Simon and K find themselves in over their heads when Uncle Spike causes their latest scheme to go south. Then, Officer Goodnight’s plans for the Chorale are overshadowed by the arrival of Kitty’s crooning ex.

While Simon and K work on their latest scheme, Turner’s surfaces with a saucy side-hustle of her own. Later, Allen’s attempts to fight for the people of the South Side catch the attention of Chicago’s elite.