A deliberate misspelling of Chi-town. Originally given as a tattoo to a customer who was too dumb to check the stencil (2007), then expanded into a massive free tattoo giveaway.
Heydumbass, you didn't check your tattoo, it says Chi-TONW not Chi-TOWN!
Pajama casual is a term used when working from home and preparing for a video conference. All business above the waist and your pajama pants down below.