Chucktown refers to Charleston, South Carolina. Also known as The Chuck, Charlie-o, Chucktezzy, ect. Originally named Charles Town after King Charles, hence "Chuck"town. Not the West Virginian city of Charleston. Chucktown was also featured as a question on an episode of discovery channels Cash Cab, just for you West Virginians out there who disagree.
Person A: "Hey, kid, youse going to ChuckTown for lunch, or you gonna come with me to the Tsongas to watch our PWHL girls destroy Montreal!?"
Person B: I'll come with youse to Tsongas and then head to ChuckTown for lunch, kid!"
Person A: "Wicked pissa plan for the afternoon, kid!"
Person B: "I know, right!?"
A recently constructed town, adjacent to the eighties disco-town Funkytown, to provide housing for the aging cokeheads who are now fat and addicted to sugar.