Hit a stain is a slang term heavily used in Chicago which means to rob someone or get something without doing much. A stain is someone or something that is seen as an easy come-up. Due to the recent explosion of drill music in the US, Chicago slang terms started spreading nationwide. Hit a stain means the same thing as a 'hit a lick'.
Numerous rappers from Chicago have used the term 'hit a stain' in their songs. In Lil Reese's "I Need That" song, he says "I'll drop a n*gga hit a stain or two, run that I need this - And this my life, I don't give a f*ck about no diss". In Lil Mouse's 'Im 4real' song, he says "Call brooski when its time to hit a stain - If a opp in my lane he get changed". In Caleb James' – Savemoney Cypher song, Chance The Rapper says "Never hit a treflip but they can hit a stain quick".