Haunted Places in Chicago: A Tour of the City’s Most Spooky Sites

  • By: Timothy Rose
  • Date: 11 December 2023
  • Time to read: 19 min.

While the Cubs’ recent results have been more than a little scary, there’s a different kind of fright awaiting in the heart of Chicago. Beyond the roar of Wrigley Field and the glimmer of the Magnificent Mile lies a shadowy world where the past lingers in the present: Haunted Places in Chicago.

This tour isn’t for the faint of heart. We’ll venture into the city’s most spooky sites, where eerie tales and ghostly encounters are as much a part of the fabric of the city as its famed architecture. From the Congress Plaza Hotel, where spectral guests roam the halls, to the unsettling depths of the city’s historic theaters, each site brims with stories that blur the line between legend and reality.

Chicago, a bustling metropolis by day, transforms into a haunting ground by night. In this exploration, we’ll uncover the chilling narratives hidden within the city’s landmarks, where echoes of the past manifest in unexplained sights and sounds.

So, brace yourself for a journey through the spine-chilling corners of Chicago, where history haunts every shadow and each creaking floorboard could be a ghostly greeting from the other side.

Chicago - Credit Nimesh Madhavan
Chicago – Credit Nimesh Madhavan

One of the most famous haunted places in Chicago is the former home of H.H. Holmes, the country’s first serial killer. The site of his infamous “Murder Castle” has long been a subject of fascination for those interested in the paranormal. Other haunted places in Chicago include the Red Lion Pub in Lincoln Park, which is said to be home to countless ghosts, and the Congress Plaza Hotel, which is reportedly one of the most haunted hotels in the country.

For those interested in exploring the city’s haunted history, there are a number of ghost tours available. These tours take visitors to some of the most haunted places in the city and offer a chance to hear firsthand accounts of ghost sightings and paranormal activity. Whether you believe in ghosts or not, there’s no denying that Chicago’s haunted history is a fascinating subject that continues to capture the imagination of locals and visitors alike.

Historical Hauntings

Chicago is a city with a rich and often tragic history, and it’s no surprise that many of its most famous haunted locations are steeped in that history. From the Great Chicago Fire to the Eastland Disaster, there are plenty of events that have left their mark on the city and its people.

Murder Castle

In the late 19th century, Englewood, Chicago was home to one of America’s most notorious criminals, H. H. Holmes. Born Herman Webster Mudgett, Holmes was a con artist and murderer who operated in Chicago between 1891 and 1894. His most infamous creation was a building in Englewood, dubbed the “Murder Castle”. This three-story edifice was rumored to be a maze of trapdoors, hidden rooms, and chutes leading to the basement. While many of these tales were sensationalized by the media of the time, the building’s true purpose was far more sinister.

Murder Castle - credit Stephen Hogan
Murder Castle – credit Stephen Hogan

Holmes’s criminal activities peaked around the World’s Columbian Exposition in 1893. He lured victims, especially young women, to the Murder Castle, where they met their untimely end. The building’s design aided Holmes in his crimes, allowing him to move bodies discreetly and dispose of them. It’s believed that he sold some of the remains to medical schools. Despite confessing to 27 murders, Holmes was only convicted for one – the killing of his business partner, Benjamin Pitezel. Alongside his murderous endeavors, Holmes engaged in various scams, including insurance fraud and bigamy.

The aftermath of Holmes’s reign of terror left a lasting mark on Chicago’s history. After his arrest, the Murder Castle was set ablaze by an unknown arsonist, and while it was rebuilt, it was eventually torn down in 1938. Holmes was executed in 1896, but the tales of his crimes, especially those committed in the Murder Castle, continue to haunt the annals of American crime. The Englewood site, once a symbol of horror, is now occupied by a post office, but the memories of what once stood there remain chilling reminders of the past.

The Eastland Disaster

The SS Eastland, a passenger ship based in Chicago, was known for its tours on the Great Lakes. On the fateful morning of 24 July 1915, the ship was filled to its capacity with 2,572 passengers, many of whom were employees from Western Electric Company’s Hawthorne Works, excitedly heading to a picnic in Michigan City, Indiana. As the passengers boarded, the ship began to list to the port side. Despite attempts to stabilize it, at 7:28 am, the Eastland lurched sharply and rolled completely onto its side, resting on the river’s bottom. The tragedy occurred just 20 feet from the wharf, making it even more shocking.

