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There is magic and mystery in Chicago, aka the White City, Second City, and Windy City. The third-largest city in the United States, this tenacious Midwestern town has survived a Great Fire, organized crime, curses, and the Chicago Cubs’ abysmal 2003 loss to the Florida Marlins. It has charm, grit, and a whole lot of stories that make it a great destination. Whether you’re seeking tales about ghosts, gangsters, killers, or even cowboys, there is no shortage of stories to explore in Chi-Town. Read ahead for a varied list of favorites.
There seems to be as many ghost tours in Chicago as there are ghost stories, but paranormal author Ursula Bielski’s Original Chicago Hauntings bus tour rightly deserves credit as the best in the city. Bielski’s research spans three decades, and her tour (hosted by her, or by a staff historian and paranormal investigator) has garnered a quality reputation for 15 years. The nearly 3-hour tour makes stops at supposedly haunted sites of tragedies such as the Iroquis Theater Fire, the Eastland Disaster, the site of the original City Cemetery, and more. The tour also makes a visit to the infamous Hull House, home to many ghost stories, and said to be the inspiration for Rosemary’s Baby because of the urban legend of a devil child locked in the attic.
Resurrection Mary and the Archer Avenue Triangle
A little southwest of Chicago, the story of Resurrection Mary is nonetheless one of the most famous ghost stories of the Windy City – and in the nation. The tale, which dates back to the 1930s, is a classic one of a woman found hitchhiking along Archer Avenue. A driver picks her up, and as they approach Resurrection Cemetery, she insists upon being let out, and then disappears. Before he died in 2012, Chicago ghostlore historian Richard Crowe documented more than three dozen “substantiated” accounts of Mary, according to the Chicago Tribune.
The story also involves the colorful Chet’s Melody Lounge, an unpretentious bar (also said to be quite haunted) across the street from the cemetery, and the site of a cab driver who claimed to have just had Mary as his fare. For her part, Bielski of Chicago Hauntings is credited with having established the most reasonable explanation of Mary’s identity in 1999. In her tour, she discusses that, as well as the Archer Avenue Triangle — an ancient Indian trail also populated by stories of banshees, werewolves, and phantom monks.
The Devil in the White City
The story of prolific Chicago serial killer H. H. Holmes is the stuff of both fact, and fiction. It is indeed true crime, but so macabre that it belongs in the category of “Weird.” Active between 1891 and 1894, Holmes created a labyrinth of torture in the so-called Murder Castle (which included secret passageways, false walls, gas chambers, surgical tables for dissection, and body chutes that led to a basement with acid vats).
His story, and that of the 1893 Chicago World’s Fair, inspired the 2003 historical non-fiction book The Devil in the White City by Erik Larson. That book in turn inspires the Chicago Hauntings Devil in the White City tour that visits the World’s Fairgrounds, and the site of Holmes’ Murder Castle.
John Hancock Center
There’s a lot of weirdness going around Chicago to keep visitors busy. In 2006, a Chicago O’Hare International Airport was the site of a famous UFO sighting, which was well-documented by credible witnesses. Meanwhile the Mothman (a name given to the alien/angel/cryptid/interdimensional being associated with Point Pleasant, WV) has apparently become a Chicagoan based on a stream of sightings going back to 2011.
And yet, the imposing 100-story John Hancock Center deserves its own entry in the weird annals of Chicago. Renamed 875 North Michigan Avenue in 2018 (but forever known as the Hancock), this black monolith sits on land allegedly cursed by George Streeter, who tried to establish his own country – which was a shanty town built atop a garbage dump. The Hancock has seen a fair share of tragedy, including the deaths of Chris Farley, and falling scaffolding that killed three people in 2002.
Additionally, there are tales of baffling falling deaths that began three years after its completion in 1969. There are a lot of myths associated with the building (which was once the second tallest in the world). Lore persists that Anton LaVey, Chicago native and founder of the LaVeyan Satanism sect of the Church of Satan, was fascinated by the trapezoidal shape of the structure – which he believed could serve as a Lovecraftian portal to another realm. That perhaps influences the stories that Dana Barrett’s building in Ghostbusters (and home to the Cult of Gozer) was based on the John Hancock Center. Despite all the stories, of varying basis in fact, the Hancock is still a striking structure – with a famous lounge on the 96th floor that has 360-degree views of the city, and four states beyond.
