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.

After Josh and Melissa realize they need to find a happy ending for everyone, they try to make that happen—with unintended consequences.

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

Convinced they're well on their way to a happy ending, Josh and Melissa both rocket to fame in Schmicago and get embroiled in a deadly plot.