Haunted Chicago Bar Crawl

In my 20s, I would often make the trip to Chicago and hangout in the various bars and clubs that populate my beloved Windy City. A particular favorite of mine was Exit on North Avenue. A club that catered to the punkers, goths and rivetheads of Chicago’s underground music scene. But, despite all of its trappings of darkness, there was one thing this bar was missing, a good ghost story. After all, you would think a place like Exit would at least have one ghost. Sadly, it did not.

Nevertheless, the same can’t be said for the other nighttime hotspots of Chicago. In fact, some of the city’s most haunted places are its drinking establishments. Here are five haunted bars where you can enjoy time out with friends and maybe even see a ghost.

The Green Mill Cocktail Lounge, 4802 N. Broadway 

If you’re in the mood for old time jazz while tossing back a few drinks, the world-famous Green Mill Cocktail Lounge is the place to find it. But if you look below the surface of its bright lights and upbeat music, this popular Uptown night spot has a dark history of murder and crime. And it wouldn’t be Chicago if Al Capone didn’t have his bloody hands in it.

The Green Mill was opened in 1907 and was originally known as Pop Morse’s Roadhouse. A few years after opening, ownership changed hands and it was renamed as The Green Mills Gardens. The new owners named it that as a nod to the famed Moulin Rouge of Paris, France. In the dry years of the Prohibition era, notorious gunman Jack “Machine Gun” McGurn, a member of Chicago’s organized crime syndicate called “The Outfit,” bought the bar and turned it into a place where a Chicagoan could find some illegal Canadian whiskey.

Jack McGurn, was one of those guys who didn’t like being told no. In fact, being denied anything in life typically sent the gangster into a violent rage. So, when Joe Lewis, a popular comedic singer refused to bring his act to the Green Mill, McGurn took it personally.

McGurn sent a small army of his guys into the city to hunt down Lewis and bring him to his bar for a little chat. When the entertainer was brought before the angry killer, McGurn slashed him across the throat from ear to ear. You know, to teach him a lesson. And that lesson was never to tell Jack McGurn “no.” Believe it or not, Lewis actually survived the vicious attack and learned the lesson quite well.

In its heyday, Chicago’s crown prince of crime, Al Capone, was a frequent visitor to the bar. Because of this a couple of modifications were made in the event the coppers came looking for him. A trap door under his favorite table was cut into the floor that led to an underground tunnel. Capone made several escapes down this subterranean tunnel to freedom. Capone’s booth is still where it stood almost a century earlier. One other thing remains from those days long since gone, The Green Mill is haunted.

Two phantoms from that bygone era of speakeasies and gangsters are said to still haunt the bar. The ghostly figure of a woman in a white gown has been spotted sitting at the piano as if she is about to perform. Aslo the sounds of footsteps and men’s voices are often heard coming from the tunnels under Capone’s booth. One of those voices is believed to be Capone himself making a hasty retreat from the law.

Fireside Restaurant and Lounge, 5739 N. Ravenswood Avenue

The Fireside, as locals call it, has been a mainstay of the Ravenswood neighborhood since 1904. For over a century, this northside restaurant has been a gathering place for mourners burying their dearly departed in nearby RoseHill Cemetery, another Chicago haunted hotspot.

According to staff and customers, the Fireside has experienced a fair amount of paranormal activity over the decades. The restaurant is believed to be a ghost magnet of sorts for the many entities that haunt RoseHill. And these ghosts have no problem making themselves known.

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Shadowy figures and disembodied voices are regularly heard here. However, there is one ghost that is exclusive to the restaurant, a former employee. One night, while making his way down the narrow stairs, he lost his footing and tumbled down the stairs breaking his neck in the process. It was a couple days before anyone found his cold, lifeless body lying crumpled on the hard basement floor.

Since that fateful accident, the man’s ghost has been both seen and heard walking up and down the stairs where he met his fate. He is said to bring with him a chilly breeze and a profound sense of sadness. If you spend the day admiring the tombs and gravestones at RoseHill Cemetery, you may want to stop at the Fireside for a meal, a beer and a ghost.