The sudden capsizing trapped hundreds of passengers below decks. Heavy furniture, including pianos and bookcases, crushed some, while others were trapped by the water. In total, 844 passengers and crew lost their lives, marking it as the largest loss of life from a single shipwreck on the Great Lakes. Given the magnitude of the tragedy, it’s no surprise that tales of ghostly apparitions and eerie sensations have been reported in the vicinity of the disaster. Many claim to have seen ghostly figures of passengers, heard cries for help, or felt cold spots near the river where the Eastland met its tragic end.

Following the disaster, the Eastland was salvaged and sold to the United States Navy. It underwent renovations and was renamed USS Wilmette, serving primarily as a training vessel on the Great Lakes. After World War II, the ship was scrapped. The disaster had a profound impact on Chicago’s history and led to significant changes in maritime safety regulations. Today, the Eastland disaster serves as a somber reminder of the unpredictability of nature and the importance of safety precautions. Memorials and markers have been erected to honor the victims, ensuring that the memory of that tragic day remains alive in the hearts of Chicagoans.

St. Valentine’s Day Massacre

In 1929, Chicago’s North Side experienced one of the most brutal events in mob history. The St. Valentine’s Day Massacre saw seven members of Chicago’s North Side Gang executed against a wall by four men, two of whom were dressed as policemen. This violent episode was a result of escalating tension between the South Side Italian gang led by Al Capone and the North Side Irish gang led by George “Bugs” Moran.

Over the years, the site has attracted tales of eerie occurrences and spectral figures. Witnesses often report hearing phantom gunshots, muffled screams, and cries. Some have even spotted ghostly apparitions, believed to be the spirits of the men murdered that day. It’s said that they’re trapped, forever reliving their tragic end, searching for justice. Other tales mention shadowy figures appearing and disappearing suddenly, and the chilling feeling of being watched.

St. Valentine’s Day Massacre Site – Credit Stephen Hogan

The massacre marked a significant turning point in the gangland power structure of 1920s Chicago. It effectively weakened Moran’s influence but did not eliminate him completely. Capone, on the other hand, faced no direct consequences for the massacre but eventually met his downfall due to tax evasion. As for the massacre site, over time it changed hands and purposes, but the dark events of that day left an indelible mark. Many believe the restless spirits are a testament to the violence and betrayal experienced on that fateful Valentine’s Day.

Chicago’s cemeteries are also home to many haunted locations. Graceland Cemetery, for example, is said to be haunted by a woman in white who wanders the grounds. Meanwhile, the City Cemetery, which was located where Lincoln Park is today, is said to be haunted by the ghosts of Civil War soldiers.

Other haunted locations in Chicago include Death Alley, where John Dillinger was gunned down by the FBI in 1934, and the House of Blues, which was built on the site of Fort Dearborn. Visitors to the Historic Water Tower, which survived the Great Chicago Fire, have reported seeing the ghost of a young boy.

Overall, Chicago’s haunted history is a fascinating and sometimes chilling part of the city’s past. Whether you believe in ghosts or not, these locations offer a glimpse into the darker side of Chicago’s history.

Haunted Cemeteries

Graceland Cemetery

Graceland Cemetery is a historic garden cemetery nestled in the Uptown community area of Chicago, Illinois. Established in 1860, it spans 121 acres and serves as the final resting place for many of Chicago’s notable figures. The cemetery’s main entrance is located at the intersection of Clark Street and Irving Park Road. The cemetery’s landscape is adorned with a serene reflecting lake, winding pathways, and over 2,000 trees, making it a certified arboretum. The cemetery’s design showcases a variety of burial monuments, some of which were crafted by renowned architects, some of whom are also interred there.

