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Amelia Earhart in Chicago, 1928
I know this must have been traumatic for the poor girl, but talk about aceing your final exam.
Aviatrix Elinor Smith piloted her plane under the Manhattan Bridge on her way to flying under all four East River bridges, October 20, 1928. Her plane is circled in red.
Photo: Nick Petersen for the NY Daily News via the NY Post

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One of the US Army's first female AH-64 Apache combat helicopter pilots, Leslie Herlick
Herlick entered flight school shortly after the U.S. military lifted the ban on women flying combat helicopters in 1993 and attended flight school at Fort Rucker, Alabama, from fall 1994 to May 1995. Following graduation in 1995, she was assigned to the 101st Airborne Division (Air Assault), becoming the first female warrant officer in her battalion.
Flying High