Chicago engineer Octave Chanute was a little-known pioneer whose glider designs and experiments at the Indiana Dunes, between 1896 and 1898, served as inspiration to the Wright Brothers. Chanute, shown in this undated photo at Miller Beach, died in 1910.

Unidentified plane, 1910.

The foot-powered sky bicycle, 1907.

In March 1929, the Chicago Tribune purchased this Sikorsky Amphibious plane to attempt a flight from Chicago to Berlin and back with a crew of three. The plane was named Untin Bowler, partly because a hunting bowler hat was said to protect a wearer if he falls.

Two planes race at a Chicago event during the 1930s.