Graceland Cemetery - credit Onasill
Graceland Cemetery – credit Onasill

The cemetery is not just a place of rest but also a place of legends and mysteries. Among the many tales associated with Graceland, one of the most haunting is that of Inez Clarke. Legend has it that Inez was a young girl who tragically died in the late 1800s. A life-sized statue of her was placed over her grave, protected by a glass box. Over the years, many have reported that the statue disappears during thunderstorms, only to reappear once the storm has passed. Some night-time visitors have even claimed to hear the soft sounds of a girl crying or singing when near her monument. Whether these tales are true or merely products of an active imagination, they add a layer of intrigue to this historic Chicago landmark.

Haunted Hotels

Chicago is home to some of the most haunted hotels in the United States. The city’s rich history and numerous tragedies have left behind a plethora of ghost stories, and many of these stories are centered around the city’s hotels. Here are some of the most haunted hotels in Chicago:

Congress Plaza Hotel

The Congress Plaza Hotel, situated on South Michigan Avenue across from Grant Park in Chicago, boasts a rich history that dates back to 1893. Originally designed by architect Clinton J. Warren as an annex to the Auditorium Theater, the hotel was linked to the theater by a luxurious underground passage known as Peacock Alley. Over the years, the hotel underwent multiple expansions, with the design and construction of these additions overseen by the renowned firm of Holabird & Roche. The hotel has witnessed many significant events, from hosting the Benny Goodman NBC Radio Show in the 1930s to serving as a training school for the U.S. Army Air Forces during World War II.

Congress Plaza Hotel
Congress Plaza Hotel

However, it’s not just the historical events that make the Congress Plaza Hotel noteworthy. The hotel is often cited as one of Chicago’s most haunted buildings. One particularly chilling tale revolves around room 1252. It is said that a Czech-Jewish refugee named Adele Langer, devastated by her husband’s disappearance, threw her two sons out of the window before taking her own life by leaping from the room, plummeting twelve stories to her death.

The Congress Plaza Hotel has seen its share of ups and downs, from hosting presidents and major events to enduring a nearly decade-long strike. Today, while it stands as a testament to Chicago’s vibrant history, the echoes of its haunted past continue to intrigue and mystify visitors, making it a must-visit for those interested in the city’s paranormal tales.

Drake Hotel

Nestled on East Walton Place, overlooking the serene Lake Michigan, the Drake Hotel stands as a beacon of luxury and history in Chicago. Founded in 1920, this iconic establishment was the brainchild of Tracy Drake and John Drake Jnr., who acquired the property from the estate of Potter Palmer. Designed in the Italian Renaissance style by the acclaimed firm of Marshall and Fox, the hotel’s majestic silhouette has become an integral part of Chicago’s Gold Coast skyline. Over the years, the Drake has seamlessly blended the residential charm of the Gold Coast with the commercial allure of Michigan Avenue, making it a central figure in Chicago’s social and political tapestry.

But the Drake’s reputation isn’t just built on its architectural splendor or prime location. The hotel has been a magnet for the world’s elite, drawing in heads of state, celebrities, and even members of European aristocracy. Names like Winston Churchill, Marilyn Monroe, Joe DiMaggio, and Princess Diana have graced its halls. Yet, amidst the glamour, whispers of the supernatural have also found a home here. Local legends speak of ghostly apparitions and eerie occurrences, adding a layer of mystery to the hotel’s storied past. The most famous ghost that haunts the hotel is the “Lady in Red.” The story goes that the woman was attending a New Year’s Eve party at the hotel in 1920 when she fell to her death from the roof. Ever since then, guests have reported seeing her ghostly figure roaming the halls of the hotel.

Today, while the Drake continues to be a part of Hilton Hotels Corporation, its legacy remains untouched. It’s not just a hotel; it’s a testament to Chicago’s rich history, a blend of luxury, intrigue, and timeless elegance. Whether you’re drawn by its history, the tales of hauntings, or simply the allure of afternoon tea in the Palm Court, the Drake promises an experience like no other.

Overall, Chicago is a city with a rich history and many ghost stories. Its haunted hotels are some of the most famous in the country, and they continue to draw visitors from all over the world who are looking for a spooky experience.

