When it was first created, the Chicago Sky's original wordmark featured a bold font with a unique “C” shape to represent both “Chicago” and “Sky.” It also included two stars on either side of the lettering to signify excellence on and off the court—a nod to their home city's flag which features four stars representing significant events in its history. This design stayed consistent until 2013 when it was modified slightly by adding an additional star inside each letter C as well as thickening up some of the lines within them for greater visual impact.

In 2018, after 12 years with this same look, designers decided it was time for another refresh; introducing new colors (blue & orange) into the mix along with updated fonts that are more modern yet still maintain classic elements from previous versions like serif typeface used throughout text portion of the mark itself. Finally, there were subtle changes made overall shape so now instead of being rectangular-like now appears to be oval-shaped giving the whole thing a softer feel while still keeping the essence of what made people fall, in love, in the first place: a strong sense of pride belonging to something special!