The icon uses negative space to create an interlocking W and M surrounded by the L which is repeated in negative to form the "Chicago Loop" going around the centre. The shapes can also be read as buildings or streets.
The icon can be rotated 180 degrees to read exactly the same but in the colours are reversed.
As the icon is a strong image, the font and styling of the text have been kept low key. The font is Bank Gothic with the W, M and A modified to balance with the icon. This font was chosen as the shapes again reflect the "Chicago Loop" particularly the "O" and therefore create a harmony between the icon and text.