Notorious Ghosts

Chicago has a long and storied history of notorious criminals, and it’s no surprise that some of their ghosts are said to still haunt the city. Here are a few of the most famous:

Al Capone

Al Capone, the infamous gangster who ruled Chicago’s underworld during the Prohibition era, is said to haunt several locations in the city. One of the most famous is the site of his former headquarters, the Lexington Hotel. Capone’s ghost has been reportedly seen in the hotel’s lobby and on the 10th floor, where his suite was located.

John Dillinger

John Dillinger was one of the most notorious bank robbers of the 1930s, and his death at the hands of the FBI is still shrouded in mystery. His ghost is said to haunt the alley where he was gunned down outside the Biograph Theater, which is now the Victory Gardens Biograph Theater.

Peg Leg Johnny

Peg Leg Johnny was a notorious Chicago gangster who was killed in a shootout with police in 1923. His ghost is said to haunt the site of his former speakeasy, the Green Mill Cocktail Lounge. Visitors have reported seeing his ghost sitting at the bar, smoking a cigar.

Leopold and Loeb

Nathan Leopold and Richard Loeb were two wealthy University of Chicago students who committed one of the most infamous murders in American history in 1924, when they kidnapped and killed 14-year-old Bobby Franks. Both men were sentenced to life in prison, but Loeb was killed by a fellow inmate in 1936. Leopold was eventually released from prison in 1958 and lived the rest of his life in Puerto Rico. The ghost of Bobby Franks is said to haunt the site where he was killed, while the ghosts of Leopold and Loeb are said to haunt the prison where they served their sentences.

Chicago is home to many other notorious ghosts, but these are some of the most famous. Whether or not you believe in ghosts, these stories are a fascinating part of the city’s history.

Haunted Landmarks

Chicago is a city with a rich history, and many of its landmarks have a spooky past. From theaters to cemeteries, there are countless places in the city that are believed to be haunted. Here are some of the most famous haunted landmarks in Chicago.

James M. Nederlander Theatre

Adjacent to the James M. Nederlander Theatre, formerly known as the Oriental Theatre, lies an alley with a dark and haunting past. This alley, also known as Couch Place, was the site of the tragic Iroquois Theatre fire in 1903. On December 30th, during a sold-out performance of the play “Mr. Bluebeard,” a stage light sparked, setting the highly flammable backdrops ablaze. Panic ensued as the audience scrambled to escape, but many found themselves trapped due to poorly designed exits and unfamiliar locking mechanisms. The fire lasted a mere thirty minutes, but in that short span, 600 lives were lost. Many of the victims were found piled in the alley outside the theater, leading to its grim moniker, Death Alley.

James M. Nederlander Theatre – Credit Warren LeMay

Since the tragedy, numerous reports of paranormal activity have emerged from the alleyway. Visitors often speak of an unexplained chilly breeze, even on the warmest of days. Whispers, seemingly calling out names, can be heard, and some have felt unseen hands resting on their shoulders. These phantom sensations have given rise to tales of restless spirits, perhaps those of the fire’s victims, still lingering in the place of their untimely demise.

Today, while the Nederlander Theatre stands as a testament to Chicago’s vibrant theatrical scene, the adjacent Death Alley serves as a somber reminder of the city’s tragic past. The haunting tales and eerie experiences reported by those who venture into the alleyway keep the memory of that fateful day alive, ensuring that the victims of the Iroquois Theatre fire are never forgotten.

John Hancock Center

The John Hancock Center is a renowned skyscraper located in Chicago, Illinois. Standing tall at 1,128 feet, this 100-story structure is an iconic part of Chicago’s skyline. Designed by the talented duo, Peruvian-American chief designer Bruce Graham and Bangladeshi-American structural engineer Fazlur Rahman Khan from Skidmore, Owings and Merrill (SOM), the building was a marvel of its time. When it reached its peak height on May 6, 1968, it was the world’s second-tallest building, surpassed only by the Empire State Building. The John Hancock Center is not just an office space; it houses restaurants, around 700 condominiums, and was once the residence with the highest altitude globally.

However, beyond its architectural significance, the John Hancock Center has had its share of eerie incidents and stories. The 1988 film “Poltergeist III” was set in this very building, adding a layer of cinematic spookiness to its history. Moreover, there have been various incidents over the years, from fires breaking out in apartments and cars to elevator malfunctions that have led to dramatic rescues. While not explicitly paranormal, these events have contributed to the building’s mystique and the tales that surround it.

