A Gray Background indicates sample entries reprinted from Aviation Chicago Timeline.
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Chicago, the Aviation Capital
(from the Introduction)
Most people today consider Chicago to be an “aviation capital” only in its demonstrated ability to thoroughly disrupt air travel throughout the nation. Many who are older or have an interest in Chicago history realize that Municipal/Midway Airport was the nation’s aviation crossroads for decades.
1891 Chanute Publishes Aviation Information
In order to foster manned flight, Octave Chanute began publishing experimentally based articles about activity by researchers around the world. Starting in 1891, he wrote a series of articles which were published in The Railroad and Engineering Journal,[a ] of which he was the associate editor of the aeronautics section.
1892/06/06 First Chicago "L"
Chicago’s first elevated train began operation on June 6, 1892. Chicago & South Side Rapid Transit Railroad operated nearly 50 steam engines on an elevated track from a station at Congress Pkwy. and Wabash Ave. going south to the terminus at State St. and 39th St. (Pershing Rd.). By the following year, the line extended to Jackson Park for the World’s Columbian Exposition. Part of this line has been incorporated into the current Green Line.[1]
1896/06/07 Chanute Glider Flights
In the summer of 1896, Octave Chanute conducted hundreds of flights in kites and gliders of many different configurations. Chanute, who was already in his mid-60s, flew the gliders at Miller Beach on the Indiana Dunes along with his associates, August Herring and William "Bill" Avery.
1908/12 First Chicago-Made Airplane Flies
Iowa-native Carl S. Bates attended Armour Institute[a], in Chicago, where he was taught by Octave Chanute, among others. Bates started building a plane of his own, a smaller version of Curtiss’s plane. While trying to build airplanes, Bates discovered the need for reliable, lightweight engines so he built his own. He formed the Bates Aero Motor Co. which produced high-quality air and water-cooled engines.
1909/12 Chicago’s First Airplane Dealer and Airport
James Plew was one of those impressed with the Glenn Curtiss demonstrations at Hawthorne Race Track in the fall of 1909. Plew, who was a White Steam Motor Car dealer, also started selling Curtiss airplanes. He dedicated an entire floor of his four-story building to his aeronautic department.
Read more: 1909/12 Chicago’s First Airplane Dealer and Airport
1912/05/25 First Advertising by Airplane
In one of the first commercial uses of aviation, Farnum Fish flew from Chicago to Milwaukee. Sponsored by the Milwaukee Journal, Fish made the 93-mi. flight in his Wright B Flyer on May 25, 1912, over the lake but never out of sight of the shore. He dropped 7,500 handbills advertising Wisconsin’s Boston Store before he delivered four bolts of cloth and an “unofficial” mail delivery.
1912/07/14 Katherine Stinson Licensed
On July 14, 1912, Katherine Stinson became the 4th woman pilot (Federation Aeronautique Internationale license #148) in the U.S. after training at Max Lillie’s Flying School. Her flight test required flying figure-eights and climbing to an altitude of 500 ft. At the time of her licensing, Stinson was the only woman pilot in the country. Harriet Quimby and Julia Clark had both died and Mathilda Moisant had retired from flying.
1914/05 Lake Shore Airline Formed
Lake Shore Airline Formed In May 1914, several ACI members started Lake Shore Airlines with regularly scheduled flights between Lake Forest, Grant Park, and the South Shore Country Club.
1915/06/29 Vilas Pioneers Fire Spotting
At his summer home in northern Wisconsin, Lake Forest resident and aviator Jack Vilas took the Chief Forester on a flight on June 29, 1915.
1917/06 Great Lakes Forms Air Squadron
As commander of the Great Lakes Naval Training Center, Capt. William Moffett formed an aviation training squadron in June 1917. Moffett’s attitude on the importance of aviation was greatly influenced by his North Shore neighbors and ACI members, particularly William Wrigley Jr., Jack Vilas and Pop Dickinson.
1918/07/27 First Unattached Parachute
Floyd Smith filed a patent for the first unattached parachute on July 27, 1918. Born in Chicago, James Floyd Smith[a] and his wife, Hilder, worked as trapeze performers in a circus on the West Coast.[1] He built an airplane and in June 1912 received License #207.
1924 Laird Opens Chicago Factory
Following a painful business experience in Wichita, Matty Laird resolved never again to rely on outside investors to produce his designs. Over the next few months, Laird built up some capital by participating in exhibitions and ferrying news reporters to various events such as the Kentucky Derby and Indy 500.
1928 First Flying Club
A group of Chicagoans, some of whom had previously attended flying schools, were displeased with the high cost of learning to fly. They formed the 
Edgewater Flying Club as an alternative to provide lower cost flight lessons.
Edgewater Flying Club was a non-profit organization in which the participants paid a membership fee to share the purchase of equipment and other fixed costs. Charges for flight time were based on actual operating costs.
1930/06/25 Hangar Fire at Muncipal Destroys 27 Planes
On the night of June 25, 1930, an explosion and fire started at Municipal in Universal Airline’s hangar, which housed planes of its subsidiary Stout Air Services. The fire quickly spread to an adjacent hangar used by Gray Goose Airlines. Both hangars and a total of 27 airplanes were destroyed in the blaze.
Read more: 1930/06/25 Hangar Fire at Muncipal Destroys 27 Planes
1930/06/27 Alleged Mob-Related Hangar Fires
At 2:45 am Friday June 27, 1930, a night watchman discovered a fire in a hangar at Pal-Waukee Air Port. It destroyed one plane but quick action by the staff kept the fire from engulfing the hangar, unlike the Municipal fire a few days earlier that destroyed two hangars and 27 planes.
1932 Airline Pilots Strike Century Airlines
E.L. Cord, best known as the designer of the Auburn, Cord and Dusenberg automobiles, had started Century Air Lines in March 1931. Because Century didn’t have any air mail contracts to subsidize its operations it had to rely solely on passenger revenue.
1945/06/17 Field's Sells Ercoupes
Marshall Field’s announced it would become the first department store in the country to sell airplanes starting in the fall of 1946. In a deal with Park Aircraft Sales and Service, Oliver L. Parks operated a flight facility at Pal-Waukee selling and servicing Ercoupe airplanes. Parks and Field’s offered Ercoupe for sale in Field’s State St. store in the sporting goods department on the first floor.
1949-07-04 National Air Fair at O'Hare
Several days after the city changed Orchard Field’s name to O’Hare, the newly-formed U.S. Air Force brought the National Air Fair to the airport. On the Fourth of July, 1949, 145,000 people braved 102° heat for the exhibition.
2008/05/24 Oldest ATP Pilot Licensed
Chicagoan Howard Levinson, a month shy of his 85th birthday, became the most senior pilot to receive his initial Airline Transport Pilot License on May 24, 2008. He pursued the ATP, the license required to fly for the airlines, because it was the only fixed-wing license or rating that he didn’t have.