The California Clipper, 1002 N. California Avenue

Humboldt Park, a westside neighborhood with a thriving Puerto Rican community is our next stop on this ghostly bar crawl. The popular neighborhood hangout, The California Clipper is the haunt of a very alluring spectral young woman.

White ladies are ghosts typically found in British ghost lore. But the California Clipper is home to the phantom of a beautiful woman in a white 1940’s dress. The white lady can be found sitting at the bar or on the stairs leading up to the upstairs apartment. She has also been seen in the women’s restroom checking her hair and make-up in the mirror. When she’s seen, she abruptly vanishes. No one can say with any certainty who she was in life, but she is very much a part of the California Clipper.

Lottie’s Pub, 1925 W. Cortland Street

Lottie’s Pub on W. Cortland has long been a favorite hangout in the trendy Bucktown neighborhood. Much like several bars in the Chicagoland area, it’s history is steeped in the city’s criminal underground.

Way back in the 1930s, Lottie Zagorski converted the basement of her grocery store into a bar catering to the undesirables of Chicago. It was common knowledge that whatever your vice was, be it drugs, gambling or prostitutes, you could easily find it at Lottie’s place.

In 1967, Lottie and Andy “the Greek” Lochinous were arrested for running an illegal gambling den. To save herself from doing any jail time, Lottie threw the entire criminal underground under a bus by testifying to a grand jury. She told them everything she knew and every gambling den, gin joint and house of ill repute was put out of business. And as you might imagine, Lottie made a lot of enemies.

At this point, you might be thinking that Lottie had a target on her back as every hitman in the city sought to bag a snitch. Unfortunately for them, the most hated woman in Chicago died peacefully in her sleep. No one ever got to collect on Lottie Zagorski’s head.

The bar that bares Lottie’s name, opened in the 1980s after several businesses failed to make it work. Some people felt the building was cursed and soon they would find out their suspicions might just be correct. In 2004, while renovating the basement, a shocking discovery was made. A skeleton was discovered under the floorboards and although the identity of the remains were never ascertained, the discovery may have stirred up strange activity.

Since the discovery of the human remains, patrons and bar employees reported witnessing ghostly apparitions. One of the ghosts, believed to be Lottie herself, takes out her anger by throwing glasses and chairs around. Maybe Lottie isn’t pleased with the direction her establishment has taken.

Congress Plaza Hotel Lounge, 520 S. Michigan Avenue

Our final stop on this haunted Windy City bar crawl brings us to a familiar haunt, the Congress Plaza Hotel. This iconic haunt is considered to be Chicago’s most haunted place. Several ghosts are believed to haunt the Congress, but it’s the lounge that we need to concern ourselves with.

The luxurious hotel’s lounge is believed to be the domain of the apparition of a little boy from the early 20th century. When he’s seen, he is said to run around the lounge before getting on an elevator going up to the twelfth floor. When he exits the elevator, he vanishes and moments later reappears in the lounge innocently playing by himself. He’s believed to be the child of a former guest who died unexpectedly in the hotel. Sadly, his identity has been lost to history.

Chicago’s bars and clubs are a great place to relax and enjoy a night out on the town. If you should ever visit this great American city, the bars are always open serving up spirits, both alcoholic and spectral.

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About Rick Hale 33 Articles
Rick Hale became interested in anomalous phenomenon at an early age after encountering an apparition in his grandparent's home. Rick is the author of "The Geek's Guide To The Strange and Unusual: Poltergeists, Ghost and Demons," and "Behold! Shocking True Tales Off Terror...And Some Other Spooky Stuff." Rick has been published in Haunted Times Magazine, Paranormal Underground Magazine, The Supernatural Magazine, Spookyisles.com and Legends Magazine. Rick appeared in Ghost Tapes 2 and Ghost Tapes: The Series found at YouTube.com.
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