Red Lion Pub

Located in the Lincoln Park neighborhood of Chicago, the Red Lion Pub is a British-style tavern known not only for its cozy atmosphere and extensive book collection but also for its reputation as one of the most haunted places in Chicago. The pub, originally built in 1882, has a rich history and has undergone several renovations over the years.

Many patrons and staff have reported unexplained phenomena at the pub. Some claim to have seen apparitions, including that of a woman in a white gown believed to be the ghost of a woman who died in the building. Others have reported hearing disembodied voices, footsteps, and even the sound of children playing when no one is around. The pub’s second floor, where many of the reported sightings occur, is said to be particularly active.

The owner, John Cordwell, has embraced the pub’s haunted reputation, often sharing stories of the various spirits believed to reside there. From a mischievous ghost named “Sharon” to the spirit of a former bartender, the tales of the Red Lion Pub add a layer of intrigue to this historic establishment.

If you’re interested in learning more or experiencing the pub’s eerie atmosphere for yourself, a visit to the Red Lion Pub might be in order. Just be prepared for some unexpected company from the other side!

Jane Addams Hull House

The Jane Addams Hull House in Chicago, Illinois, was co-founded in 1889 by Jane Addams and Ellen Gates Starr. Located on the Near West Side of Chicago, it was established to serve the recently arrived European immigrants. By 1911, Hull House had expanded to 13 buildings, offering a range of innovative social, educational, and artistic programs. Over the years, Hull House became a beacon for social reform, influencing urban planning, child labor laws, women’s suffrage, and other progressive initiatives.

Jane Addams Hull House - Credit Chicago Architecture Today
Jane Addams Hull House – Credit Chicago Architecture Today

The Hull House has its share of ghostly tales. Jane Addams herself noted that the building had a reputation for a “haunted attic.” Over the years, stories of ghosts and hauntings have made Hull House a popular stop on many “ghosts in Chicago” tours. One legend from 1913 tells of a child born with devilish features after a man claimed he’d rather have the Devil in his house than a picture of The Virgin Mary. The mother supposedly took the baby to Hull House, where Addams tried to have it baptized and ended up locking it in the attic. Another tale speaks of a “woman in white” ghost seen in one of the front bedrooms on the second floor.

Despite its haunted reputation, the Hull House’s impact on society was profound. It played a pivotal role in social reforms, offering services like public playgrounds, bathhouses, and public gymnasiums. The Hull House Association continued to provide social services throughout Chicago until 2012. Today, the original Hull House building stands as a museum, part of the College of Architecture and the Arts at the University of Illinois Chicago, preserving the legacy of Jane Addams and other resident social reformers.

Tonic Room

In the heart of Chicago, the building housing the Tonic Room has roots that stretch back to the Roaring Twenties. This establishment was not just a casual hangout; it was a favored spot for the city’s Irish mob and even operated as a notorious brothel. Over the decades, the walls of this place have absorbed tales of intrigue, crime, and passion.

The paranormal activity in the Tonic Room is as rich as its history. Numerous ghost sightings have been reported, especially in the bar area and the basement. The most spine-chilling discovery was made by the current building owners who found a painted pentagram on the basement floor and Egyptian symbols adorning the ceiling. These eerie symbols led to speculations that the Tonic Room was once a secret meeting place for the Golden Dawn, an organization deeply involved in the study of the occult. A woman even claimed to have witnessed a ritual murder during one of these clandestine meetings in the 1930s.

Today, the Tonic Room stands at 2447 N. Halsted Ave in Lincoln Park as an artistic lounge. It hosts live bands, comedians, and DJs, entertaining crowds who are mostly unaware of the site’s haunted past. While the music plays and laughter fills the air, the spirits of the Tonic Room continue to linger, reminding visitors of its otherworldly history.

Chicago Water Tower

Chicago Water Tower, a gothic structure of yellowish Joliet limestone, holds tales from Chicago’s vibrant past. Constructed in 1869, it’s one of the few structures that survived the Great Chicago Fire of 1871. Designed by architect William W. Boyington, this tower symbolized the city’s resilience and spirit.

