Ghost Busting in Chicago: The Interminable Midnight Tour

Bullet holes on Holy Name Cathedral mark the massacre of Earl “Hymie” Weiss in 1926.

It was a dark and stormy night… Well, it wasn’t stormy, but it was certainly dark as we stood on the corner of Monroe and Columbus Drive at 12 a.m. that chilly October night, our breath making mist in the air. It was the year 1998, and my roommate and I were excited to be embarking on a Halloweeeeeeny adventure. We held two coveted tickets to the Ghosts of Chicago tour. We had our choice of departure times, but we figured the midnight tour would be the creepiest.

I had known for some time that my roommate, Sarah P. Jenkins, would be into this kind of thing—she had just the right mix of supernatural curiosity and imagination, and I believe she had a touch of the sixth sense about her. I remember a story she’d shared with me a few weeks previous: She woke up one night to hear my cat, Miles, racing through the apartment hallway (as all cats love to do at 2 a.m.), his claws scraping excitedly on the hardwood floors as he scampered down the long stretch. “That’s cute,” Sarah thought, “He’s having a little nighttime romp,” and turned over in bed to find that Miles was fast asleep beside her. Let me be clear: only one cat lived in that house.

Sarah P. Jenkins also observed him raptly staring—eyes wide, pupils dilated—into the corners of the living room ceiling. For no apparent reason. And she enjoyed telling me about it. Was he tuning into phantom spirits of tenants past, Sarah wondered? Yes, she was the right person to bring along on a ghosty thrill ride through the city.

I wish I could say that the tour had been horrifically ghoulish. It wasn’t. Just horrifically grueling. An hour and a half would have been fine, but our guides managed to stretch the thing out for three painful hours. Sarah and I were still in our early 20s, but come 1:30 a.m. we were praying for it all to be over—we just wanted to sleep. Forever. It’s a terrible thing to feel like you’re being held hostage on a ride you paid a lot of money for.

Hymie’s Shrub

I do have a few distinct memories from that night. The first, I admit, was legitimately spooky.

During the dark days of prohibition, a gangster massacre had taken place on the steps of Holy Name Cathedral on State Street. North Side Irish gang boss Earl “Hymie” Weiss was apparently gunned to death by Capone’s men, who were shooting from the upper floor windows of a boarding house. In 1998, at the time of our tour, the boarding house had become the site of a parking lot surrounded by shrubs.

Our very serious guide and his even-more-serious female assistant led us out of the bus toward a bush that bordered Chicago Avenue. Our guide, we’ll call him Dennis—because I have no recollection of what his actual name was—reported that he regularly observed unexplainable “activity” near this particular hedge. And that maybe we’d get lucky tonight. (Oh my god, a haunted bush!) Being that it was our initial stop on the tour, our hopes were high for some firsthand horror.

Dennis explained that there are a few perceivable signs of a paranormal haunting. One of them is irregular electromagnetic activity and another is a sudden change in temperature—often in a very precise area. He then reverently showed us his trusted piece of ghost-busting equipment, a handheld electromagnetic reader with one of those red needles that moves across the face in an arc and goes wooo-wooo. He assured us, there was no logical reason why his gizmo should pick up unusual electromagnetic activity in the middle of a parking lot—over a bush. He extended his hand to take a reading. We held our breath. Sure enough, the needle moved. Wooo-wooo. Woooo-woooooo-ooo. Creepsters, right? As further “proof,” he held out his other hand to feel around for any “cold pockets,” as he called them. Waving it around over the shrub, he began to pause in a particular spot. Holding back a grin, he invited us, one by one, to pass our hands over the shrub to feel for ourselves.

Yes, I did. I swear I did. I felt the temperature change from cool to downright cold to cool again as I moved my hand through the air. Was it the ghost of Hymie Wiess? Or Al Capone, himself? We didn’t stay long enough to bust out a Ouija board and start asking questions. We had 40,000 other stops to make that night, so we had to push on.

Evidently, the base of the Hancock Tower is a ghosty hangout. A lot of people have jumped. I don’t like to think about it. “Gizmo” gave us no abnormal readings, however, and we felt no cold pockets, so we filed back onto the bus.

The reportedly haunted grave of Frances Pearce Stone at Rosehill Cemetery

We bumped along at a leisurely pace all the way up to the far north side and back again, doing drive-bys at the totem pole near the lakeshore path at Addison Street, Rosehill Cemetery, and the Biograph Theater, among others. In those wee hours we were forced to endure story after story and in-bus video after video. Our eyes were beginning to droop. It was warm on that bus. Tell me again, why had we chosen the midnight tour?

It was somewhere downtown near the Chicago River that they dragged us out for the final look-see of the tour. Wacker Drive near Franklin? I don’t really know. I had been dozing for some time.

A dank little footpath led us down toward the gurgling, murky water. The very serious assistant, we’ll call her Pam—because I have no recollection of what her actual name was—explained that yet another sign of paranormal presence is a foul stench. She suddenly held out her hand to stop us from moving. “Do you smell that? That disgusting odor?” I couldn’t help but remember that the river itself had recently been evaluated by ecologists, and had been upgraded in status from “toxic” to merely “highly polluted.” As I sniffed the air, I personally smelled no stench other than that of very, very dirty water. Sarah P. Jenkins, who was no longer amused by any of it, pointed to the ground near our feet and said, “Ummmm, the smell might have something to do with that dead, rotting pigeon.”

“Exactly,” Pam replied, with passion in her eyes, “EXACTLY!!

What?!? What did that mean? Was she implying that the pigeon had died because the vicinity was haunted? We still chuckle and guffaw about that one. What a weird night.

The Ghost of Theater Past

My favorite event from the entire evening occurred before the tour had even begun. Our bus was due to manifest out of the fog at any moment, and we were huddled in small clusters kitty-corner to the old Goodman Theatre, right in front of the entrance to the underground parking lot. We had forgotten that Brian Dennehy was in town starring in Death of a Salesman, and sure enough, there he came lumbering toward us from across the street, in a very Brian Dennehy way.

Sarah P. Jenkins and I were trained actors. We knew what to do: be cool and pretend like everything was totally normal. . . and then freak out afterwards. As we stood there, calm and collected, and totally professional, the cluster of people next to us suddenly recognized him coming toward us in the crosswalk. “Oh my God!” one lady exclaimed, making no effort whatsoever to be subtle. He passed by her as she stammered, “It’s . . . it’s . . . it’s what’s-his-name!”

The aging actor stopped in his tracks and slowly pivoted around to glare at our entire group, exempting no one. “That’s right,” he snarled, “ol’ WHAT’S-his-name.

Looming there, with moonlight reflecting off of his unnaturally broad shoulders and huge, neckless head, he was scarier than any of the ghosts we would later not be encountering. Talk about cold pockets.

Meredith Siemsen

Meredith, an Iowa native, was baffled when she earned her high school's writing award in 1993. It wasn't until twenty years later that she discovered she actually enjoyed wordcraft. (Too bad she's still a two-fingered typist.) Thanks for reading, friends!