Source: Emailed to Pegasus - Witness requested to remain anonymous

"Ron, Thanks for your speedy reply. Perhaps you've already seen this photo and know something about it. It was taken in Chicago I am told, but in 2005, not the recent incident. I don't know much of any other story about it.\

Here is all the additional info I could get on the Chicago UFO. 

"I apologize for the delay in getting back to you.  The camera used was an HP Photosmart R707 and the camera was on automatic settings at the time.  We were on route 80 West cutting through Chicago.  We were on the part of the highway near the trains.  Here is another picture taken minutes before or after the picture in question to give a point of relation.  I hope this helps. "

Thanks,
 

Comments:

Due to the lack of information accompanying the image it is almost impossible to make any determination. It does not however appear that this image has been tampered with. One of our other researchers had this to say...

"The camera used and at what setting, location and at what story/elevation would also help in removing a few more.

But if I have to guesstimate, I would have to include these variables:

If it is real:
the parameters of investigating should include bugs, birds, aircraft.
finding the elevation or what story/floor this was shot at could help eliminate most bugs
finding the area because of residencies would help eliminate almost all aircraft (albeit perhaps helicopters).

Misc variables:
Lets say it's the empire state building (we know that it's not but stay with me). We cannot exclude the possibility that a tourist or neighbor did not lose or throw a hat/item into or was a direct result of the wind. We also cannot exclude the possibility that this is a direct hoax.

Right now I would lean more towards bird than ufo because of the lack of any metallic or reflections
that are usually associated with a UFO