Chicago’s connection to organized crime is an inseparable part of the city’s identity. And the stories of the mob continue to draw tourists to Second City even today. Names like Al Capone, The Untouchables, Hymie Weiss, and Bugs Moran still loom large.
Seemingly mundane locations are sites of famous shoot outs, such as the St. Valentine’s Day Massacre; or the Biograph Theater, where John Dillinger met his end. There are countless tours to explore the underworld of Chicago (sometimes literally, in the case of bootlegger tunnels), but Chicago Crime Tours has an impressive two-and-half hour exploration of crime that warrants a look.
Modern (Crime) Family
Organized Crime in Chicago doesn’t only revolve around tales of Prohibition, and Al Capone. Rather, there are more recent stories that extend into the 21st Century, such as those of Frank Calabrese, Jr., who was part of the Chicago Crime Syndicate — and a soldier in his father’s mafia army. Calabrese worked with the FBI to take down his father (as part of one of the nation’s largest mafia investigations), and his unfiltered Family Secrets bus tour is a firsthand account of life in the mob. The tour is led by the former wiseguy to sites where hits took place, and his crew ruled in Chinatown (along with stops in Little Italy, and Taylor Street).
The Blues Brothers Filming Locations
Home Alone. Eight Men Out. The Untouchables. Candyman. The Dark Knight. Pretty much every John Hughes movie. The Windy City has been the backdrop for an impressive amount of great (and sometimes not-so-great) films. But The Blues Brothers (1980) is part of the fabric of Chicago. The soul food café where Aretha Franklin sang was Nate’s Deli (since closed). The church where James Brown preached, and Jake and Elwood saw the light, is Pilgrim Baptist. Ray Charles’ Ray’s Music Exchange is Shelly’s Loan and Jewelry Co. The Blues Brothers live on in Chicago, as do many of the filming locations. Check out a guide to Blues Brothers filming locations here.
Ferris Bueller’s Day Off Filming Locations
Speaking of John Hughes, his 1986 film about a kid who just can’t with school on a beautiful day is as interwoven with Chicago as The Blues Brothers. As Ferris, Cameron, and Sloane enjoy the freedom of an unscheduled day off (and evade parents and Principal Rooney), audiences are taken on a virtual tour of the city. The Art Institute, Daley Plaza, Wrigley Field, Willis Tower, Lake Shore Drive, and so much more are featured – so much so that the city itself is a character in the film. And if you take your own day off in Chicago, you can retrace the steps of Bueller. Bueller. Bueller.
The Great 1,000-Mile Cowboy Race
Although Chicago is known for its history of gangsters, it does have a unique tie to the waning days of the Wild West. In June 1893 (the same year the aforementioned Murder Castle was in operation) a 1,000-mile horse race began in Chadron, Nebraska. Surrounded by a crowd of 3,000, nine horseman – with names like retired horse thief Doc Middleton, and Rattlesnake Jim, astride mounts with names like Poison – launched America’s longest horse race. The first to arrive at Buffalo Bill’s Wild West show in Chicago, next door to the World’s Fair which rejected the cowboy’s desire to officially exhibit at the show, would receive money from a prize purse and a gold-plated Colt revolver with ivory handle, and blue barrel.
The contest attracted concern from the humane society, and interest from Europe, as the men raced (and trotted) across the badlands of the Midwest to pre-approved check-in locations. Winner Joe Gillespie was actually the third man to arrive in Chicago 13 days later. The first, John Berry, couldn’t technically be declared the winner as he had planned the route. The second, Emmet Albright, was disqualified for shipping his horses by train for part of the route.
The story of the race is documented in Richard Serrano’s 2016 book American Endurance: The Great Cowboy Race and the Vanishing Wild West. Cody’s connection to Chicago runs deeper than the World’s Fair; his popular novel Buffalo Bill, King of the Bordermen was serialized on the front page of the paper beginning 1869, and he made his stage debut in the city in 1872. Also, abolitionist and women’s rights legend Susan B. Anthony stopped by Cody’s Wild West show during the World’s Fair, where she was treated as the cowboy’s guest, and he publicly rode his horse up to her box seats to offer her a dramatic bow.