Hometown ghost stories from Chicago

October 11, 2017 / Chicago

Chicago is known as one of the most haunted cities in the US. From the location of the infamous H.H. Holmes ‘castle’ to Bachelor’s Grove Cemetery, there’s no shortage of spooky places to explore if you’re looking to freak yourself out. And while you may have heard all the popular stories, we’ve asked Chicago driver-partners to share their real-life paranormal experiences in celebration of Friday the 13th and Halloween.

Read on (if you dare)…


When I was about 9 years old back in 1999, I had my experience with the Hat Man. I still remember this night as clear as day. It was around 10:30pm and my mother was giving my younger sisters a bath. I had got out of my bed to go to the kitchen to get a glass of water. When I looked to the left I saw this very tall dark shadow in front of me and immediately froze. I felt goosebumps all over my body and felt the hair on the back of my neck stand up. This shadow was wearing a tall top hat with a very wide brim and a trench coat. The shadow was slowly moving in the direction of my mother and sisters at the end of the hall. The shadow then stopped and looked at me. I ran back into my room and jumped under the covers, absolutely terrified. “The Hat Man” is a very dark shadow with no facial features, just pure darkness. I’ve talked to some of my riders about my experience with the Hat Man, and they have claimed to have seen the same shadow…Scary!


I grew up on a block with 2 haunted houses. One day, my friends and I decided to get a spirit board and use it at the house on the corner where an older lady had passed away. We started asking it questions when, all of a sudden, we heard the shutters on the side of the house start slamming shut. We all ran off the porch screaming. That’s when my brother and his friends jumped off the roof laughing at us, having slammed the shutters to scare us. Knowing that it was just my brother, we went back on the porch to play with spirit board again. This time, we heard a big bang from inside this abandoned house and all the shutters start slamming. We looked at my brother and his friends and asked if they were trying to scare us again. They all replied “no”. We all looked at each other and ran from the house as fast as we could. I haven’t been back to that house since that day over 15 years ago.


Once my sister and I were home alone. We were waiting for our mom to come home from work. Around the normal time of our mom’s arrival, we were in the basement den and we heard our very big and heavy front door open and close and my mom’s usual “Hello, I’m home.” We ran up to greet her and no one was there. The door was still locked. The car wasn’t out front. In fact, she ran late that evening and did not come home for at least another hour. By then we had locked ourselves in our room. As if that was going to save us from the ‘Honey I’m Home’ ghost!


On November 29, 2011, my dog Snuggles was howling in his sleep. It’s rumored that when dogs howl in their sleep it’s because they’ve felt the presence of a ghost. I immediately started snapping pictures of where the dog was sleeping and I caught the below picture of the backyard and was surprised to see what was on the camera. Once, while driving with Uber, I picked up a medium.  I asked her what she saw in the photo and she replied that this little boy died 45 years ago. She said that he is confused and still looking for his mom. The other figures in the picture are trying to take him on to whatever is after this life.


There is a stretch of road in suburban Chicago that is bordered by a cemetery on both sides. I was taking a rider home just after 2am when we came to an extremely foggy patch of the road adjacent to the cemetery. We slowed down and cracked the windows when we heard what sounded like elephants trumpeting and a girl screaming for help. As I backed up slowly we both smelled smoke and heard animals panicking. We were trying to call 911 but the calls kept failing. We left and pulled over at a coffee shop that was still open. A staff member explained that there was a train wreck in 1918 where animals and circus performers were killed, right next to the cemetery. We did some research and found that this is a common occurrence and many people have reported hearing and seeing the same sounds and smells.

If you’re looking for more scary stories, check out what other driver partners and riders have experienced in notoriously haunted cities around the US.