According to a MUFON report from 2011, a couple in Chicago may have photographed Mothman.
The married couple were taking pictures with a smartphone on August 22, 2011 when they captured the image. They say they didn't spot the strange figure in the sky when they were snapping the pics, but only noticed it later when going over the photographs. The photographer claims that when he enlarged the picture, distinctly bat-like wings became evident.
Two female students were getting dressed to go out for the evening when they saw a pair of large, round, orange eyes peering at them thorough their window. Their third floor window that is. The women stood in their apartment, frozen in shock as the creature hovered outside. They reported being overwhelmed with fear and felt like they were being eyed as prey.
At least six other students in the area also reported the creature. They described it as between 6 and 7 feet tall, dark grey to black in color with glowing eyes. They witnessed it ascend into the air and reported that its huge wings made a whooshing sound when it flew.
And the sightings continued. A young couple enjoying an evening walk on the night of October 14th also spotted the flying figure. Hearing a commotion amongst a group of people, the couple looked up in time to see what they described as a man with wings flying about 12 feet above them. One witness to the incident stated that the creature was perfectly silhouetted against the evening sky and reminded her of an immensely oversized Sugar Glider that she had seen back at her home in Tasmania, Australia.
"But they were nothing like the soft eyes of a glider. These glowed red! We saw it for about four seconds before it disappeared from view. At first, I thought I was looking at a man in a hang glider, but it was those bloody eyes that made me think otherwise!"
Sources: Mufon and UFO Clearinghouse.