This Halloween cruise on the Chicago River is creepier than Lower Wacker

What’s creepier than Lower Wacker? No, it’s not Lower Lower Wacker (though that is terrifying). In our book, the answer is First Lady’s Creepy Cruise.

This Halloween-themed cruise down the Chicago River offers 90 minutes of after-dark skyline views paired with disturbing stories of Chicago’s worst serial killers, gangsters and ghosts that still haunt Chicagoans today.

In my search for the best Halloween events and things to do this fall in Chicago, the name "Creepy Cruise" piqued my interest. So, on a recent Saturday night, I stepped on board to find out what makes this cruise so creepy. Spoiler: I quickly found out.

Boarding begins 20 minutes before departure, but by then, a majority of passengers had already queued up. Because First Lady’s cruises board on the Riverwalk between Michigan Avenue and Columbus Drive, the line to board sits just a few feet away from Lower Wacker, which is, in my opinion, a very creepy start to the experience.

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Much like a line outside of a haunted house, the narrow, snaking queue is filled with eager passengers excitedly chatting about how scary they think the voyage will actually be. My expectations for the fright factor of this experience weren’t very high, but I was happily proven wrong.

A staff member with a skeleton mask welcomed us on board, and everyone hurriedly looked for the best seats remaining. I found a spot at the front of the boat and settled in when I heard an eerie familiar tune: Tiny Tim’s 1968 song “Tiptoe Through The Tulips.” This was followed by a chain of bone-chilling boarding songs from horror movies like Backrooms and Insidious. It was clear that this was, indeed, going to be a creepy cruise. 

There are no bad seats on this tour, but for the best chance at a prime spot, opt for a Priority Boarding ticket ($51). Otherwise, General Boarding ($46) still leaves you with plenty of options, as everyone is guaranteed a seat outside. For the least obstructed views, try to snag a seat on the front half of the boat.

The enthusiastic tour guide shared several true stories that took place at some of the skyline’s most notable landmarks. We heard about the dark history of many sites as we passed them, like how the Reid Murdoch Building was used as a morgue after Chicago’s worst maritime disaster in 1915, as well as folklore tales and paranormal accounts that have been passed down through generations.

This is a family-friendly experience that's suitable for all ages. On a scale from creepy to scary, it leans heavily to the creepy end of the spectrum, pairing one of the best things to do in Chicago, an architecture cruise, with unnerving true stories about the city's darkest moments. If you’re in the mood to be spooked this Halloween season, look no further than the Creepy Cruise.

First Lady’s Creepy Cruise runs on Fridays, Saturdays and select Thursdays and Sundays through November 1.