Winged humanoid soars over Logan Square: Security guard’s late-night encounter in Chicago’s heart

On a calm summer night in Logan Square, a veteran security guard’s routine cigarette break became a brush with the unexplained. Just after 10:30 PM on June 30th, 2023, a bat-like humanoid glided silently above Milwaukee Avenue, its wings catching the glow of the streetlights before vanishing into the clouds. As reports of winged humanoids continue to ripple through Chicagoland, this encounter adds another piece to a growing mystery that refuses to fade.

I received an email from a witness in Logan Square, Chicago, who expressed a desire to discuss a sighting he had on Friday, June 30th, at approximately 10:30 PM. The witness works security at a bar called 'The Owl,' located in the 2500 block of N. Milwaukee Ave in Logan Square.

The witness stated that he was outside the bar, leaning against the wall while smoking a cigarette. He was alone at the time, with only a few other people walking along the street. He noticed a large, bat-like creature flying above the streetlights (approximately 60-70 feet away) over the lot across the street (in the photo below, you can see a building that has since been razed). As he focused on the flying anomaly, he realized it was actually a bat-like humanoid. The body measured about 5 to 5 ½ feet in length and was grayish in color, well-illuminated by the streetlights. The head resembled that of a human, but was much thinner and featured a pointed crest extending from the back (similar to a pterosaur, but shorter). The head was turned away from the witness, so he could not see its eyes or face. The body tapered towards the back, with short legs or appendages tucked underneath it, followed by a short, rounded extension that resembled a tail. The wings had a full span of approximately 8 to 10 feet and were attached along the body. Although the wings had a bat-like membrane, they were heavy, resembling those of a pterosaur. The witness observed that the being flapped its wings to gain speed and height, and then glided without making any sound. It moved swiftly above the streetlights across N. Milwaukee Ave before bursting upwards into the clouds. He was uncertain if there were other witnesses, as the being flew past quickly.

At the time of the sighting, the witness's phone was inside the bar charging, and he was very upset that he didn't have it, as he might have had time to capture a photo. He mentioned that he did not feel fear or foreboding; he was merely startled by what he witnessed. The witness was compelling, forthright, and did not embellish his account.

NOTE: This Logan Square sighting is consistent with other recent Chicago humanoid encounters, notably those from Lincoln Park and near O’Hare. The witness’s detailed description, particularly the gray coloration, pterosaur-like crest, and heavy wing structure, suggests either a consistent physical form or a projected appearance shared across multiple cases. Notably, the emotional response was calm curiosity rather than terror, echoing the reactions of other credible witnesses.

The behavior pattern, low glide, silent movement, and sudden vertical ascent, aligns with prior reports suggesting either advanced aerial control or interdimensional capability. The possibility that this being is gradually acclimating humans to its presence cannot be dismissed.

As I mentioned earlier, the witnesses I have spoken to have been very upfront, which is not the case with many other witnesses to unknown creatures. After conversing with this witness, I am starting to sense that this being is attempting to reach out to a broader audience without exposing itself too much. This is the first time I have begun to feel that sensation. This report was later picked up and reported by VICE, leading to wider coverage of the phenomenon. Lon 

HAVE YOU OBSERVED OR ENCOUNTERED THE 'CHICAGO MOTHMAN?' PLEASE SEND ME YOUR REPORT! USE THE REPORT LINK LOCATED AT THE TOP OF THE PAGE. THANKS! LON

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By Lon Strickler / Author Fortean Researcher

Lon Strickler is a Fortean researcher, author, and publisher of the syndicated 'Phantoms and Monsters' blog. He began the blog in 2005, which has steadily grown in popularity and is read daily by tens of thousands of paranormal enthusiasts, investigators and those seeking the truth. His research and reports have been featured on hundreds of online media sources. Several of these published reports have been presented on various television segments, including The History Channel's 'Ancient Aliens,' Syfy's 'Paranormal Witness', 'Fact or Faked: Paranormal Files,' and Destination America's 'Monsters and Mysteries in America.'

He has been interviewed on hundreds of radio & online broadcasts, including multiple guest appearances on 'Coast to Coast AM.' He was also featured on Destination America's 'Monsters and Mysteries in America' television show for 'The Sykesville Monster' episode. Lon has written 9 books and is currently the host of Phantoms & Monsters Radio on YouTube.

If you would like to support the newsletter, blog and my work, you can use one of the donation buttons on the blog or newsletter, or go to Paypal.com and use my email [email protected] as the payee. Thanks again. Lon

(Source: phantomsandmonsters.com; November 10, 2025; https://tinyurl.com/24kohd27)
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