Haunted River Boat Tour – Chicago’s Creepy History 

A spooky Chicago skyline- Photo: Jessica Mordacq
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As Seadog  Cruises’ season for tours along the Chicago River and lakefront come to an end, I had the thrilling opportunity to dive into some of the city’s haunted history. 

On a chilly October evening, I made my way to Navy Pier. Past the Chicago Children’s Museum and the Centennial Ferris Wheel sat three yellow speed boats, one of which would take me on a haunted river ride. 

Photo: Jessica Mordacq

Seadog  Cruises has taken over one million tourists and locals to gaze at the buildings and natural landscape of Chicago. The view of the cityscape is paired with a tour guide’s commentary on architecture, the pier and the lakefront, or in this case, the city’s spooky history. 

Photo: City Cruises

A line of people waiting for some scary stories made their way onto the boat’s ramp and down into one of the seats as the sun began to set over the Chicago skyline. Though some had on light jackets, many would pull on hats once we started cruising down the river, and later, speeding across the lake. 

A few passengers carried cups of beer or wine that they bought on Navy Pier, since all City Cruises are BYOB (and BYODog – if you do, your dog gets on the boat free, and your ticket is 15% off with the code “Doggy”). 

Photo: City Cruises

After boarding, two tour guides crept to the front of the boat with a sack full of something, which we’d later discover was candy. They were dressed as two mobsters, pretending to be on the run from the cops after stealing jewels, mistakenly hopping on a tour boat instead of their getaway vessel. 

While we waited for our boat’s turn to go through the lock and enter the Chicago River, the two improvised, crafting alibis in the chance that our boat was pulled over by the police. And they run through the usual rules: no smoke signals that might tip off authorities that hostage passengers need help (no smoking) and no waving your hands around for the same reason (keep your appendages in the boat at all times). 

Photo: Jessica Mordacq

Once the lock raised the boat to the correct height, the gates opened and we were off. The pretend mobsters took on the role of tour guides to “blend in,” and boy did they know a lot of history for two criminals. 

Weaving through the Chicago River, we hear about the SS Eastland, a boat that capsized in 1915 where we float now. At night, people have reported seeing ghost-like figures reaching up from the water where the ship went down. 

We listened to a story about the Iroquois Theater, where one of the deadliest single-building disasters in U.S. history occurred, second only to 9/11. In 1903, a spotlight explosion started a fire, resulting in 602 deaths. In what is now Chicago’s Nederlander Theater, cast and crew occasionally glimpse figures in the balcony or in clothes from the turn of the 20th century. 

Photo: Jessica Mordacq

Al Capone wasn’t left out of the collection of fatal Chicago events and the ghost stories that go along with them, as the tour guide’s costumes alluded. Some people have heard gunshots and men moaning at the site of the Valentine’s Day Massacre. 

As the sky turned dark and we left the river, we floated out into Lake Michigan – but not before stalling for the boat’s passengers to take photos of the lit-up Chicago skyline. The captain cranked the motor and the music as we accelerated down the shoreline and back, then parked at Navy Pier. As we exit the boat, we collect candy out of the mobster tour guides’ sack. 

Photo: Jessica Mordacq

Though Halloween, the season for haunting stories, will soon be over – along with Seadog’s season from April to October – Seadog  Cruises offers a range of captivating on-the-water experiences. 

The popular River and Lake Architectural Tour is loaded with information about the buildings you pass along the way. Get an up-close view during a 75-minute ride for $40.

Lakefront Speedboat Rides last 30 minutes along Chicago’s coast. For $28, enjoy a complete view of Chicago’s skyline. 

Experience the speed of City Cruises boats’ two 1400 HP engines on a half-hour-long, $45 Extreme Thrill Ride. Jet along the lakefront with 360-degree spins, sprinkled with historic narration. 

On Wednesdays and Saturdays during the summer, Navy Pier puts on a spectacular firework show. For $50, view it from the water for an hour on a Firework Cruise

Seadog  Cruises tickets are available online or at 1-888-345-3880.


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