[WATCH] Ryan Henry Braces for Competition in ‘Black Ink Crew: Chicago’ Trailer Shawn Grant November 29, 2019 TV VH1’s hit reality series Black Ink Crew: Chicago is set to return and will catch viewers up with all of their favorite Windy City natives. The new season will see Ryan getting ready for competition as a new shop comes into the city. Charmaine will be opening a new female-owned shop, with the assistance of renowned British tattoo artist Jess Simpson. Meanwhile, Phor will be making his mental health a priority and Don is looking to expand on his acting career, while his wife’s health may become a major distraction for him and his family. You can see the new Super Trailer below and be sure to watch when this season debuts on Wednesday, December 4 at 8PM ET/PT.