Wheeling
OKA red bar across a white field, with a red wagon wheel sitting on it. The village worked it out with Cook County Commissioner Scott Britton, who is an amateur vexillologist. The bar stands for travel, rail included, so it's a distant cousin of the Northwest Line. The wheel is where it goes wrong. Each of its eight spokes means a different piece of village history, and at pin size the whole thing turns into a red smudge.
See it on Flags of the World