If you’ve been following my adventures for a while, you know I love three things: food, ghosts, and Chicago. So when I stumbled across a Facebook event for a haunted bus tour through the Windy City, I knew I had to go. A day filled with eerie stories, historic landmarks, and a good meal? That’s my kind of itinerary.
The tour ran from 10 AM to 4 PM and even included lunch—perfection. Since Chicago is only a five-hour drive from home, I packed my bags, grabbed my camera, and hit the road. We stayed in a charming little suburb, just ten minutes from the train station, which made exploring the city so easy. I have to admit, taking the “L” again gave me a bit of nostalgia—it’s such a classic Chicago experience.
Our haunted journey began at the historic Congress Hotel, a fittingly spooky place rumored to be one of the most haunted hotels in America. I was thrilled to see that our tour guides were the same pair I’d met years ago on a similar trip. It felt like a full-circle moment, especially since one of my favorite memories growing up was going on ghost tours with my mom.
🕯️ Historic Haunts & Chilling Stories
Our first stop was the Battle of Fort Dearborn plaque—a quiet piece of history with an unsettling past. Many believe the area is still haunted by the soldiers who died there. It gave me chills to stand where such tragedy once took place, especially since the plaque is one of the only remaining markers of that historic event.
Next, we visited the school once attended by Bobby Franks, the 14-year-old victim of Leopold and Loeb’s infamous 1924 murder case. Standing there, knowing what happened just down the street, was haunting in a very human way. The tragedy still lingers in the air.
Of course, no Chicago ghost tour would be complete without a stop at the site of H.H. Holmes’ “Murder Castle.” Even though the building no longer stands, one of its original basement walls remains as part of the current post office’s foundation. Tour guides shared stories of workers who refuse to go down there alone, citing oppressive, negative energy. I couldn’t help but get goosebumps just listening.
The conversation about Holmes’s mysterious death fascinated me—some believe he faked his execution, others that he switched identities. DNA testing hasn’t solved the mystery either, which makes his legend all the more eerie. I was genuinely shocked to learn he was allowed to be buried under concrete at his own request. The irony isn’t lost on me—his victims never got that choice.
Then came the story of Richard Speck, the murderer of eight nurses in the 1960s. Standing in front of the apartment where it all happened was truly unsettling. One of our guides even shared that her aunt had been the neighbor who heard the lone survivor cry for help. It’s a chilling reminder of how these stories are not just tales from history—they happened to real people, in real neighborhoods.
🍗 Lunch with a Side of Ghosts
After a morning filled with dark history, we stopped for lunch at The Great Escape Restaurant, known for its delicious comfort food and haunted past. The chicken and potatoes were absolutely divine—and as an Iowan, I can confirm their homemade ranch dressing was next-level good.
The owner even joined us to share a few of his own paranormal encounters at the restaurant. Employees have seen apparitions, heard unexplainable noises, and some refuse to enter the basement alone. During renovations, they even unearthed two pairs of buried hands. (Yes—actual hands!) Needless to say, I didn’t ask for a basement tour.
🌆 Final Thoughts
Between the food, history, and paranormal tales, this ghost tour was everything I could’ve hoped for. Chicago never disappoints—whether you’re there for deep dish pizza, architecture, or stories that give you goosebumps.
If you ever get the chance to take a haunted history tour, do it. You’ll walk away with incredible stories, a little more knowledge, and maybe even a few goosebumps of your own.
Cupcakes & Tea with Elizabeth 