September 27, 1910 – As 200,000 people look on, Walter L. Brookins circles his Wright biplane 2,500 feet above the city for a sustained flight of 20 minutes. Taking off from Grant Park, which was “black with humanity,” [Chicago Daily Tribune, September 28, 1910] the aviator thrills the crowd as he soars south to Twelfth Street, over the Loop to the Federal Building on Dearborn Street, and back over the lake. “Chicago looks for all the world like the picture on a postal card when you are 2,000 feet above it,” Brookins says at the end of the flight. “I could look down between my legs and see everything, but of course could recognize only a few of the buildings. I knew the federal building as soon as I saw it and I stopped my westward flight as I looked directly beneath me.” The next day Brookins would attempt a sustained trip from Chicago to Springfield in an attempt to outrun an Illinois Central passenger train starting simultaneously.