The regular airmail Chicago stop was at Grant Park, but flying conditions near Lake Michigan were too often far from favorable. The conditions at and location of Checkerboard Field were much better.
During the early 1920s air mail operations at "Checkerboard Field" was moved across First Avenue to two longer runways used only for the air post operations. (Although this other field had another official name it was still referred to by most people as Checkerboard Field or as the Maywood airfield.) These runways were on the grounds currently occupied by the Edward Hines Jr. Memorial Hospital, where it remained until the post office turned over transcontinental routes to private contractors in 1927.
In 1923, Behncke sold the field to Wilfred Alonzo Yackey, a former military and airmail pilot. From 1923 until Yackey's death in an airplane crash, the Yackey Aircraft Company and Checkerboard Field were the center of aircraft manufacturing activities in the Chicago area.
From 1923 to 1927 the field provided air mail operations. It was also called Maywood Air Mail Field at this time.
The airmail company operating with Maywood Air Mail Field was the Robertson Aircraft Company. The company's chief air mail pilot was a Charles Lindbergh. One of Mr. Lindbergh's duties was to lay out the 285 mile route between Saint Louis to Maywood. The route included nine intermediate landing fields about every 30 miles. The intermediate landing fields were necessary due to the equipment and operating conditions of the day.
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