A sketch made by the witness's daughter. (Image credit: UFO Clearinghouse)

A flying humanoid sighting reported to UFO Clearinghouse in May is the second such case that features the sighting of an unknown winged creature that month. According to the site, "This is the second such sighting in a week and also in the same general area. An interview with the witnesses is being arranged and all information will be posted on the site as soon as it is available."

The sighting was released by UFO Clearinghouse on May 26th, but the only other reported sighting of a flying humanoid occurred on May 5th, so it is assumed that this sighting took place around that date, unless there is another, yet unreported sighting that took place in May. If the other report to which UFO Clearinghouse is referring is the May 5th sighting, then it should be noted that the sightings took place approximately 16 miles apart.

I was out with my daughter and mother celebrating my daughter’s recent graduation and after dinner and some light shopping, we decided to go out and check out the newly opened Chicago river walk that had just opened after construction. We accessed the river walk via the entrance on Michigan avenue and walked east toward the lake, looking at the sights and enjoying the beautiful view.
As we passed under the Columbus Drive bridge, we heard this strange sound and my daughter said “Look at that!” As we looked up, we saw a large winged “person” flying just above the water and then pulling up and going OVER the bridge! It looked like a huge owl or even a bat, but completely black with the exception of the two large eyes that appeared red. I’m not sure if it was the actual color of its eyes or just the light reflecting off of them, either way it looked very spooky.
We watched it go over the bridge and then continue flying right above the water and out of sight. It didn’t seem to care of anyone else saw it, it just let flying above the water until it was out of sight. My daughter and me tried to get pictures of it, but by the time we took pictures. All we got were blurry images of mostly black. My daughter did sketch what she saw and I have included it in this email.
We have never seen anything like this before, it never flapped its wings while we were in sight. At first glance, it looked like a person in a wing suit, but I don’t think anyone would be suicidal enough to go for a stunt like that along the waterfront.
I have gone skydiving before and have seen demonstrations of wingsuits in the past. This lead me to rule out that this would be a person in one of those suits or anything similar as it would be a sure fire recipe for disaster.
This thing also had wings that did seem a bit like the wings on a bat, as they seemed to form one big wing from the back to the bottom of the legs and seemed more of a membrane than feathered wings like an owl.
There was no sound at all, just an audible whoosh as it flew over. It was up and over the bridge in a matter of seconds and then it was gone. We were a bit shaken up after this thing flew away, we didn’t know what it was that we had seen.

This is the eighth sighting of a flying humanoid on Chicago's east side within a few miles of Lake Michigan to occur this year, and the tenth since 2011. The sightings so far tend to take place in the evening and night hours, and in areas of relative isolation. We will continue to update this and all sightings as the story develops.

So far, the timeline of events is:

A suspicious winged entity is captured on camera, and two roommates and their friends are terrorized by glowing eyes peeking through their window in 2011.
A semi truck driver reports strange medical maladies after spotting a flying humanoid flying over a Chicago expressway on March 22nd, 2017.
A witness walking their dog in Chicago's Oz Park runs into a paralyzing winged being on April 10th, 2017.
Three separate witnesses report seeing an unidentified flying humanoid over Chicago between April 15th and April 16th, 2017.
A man fishing with his son on the banks of the Little Calumet in Chicago see a weird winged being after hearing an eerie, unexplained sound on April 27th, 2017.
A man and his son see a bat-like creature while out walking in Calumet Park on May 5th, 2017.
The sighting reported above.

Flying Humanoid Sighting Made by Chicago Family is Second in a Single Week in May