Feeling joyless in the real world, Josh and Melissa attempt to return to Schmigadoon but instead find themselves in the darker world of Schmicago.

As Josh makes a new friend in jail, Melissa hires a lawyer and goes undercover to clear his name.

While Josh spends time on the run with Topher and the tribe, Melissa explores Schmicago looking for clues and uncovers a family secret.

Will there be a happy ending? Josh and Melissa are presented with a life-changing choice.