From the massacre at Fort Dearborn in 1812 to the famous gangsters of the Prohibition, Chicago is a city steeped in history—and not all of it is savory. Every neighborhood has its scary stories and sordid histories, and there’s no better time to explore the seamier side of Chicago’s past than on a blustery fall day as Halloween approaches. Wear something warm, bring a camera and someone’s hand to hold, and spend an evening finding out just how scary the Second City is.

There are a number of tour companies that run “haunted Chicago” tours, but your best bet is Weird Chicago. Their regular tours hit all the hot spots and famous hauntings, but they also have specialized tours ranging from “Ghost Hunter Thursdays” to the more risqué “Red Light District” tour. If your group is large enough you can even book a private tour—but whatever you do, book early. October is the busy season, and this is an experience you don’t want to miss.

The Weird Chicago tour bus picks up in front of the Hard Rock Café in downtown Chicago. The tours start later in the evening and can run for two or three hours, so grab a bite at any of the nearby restaurants before getting on the bus. Decked out with Halloween masks and pictures of famous ghosts and infamous denizens of the Windy City, the tour bus is a small refitted school bus. The tour makes enough stops that passengers can stretch regularly, so the less-than-plush transportation shouldn’t dampen a night of ghost-hunting.

Each Weird Chicago Tour travels to different locations, and the guides have been known to take requests from knowledgeable patrons. There are places like the site of the Eastland disaster and the Iroquois Theatre where you can get off the bus to get closer to the haunting. The tour guides encourage people to bring cameras when they get off the bus to try to capture evidence of the world beyond the veil, though some nights seem to have greater ghostly activity than others.

The guides themselves are what make the tour—professional ghost hunters who believe that there are genuine hauntings but retain enough skepticism to be believable. Clearly knowledgeable and full of great stories, they do a fantastic job guiding tourists and long-time residents alike through Chicago’s spooky and often bloody past. Even the most hardened skeptics will find themselves believing just a little bit as they hear about the terrifying past of the city around them.

Weird Chicago does run a Haunted Pub Crawl, but if you aren’t able to get tickets you can always go get a ghostly drink on your own; Chicago is full of bars and taverns with deliciously spooky histories. From haunted Chinatown restaurants to bars built in old Satanic churches, there are many watering holes with sordid histories—but for a true taste of Chicago’s past, head north from the Hard Rock to The Red Lion Pub in Lincoln Park.

The Red Lion is a classic English pub that packs a triple-punch of ghoulish delight. Directly across the street from the Biograph Theater where John Dillinger was shot, it—like the rest of Lincoln Park—stands on what used to be the Chicago City Cemetery, and is reputed to be the most haunted pub in Chicago. Patrons and staff have reported everything from the ghost of a little girl to a mischievous spirit who locks people in the upstairs bathroom, despite the fact that the door has no lock. The Red Lion, which recently underwent renovations, has a strong beer selection and a palatable menu full of British comfort food—if you still have the stomach to eat after spending an evening with Chicago scariest spooks.

Chicago has always been a city to claim its history proudly, whether it’s the soaring skyscrapers or the terrifying villains that stalked the alleys between. As the winds chill and the days shorten, there’s no better way to prepare for Halloween than to take in the dark side of this astonishing city. From tragic accidents to bone-chilling killers, there is more to Chicago than meets the eye—if you’re brave enough to look.

Weird Chicago Tours:
www.weirdchicago.com
reservations: (312) 943-5572

The Red Lion Pub:
www.redlionchicago.com
2446 N Lincoln Ave
Chicago, IL 60614
(773) 348-2695