Dusk brings whispers of its ghostly resident: the Unknown Fireman. Legend says, during the 1871 fire, this lone fireman tirelessly pumped water, trying to save the tower. Exhausted, he climbed to the top, only to witness the vast devastation below. Unable to bear the sight, it’s said he took his own life. Nightly, his silhouette is sometimes seen, forever on duty, protecting his beloved city.

Today, the tower stands strong amidst modern skyscrapers, a testament to Chicago’s history. While it now serves as a visitor’s center, many come for more than just the architecture. They hope for a glimpse of the Unknown Fireman, forever reminding us of the sacrifices made during that fateful fire.

These are just a few of the many haunted landmarks in Chicago. Whether you believe in ghosts or not, these places are sure to give you a spooky thrill.

Eerie Events

Chicago is known for its rich history and vibrant culture, but it is also home to some of the most haunted places in the country. From bars to cemeteries, Chicago has its fair share of spooky locations that are sure to give you goosebumps. Here are some of the eerie events that have taken place in these haunted places:


Halloween is the perfect time to visit some of Chicago’s haunted places. The city offers a variety of spooky events, including haunted house tours, ghost walks, and Halloween parties. One of the most popular events is the annual Halloween Gathering in Millennium Park, where thousands of people gather to celebrate the holiday with costumes, music, and performances.


Chicago has been the site of many supernatural events over the years. One of the most famous is the story of H.H. Holmes, the country’s first serial killer, who built a “murder castle” in the city’s Englewood neighborhood. Visitors to the site have reported seeing ghostly apparitions and hearing strange noises.

Another haunted location is the Red Lion Pub in Lincoln Park. The pub is said to be haunted by the ghost of a former owner, who is known to move objects and turn lights on and off. The pub has also been the site of several unexplained occurrences, including glasses flying off shelves and doors opening and closing on their own.


While Chicago may not be known for its zombie sightings, the city does offer a unique zombie experience. The Zombie Army Productions hosts an annual event called the Chicago Zombie Pub Crawl, where participants dress up as zombies and visit various bars throughout the city. The event is a fun way to celebrate Halloween and experience Chicago’s nightlife.

Whether you’re a believer in the supernatural or just looking for a spooky adventure, Chicago has something to offer. From haunted houses to ghost tours, the city is full of eerie events that are sure to give you a scare.

Frequently Asked Questions

What are some of the most haunted places in Chicago?

Chicago is known for its haunted places, with some of the most famous being the Biograph Theater, the former home of serial killer H.H. Holmes, and the Oriental/Ford Theater. Other notable haunted places include the Congress Plaza Hotel, the Red Lion Pub, and the St. Valentine’s Day Massacre site.

Have there been any reported ghost sightings in Chicago?

Yes, there have been numerous reported ghost sightings in Chicago. Visitors have reported seeing apparitions at various haunted places throughout the city, including the Biograph Theater and the Oriental/Ford Theater.

What is the history behind the haunted places in Chicago?

Many of the haunted places in Chicago have a dark and tragic history. For example, the Biograph Theater is where notorious bank robber John Dillinger was shot and killed by FBI agents. The Oriental/Ford Theater was the site of a horrific fire in 1903 that killed over 500 people. The former home of H.H. Holmes was where he lured and murdered numerous victims during the 1893 World’s Fair.

Are there any guided tours of haunted places in Chicago?

Yes, there are several guided tours of haunted places in Chicago. These tours take visitors to various haunted places throughout the city and provide information on the history and ghost sightings associated with each location. Some popular tours include the Chicago Hauntings Tour and the Ghosts and Gangsters Tour.

What precautions should I take when visiting haunted places in Chicago?

When visiting haunted places in Chicago, it is important to take necessary precautions to ensure your safety. Visitors should always stay with their group and avoid wandering off alone. It is also recommended to bring a flashlight and wear appropriate clothing and footwear.

Can I visit haunted places in Chicago at night?

Many haunted places in Chicago are open to visitors during the day, but some locations also offer nighttime tours. However, it is important to check the hours of operation and tour schedules before visiting. Visitors should also be aware that some haunted places may have restricted access at night for safety reasons.

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