out the tour schedule before you book your trip, and let me know if you want to carpool, because that’s creepy, and remember how I love creepy?

Disclaimer: I’m definitely not driving to Chicago with you, internet stranger. We’re just having a little banter, here.

Next Awesome Place: La Perla, San Juan

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