MEN IN BLACK .- So far there have been 30 reported sightings of a large, flying humanoid in Chicago in 2017, three prior sightings that took place in 2011, one in 2016, and one from across Lake Michigan in Indiana from the early 2000s.  They've been reported out of chronological order, so we've put together a timeline of the reports, with links to the articles that describe them, to help you contextualize the sightings.  Most of the sightings have taken place in Chicago's lakefront area, within a few miles of Lake Michigan.
The current timeline:
  • Two friends are surprised by a weird, winged entity at the Goshen Dam in Indiana in the summer of 2000.
  • A suspicious winged entity is captured on camera, two roommates and their friends are terrorized by glowing eyes peeking through their window, and a college student sees a "man with wings" in 2011.
  • A man sees a large, winged humanoid perched on a lamppost in Cicero around August of 2016.
  • A man driving on interstate 294 sees what he thinks is a person turn into a large black bird on February 8th, 2017.
  • A semi truck driver reports strange medical maladies after spotting a flying humanoid soaring over a Chicago expressway on March 22nd, 2017.
  • A witness walking her 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 sees 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.
  • A family walking along the riverfront sees a flying humanoid cross over the William P. Fahey bridge within a week of the May 5th sighting.
  • A group of friends see two giant bats perform aerial maneuvers near Adler Planetarium on May 19th, 2017.
  • A married couple witnesses a large, black, bat-like creature with glowing red eyes near the intersection of North Wrightwood Avenue and North Lakeview Avenue on May 27th, 2017.
  • A woman and her boyfriend see a "large black flying man with wings" near 127th St. & Ashland Ave., also on May 27th, 2017.
  • Two different couples see a large, bat-like flying humanoid in the Lincoln Park area on June 3rd, 2017.
  • A jogger near the Navy Pier sees an enormous bat take wing and fly towards the water treatment plant on June 17th, 2017.
  • A couple, along with a crowd of people, sees a large, black, bat-like creature with humanoid features near the Adler Planetarium on June 23rd, 2017.  A second report received in early July confirms the sighting details of this report.
  • A police officer, along with the officer's partner and a group of civilians, sees a "dark black shadow with wings" standing atop a building before taking flight in the Auburn Gresham neighborhood of Chicago on June 29th, 2017.  An aspiring journalist later comes forward to corroborate the officer's story.
  • A security person taking a break outside of The Owl sees a bat-like humanoid flying over an empty lot across the street on June 30th, 2017.
  • A car full of friends on Lake Shore Drive sees a "giant flying bat" on July 20th, 2017.
  • A man sees an insect-like flying humanoid take flight from near the top of Willis Tower on July 24th, 2017.
  • A person headed home from work sees a large, bat-like creature perched atop a light pole on July 27th, 2017.
  • Two friends see a "huge black shape" gliding over the Albany Park/Lincoln Square area on July 29th, 2017.
  • A witness sees a flying humanoid over Elgin, Illinois, on August 1st.
  • A woman and her son are terrified by a "tall, dark humanoid" with membranous wings seen in a park near their home in Bolingbrook, Illinois, on August 2nd, 2017.
  • A woman and her husband photograph a "giant bat" in Melrose Park on August 4th, 2017.  In the same day, a witness walking with their children sees a similar creature in River Forest.
  • A couple are startled by a "large winged being...with bright red eyes" flying over Lake Shore Drive on August 9th, 2017.
  • A city employee sees a "giant owl" flying off of Chicago's Ohio Street Beach on August 10th, 2017.
To report a sighting, contact Lon Strickler at lonstrickler@phantomsandmonsters.com or call him directly at 410-241-5974; fill out UFO Clearinghouse's contact form to get in touch with Manuel Navarette; or reach out to us directly at The Singular Fortean Society through our contact page.

An interactive map of the sightings is available here.

Source:http://www.singularfortean.com/news/2017/6/10/a-timeline-of-the-chicago-flying-humanoid-sightings-so-far