Spooky River Cruises Taking Sightseeing To The Next Level In Chicago
Chicago’s waterways hold more than just architectural wonders they’re flowing with ghostly tales and mysterious histories. The Windy City offers river cruises that blend sightseeing with spine-tingling stories, perfect for thrill-seekers and history buffs alike.
These spooky boat tours reveal Chicago’s darker side while you float along its iconic rivers, creating an unforgettable experience that’s both educational and eerie.
1. Moonlit Gangster Ghost Tours
Al Capone’s spirit supposedly still haunts the Chicago River, where many mob hits went down during Prohibition. This evening cruise takes you through the exact spots where gangland murders occurred, with guides dressed as 1920s mobsters sharing bone-chilling tales of betrayal and revenge.
What makes this tour truly special is the authentic crime scene photographs projected onto nearby buildings as you pass notorious locations. Many visitors report strange cold spots on board, even during warm summer nights.
The captain sometimes cuts the engines in particularly haunted areas, letting the boat drift silently while passengers listen for ghostly whispers. Complimentary “bootlegger’s punch” adds to the Prohibition-era atmosphere while you cruise through Chicago’s criminal past.
2. Eastland Disaster Memorial Cruise
July 24, 1915 marks Chicago’s deadliest day when the SS Eastland capsized in the Chicago River, claiming 844 lives. This somber cruise follows the exact path of the ill-fated ship, stopping at the disaster site where witnesses have reported seeing ghostly figures struggling in the water.
Paranormal investigators frequently join these cruises, bringing equipment to measure unexplained energy fluctuations. The tour includes rarely seen photographs and personal stories of those who perished, creating an intimate connection to this tragic event.
During the journey, participants are encouraged to leave flowers on the water at the accident site. The experience combines historical education with respectful commemoration, often resulting in unexpected emotional connections to those lost over a century ago.
3. Phantom Pirate Cove Adventure
Chicago’s little-known pirate history comes alive on this family-friendly but genuinely spooky cruise. Few realize Lake Michigan once harbored ruthless freshwater pirates who raided cargo ships and established hidden coves along Chicago’s shoreline.
Children receive treasure maps marking locations where ghost ships have been spotted over the centuries. The highlight comes when approaching “Deadman’s Cove,” where the boat’s lights mysteriously flicker and the compass spins wildly a phenomenon the crew swears isn’t staged.
The captain recounts the legend of Captain Midnight, a Lake Michigan pirate whose ghost supposedly appears during storms, warning sailors of danger. While designed to be accessible for younger adventurers, the historically accurate tales of maritime disasters and unexplained disappearances provide enough genuine chills to entertain adults too.
4. Speakeasy Spirits Night Voyage
Glide through Chicago after dark on this adults-only cruise highlighting the city’s Prohibition-era haunts. The boat itself is transformed into a floating speakeasy complete with password-protected entry and period-accurate cocktails served by bartenders in vintage attire.
We dock at three riverside locations where infamous speakeasies once operated, now reportedly haunted by patrons who met violent ends. At each stop, professional mediums conduct brief séances attempting to contact spirits from Chicago’s boozy past.
The most chilling moment comes when passing beneath Michigan Avenue Bridge, where the boat lights dim and passengers often report seeing shadowy figures walking along the riverbank exactly where police once ambushed rumrunners. Between ghost stories, guests enjoy jazz music and learn to mix authentic 1920s cocktails, creating an immersive journey through Chicago’s spirited history.
5. Supernatural Skyscraper Voyage
Chicago’s iconic skyline holds countless ghost stories within its soaring towers. This evening cruise positions you perfectly to see the exact windows of the city’s most haunted high-rises while paranormal experts share evidence of spectral residents.
The boat carries powerful spotlights that illuminate specific floors where recurring hauntings have been documented. Guests use provided binoculars to watch for shadowy figures that sometimes appear in supposedly empty offices after hours.
Most startling is the stop near the Drake Hotel, where the famous Woman in Red reportedly jumped to her death and now appears in windows facing the water. The tour combines architectural information with supernatural tales, creating an experience that makes you see familiar buildings in an entirely new light. Even skeptics find themselves scanning windows for unexplained movements by the cruise’s end.
6. Butchered at the Bridge Tour
Chicago’s historic bridges have witnessed countless tragedies, from construction accidents to mob executions. This specialized cruise focuses exclusively on the city’s most haunted river crossings, stopping beneath each one to share its macabre history.
Under the Wells Street Bridge, guides demonstrate how gangsters would hang rivals from the ironwork, leaving bodies dangling as warnings. Passengers frequently report hearing phantom splashes and screams when the boat idles at these execution spots.
The most unsettling moment comes at dusk beneath Kinzie Street Bridge, where the tour uses underwater cameras to show the riverbed where bodies were dumped and where divers have reported being grabbed by unseen hands. Special sonar equipment occasionally picks up unexplained movement in the water, adding scientific intrigue to the supernatural claims that make this tour uniquely disturbing.
7. Riverside Cemetery Twilight Float
Few realize that several of Chicago’s oldest cemeteries border directly on the river’s edge. This twilight cruise glides silently past these forgotten burial grounds that predate the city itself, some with graves eroding into the water after centuries of neglect.
Historical records reveal that numerous bodies washed into the river during the Great Chicago Flood, and guides share documented sightings of ghostly figures that appear to wade in the shallows near these burial sites. The boat provides special filtered cameras that supposedly capture spectral energies invisible to the naked eye.
The most compelling stop features the partially submerged Rose Hill Cemetery section, where groundskeepers refuse to work after sunset due to persistent paranormal encounters. This peaceful yet eerie journey offers a unique perspective on Chicago’s relationship with death and remembrance, revealing a hidden world that exists alongside busy waterways.
8. Candlelight Tales of River Rescue
Chicago’s brave river rescue teams have saved countless lives over centuries but couldn’t save everyone. This intimate candlelit cruise honors those who perished in the river despite heroic rescue attempts, with current and retired rescue divers sharing firsthand accounts of inexplicable experiences during recovery missions.
The boat stops at five documented drowning sites where rescue workers have reported paranormal activity. Guests receive electronic candles to place on the water at each location, creating a moving memorial that often triggers unusual electromagnetic readings on the equipment brought aboard.
Most compelling are the stories from veteran divers who describe being guided to victims’ bodies by unexplained lights underwater or feeling hands pushing them toward someone trapped below the surface. This respectful yet genuinely chilling cruise combines first responder experiences with documented phenomena, offering a unique perspective on how tragedy can leave lasting impressions beyond our understanding.
9. Phantom Photographers Midnight Cruise
Designed specifically for paranormal photography enthusiasts, this late-night cruise provides optimal conditions for capturing unexplained phenomena on camera. The boat travels with minimal lighting through Chicago’s most actively haunted waterways, stopping at locations known for producing anomalous images.
Professional ghost photographers provide technical guidance on capturing orbs, mists, and apparitions while explaining the science behind different types of manifestations. Participants frequently capture unexplainable light formations and figures that weren’t visible to the naked eye.
The highlight comes during the “blind shoot” segment, where all lights are extinguished and passengers photograph in complete darkness toward notorious haunting sites. The resulting images, examined together on board, often reveal startling similarities in what different cameras capture. Even skeptics find themselves questioning their beliefs when their own devices record inexplicable phenomena during this uniquely interactive supernatural experience.
