There’s no better time to explore the seamier side of Chicago’s past than on a blustery fall day as Halloween approaches. Wear something warm, bring a camera and someone’s hand to hold, and spend an evening finding out just how scary the Second City is on a haunted tour of Chicago.
After the haunted tour of Chicago we have our favorite picks for the most haunted restaurants and bars to visit and if you are truly daring, the most haunted hotel to stay the night!
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From the massacre at Fort Dearborn in 1812 to the famous gangsters of the Prohibition, Chicago is a city steeped in history—and not all of it is savory. Every neighborhood has its scary stories and sordid histories. There is no better way to get the eerie details of the Chicago ghost stories than on a tour!
Weird Chicago Haunted Tour
There are a number of tour companies that run “haunted Chicago” tours, but your best bet is Weird Chicago. Their regular tours hit all the hot spots and famous hauntings, but they also have specialized tours ranging from “Ghost Hunter Thursdays” to the more risqué “Red Light District” tour. If your group is large enough you can even book a private tour—but whatever you do, book early. October is the busy season, and this is an experience you don’t want to miss.
The Weird Chicago bus tours pick up in front of the Hard Rock Café in downtown Chicago. The tours start later in the evening and can run for two or three hours, so grab a bite at any of the nearby restaurants before getting on the bus. Decked out with Halloween masks and pictures of famous ghosts and infamous denizens of the Windy City, the tour bus is a small refitted school bus. The tour makes enough stops that passengers can stretch regularly, so the less-than-plush transportation shouldn’t dampen a night of ghost-hunting.
Each Weird Chicago Tour travels to different locations, and the guides have been known to take requests from knowledgeable patrons. There are places like the site of the Eastland disaster and the Iroquois Theatre where you can get off the bus to get closer to the haunting. The tour guides encourage people to bring cameras when they get off the bus to try to capture evidence of the world beyond the veil, though some nights seem to have greater ghostly activity than others.
The guides themselves are what make the tour—professional ghost hunters who believe that there are genuine hauntings but retain enough skepticism to be believable. Clearly knowledgeable and full of great stories, they do a fantastic job guiding tourists and long-time residents alike through Chicago’s spooky and often bloody past. Even the most hardened skeptics will find themselves believing just a little bit as they hear about the terrifying past of the city around them.
Haunted Restaurants & Bars in Chicago
Weird Chicago does run a Haunted Pub Crawl, but if you aren’t able to get tickets you can always go get a ghostly drink on your own; Chicago is full of bars and taverns with deliciously spooky histories.
The Red Lion Pub
From haunted Chinatown restaurants to bars built in old Satanic churches, there are many watering holes with sordid histories—but for a true taste of Chicago’s past, head north from the Hard Rock to The Red Lion Pub in Lincoln Park.
The Red Lion (2446 N Lincoln Ave, Chicago, IL 60614) is a classic English pub that packs a triple-punch of ghoulish delight. Directly across the street from the Biograph Theater where John Dillinger was shot, it—like the rest of Lincoln Park—stands on what used to be the Chicago City Cemetery, and is reputed to be the most haunted pub in Chicago.
Patrons and staff have reported everything from the ghost of a little girl to a mischievous spirit who locks people in the upstairs bathroom, despite the fact that the door has no lock. The Red Lion, which recently underwent renovations, has a strong beer selection and a palatable menu full of British comfort food—if you still have the stomach to eat after spending an evening with Chicago scariest spooks.
Chicago’s Most Haunted Hotels
Some of Chicago’s notable haunted locations happen to be hotels.
There are plenty of ghostly tales of paranormal activity at several Chicago hotels and the best way to find the true stories is to investigate yourself. So, if you are brave enough to check into one of the below hotels, you can learn about Chicago’s spooky side firsthand.
The Congress Plaza Hotel
The Congress Plaza Hotel (520 S Michigan Ave, Chicago, IL 60605) was built in 1893 and is undisputed by most as the most haunted hotel in Chicago.
The building is rumored to have been mobster Al Capone’s headquarters. There have been reports that his ghost is frequently seen near his old suite on the 8th floor.
People also talk about “Peg Leg Jonny” who is said to have been killed in an alley behind the hotel and is known to cause mischief such as rearranging furniture.
There’s another story of two children who were pushed from a 12th-story window by their mother. It’s said all of these guests still roam the hallways of the Congress Plaza Hotel.
Guests have reported the elevators mysteriously stopping at the most haunted floors, blankets being pulled off them in the middle of the night, and sounds of whispering at the bottom of their beds.
Room 441 is considered the most haunted room in the Old Congress Hotel and has had the most ghost sightings, including the silhouette of a woman. Past guests of room 441 have reported objects being moved without being touched and the lights flickered on and off during the night.
Check out reviews of The Congress Plaza Hotel on TripAdvisor or find the best hotel rates at Hotels.com or Booking.com
The Drake Hotel
The Drake Hotel (140 E. Walton Place) is said to be haunted by the ghost of the Lady in Red.
It’s been over 100 years that this jilted lover has been roaming the hotel halls. The story that most tell happened on a long-ago New Year’s Eve. A woman discovered her lover or possibly it was her husband with another woman at a fancy gala.
The distraught Lady in Red then chooses to jump from a window on the 10th floor (some accounts say it was from the roof). She has since been seen roaming the hallways, and is most commonly seen on the 10th floor.
Chicago has always been a city to claim its history proudly, whether it’s the soaring skyscrapers or the terrifying villains that stalked the alleys between. As the winds chill and the days shorten, there’s no better way to prepare for Halloween than to take in the dark side of this astonishing city. From tragic accidents to bone-chilling killers, there is more to Chicago than meets the eye—if you’re brave enough to look.
Chicago Ghost Tours
The below ghost tours are with the company Get Your Guide. They offer great tour options. Below are a few of the best ghost tours in Chicago.
- Windy City Ghosts Haunted Walking Tour: Visit some of the city’s most chilling locations and learn about the ghosts of Chicago gangsters and serial killers who haunt these streets. Visit some of the city’s most haunted locations in the mysterious Lincoln Park neighborhood. Check out the creepy bathroom mirrors at Lincoln Park Zoo, home to the ghost of a Victorian woman in white. You’ll also learn about the spirit that haunted Al Capone in his final days.
- Gangsters and Ghosts 2-Hour Walking Tour: Explore Chicago from the perspective of ghosts and gangsters. Take a history-based guided tour and discover Chicago’s gangsters and ghost stories. See the city’s darker side as you walk through the famous Chicago Loop district. Visit haunted locations and old crime scenes led by historians. This Chicago ghost tour includes stops at the Congress Hotel, Death Alley, and the Palmer House.
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Beth Grimaldi is a freelance writer and jack-of-all trades who lives on the north side of Chicago.